Five Times Jeff Tried to Propose (And One Time He Succeeded)
Title: Five Times Jeff Tried to Propose (And One Time He Succeeded)
Author: edenofalltrades
Pairing:Jeff/Annie
Spoilers: I wrote the story before season 4 started airing but I edited it after that so there are some very minor spoilers from the first few episodes of season 4.
Rating/Warnings: Teen/PG-13. It’s fairly mild but there is minor course language, including one f-bomb.
Word Count: 5,772
Disclaimers: I do not own Community and will not be making any profit from this story
Summary: After 5 years of dating, Jeff decides he wants to propose Annie. He has the ring, he has a plan. Simple, right? Well it wouldn’t be Greendale if everything actually went right the first time... or second... or third...
A/N: This is the first fanfiction I wrote that I am actually proud of enough to post online. Hope you guys like it. :)
1. Restaurant
“So tomorrow’s your anniversary?” Abed asked emotionlessly.
“Yep,” Jeff responded as he took a pull from his beer.
“Have anything planned?”
“Yep.” Jeff smiled as he turned to face his friend. “I’m going to propose.”
“Nice. How are you going to do it?”
“I made reservations at the fancy Italian place we went to on our first official date.”
“Hmm…”
“What ‘hmm’? I’m going to take her out to a great restaurant, which I know she loves, and in between dinner and dessert I’m going to surprise her with the ring.”
“It’s a cliché.”
“I think you mean classic.”
“Nope, cliché. Just watch, it’ll fail.”
“Shut up, Abed.”
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What the hell did Abed know anyways? Annie loved this place, and when she saw the ring, she’d be so excited she wouldn’t even think to call his mode of proposal a cliché. Well, she did spend a lot of time with Abed, so it would probably come up at some point, but by then it wouldn’t matter.
“I still can’t believe you remembered this place,” Annie commented after their waiter left.
“Like I could forget. You talked about the tiramisu for a week after our first date.” Jeff took a hold of Annie’s hand. “And since it is our five year anniversary, I wanted to take you somewhere I knew you’d…”
“Jeff? Annie?” an annoyingly familiar voice interrupted.
“Rich?!” Annie cheerfully exclaimed as she leaped up to greet the interloper. “It’s so great to see you!”
“…love,” Jeff finished even though no one was paying attention to him. They were, however, hugging now. Great.
“It’s so great to see you, too, Annie! And you as well, Jeff!” Rich said gleefully, oblivious to the moment he had just ruined.
“Rich,” Jeff muttered, “What exactly are you doing here? Now? In this restaurant? On this night?”
“Jeff!” Annie scolded.
“No, no, it’s okay, Annie. I was supposed to meet a date here but she had to cancel at the last minute because of a work emergency.”
“Aww, how disappointing. Well, hope you enjoy the rest of your evening,” Jeff said, hoping to get him away.
“Or you could join us,” Annie offered. Jeff’s eyes darted to hers, hoping to find some way to silently change her mind, but he could tell it was already too late.
“That sounds great! I’d love to catch up with you guys,” Rich beamed. “Only if it’s okay with you, Jeff.”
“It’s fine with him,” Annie answered, putting the final nail in the coffin of that evening.
“Is it, Jeff?” Rich asked to confirm.
“Yeah, yeah, whatever,” Jeff said unenthusiastically.
“Great!” Rich smiled as he pulled a chair over from the other table and flagged over a waiter.
Well, this evening was going to suck.
2. Home
“So how did your proposal go?”
“It didn’t.”
“I told you it was too cliché.”
“Rich had a date at the restaurant who bailed at the last minute and Annie decided to invite him to join us.”
“I could’ve told you that would happen.”
“Well, you didn’t.”
“It’s what happened on Friends when Chandler tried to propose to Monica.”
“What did Chandler do after that?”
“He tried to convince Monica that he would never propose to her while he thought of a new idea.”
“That sounds stupid.”
“It was, he almost lost her.”
“Well I’m not going to do that. Especially since I already have another plan.”
“What this time?”
“I’m going to cook her favorite dinner, light a few candles - make the apartment a ‘den of romance’ -- and this time if Rich tries to cut in, I can tell him to fuck off.”
“Nice.”
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Jeff refused to acknowledge that Abed was right about his first proposal attempt failing because it was a cliché. It was a coincidence, a freak bizarre accident, or maybe some kind of cosmic punishment or test to see if he was truly committed to Annie. Well, he was, so take that, universe! His new plan was practically flawless - setting up for it gave him a good excuse to leave work early and most important of all, there was no way Rich could interfere this time.
He was just setting up the final details when the time of Annie’s usual arrival approached. Any minute now he would hear her keys in the door and see her surprised face at what he’d done.
At 6:30, Jeff lit the last candle and got into position in front of the door.
Five minutes later, nothing happened.
Ten minutes later, still nothing happened.
Fifteen minutes later, Jeff blew the candles out and moved to sit on the couch.
It wasn’t until twenty minutes after he first got into position that the phone rang and Jeff figured that Annie was stuck in traffic. She wasn’t. Apparently there was some emergency at the hospital so Annie had to stay late but she’d get home as soon as she could and would call first if it wasn’t too late.
By 8 PM, Jeff had put everything away and started looking over the files for the case he had to present in court on Monday.
By 10 PM he had given up any hope of salvaging the evening, deciding to change to a pair of sweats and lounge on the couch.
When Annie finally got home at midnight she found him passed out on the couch with the TV on and a can of whipped cream in his hand.
3. Thanksgiving
“How was your dinner?”
“What dinner?”
“The one where you were going to propose?”
“Oh yeah. Didn’t happen.”
“Rich again?”
“No, there was some emergency at the hospital so she had to work late.”
“I see.”
“You haven’t been telling people about my plan, right?”
“Right.”
“Good.”
“Why?”
“Because I actually want it to be a surprise. And because my only idea at the moment involves Thanksgiving.”
“Cliché”
“It is not, cliché! How many times have you seen someone propose during Thanksgiving dinner?”
“Not many, but…”
“Ah hah!”
“Are you going to hide the ring in her dessert?”
“Yes.”
“There’s the cliché.”
“Abed?”
“Yes, Jeff?”
“Shut up.”
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Yes, Jeff knew that putting the ring in a dessert was a cliché, but at this point, he was going for broke and maybe using such an over the top approach would finally be enough to get the damn proposal out.
What Jeff didn’t realize was how difficult getting the ring in her pie would be at Shirley’s house, even with Abed’s help. Apparently when Jeff and Abed volunteered to serve dessert, Shirley thought they were going to recreate American Pie with her prized baking. At least that’s the only way Jeff could explain her coming into the kitchen every three minutes to check up on them, delaying the whole process.
When she came in the fourth time, Jeff silently pressed the ring into Abed’s palm behind the counter before walking up to distract Shirley, using his large stature to block her view of the younger man.
“I just want to make sure everything is okay,” Shirley whined.
“We have everything covered here, you have nothing to worry about,” Jeff assured her.
“Jeffrey, if you blow up my kitchen, I swear…”
“Shirley, we’re just cutting the pie and putting it on plates. We aren’t using anything that could blow up your kitchen,” Jeff interrupted with his ever-present smirk .
“Careful, boy!” Shirley warned. Before she could say anything Abed came over with a few of the plates.
“They’re all ready,” he said as he went into the dining room.
“See, everything’s okay,” Jeff snarked. Shirley just gave him a dirty look and muttered something incomprehensible as she went over to grab a few plates.
It was only after she left the kitchen that Jeff realized he didn’t know which plate Abed put the ring in, or if it was even still on the table. Trying not to panic, Jeff scanned the remaining dishes and saw one where the whipped cream looked like it had been rearranged. He grabbed the remaining few plates and walked out into the living room.
“Milady,” he said sweetly as he placed the special plate in front of Annie, leaning down to give her a quick kiss on the cheek.
“Thank you, Milord,” she replied with a smile.
“Annie, I just wanted to tell you again how much you mean to me. I’ve been happier these last five years with you than I’ve ever been before and…”
Troy started coughing.
“Oh my God, I think he’s choking!” Annie exclaimed, her eyes wide.
“I’m sure he’ll be okay,” Jeff replied- and he was, but the Heimlich maneuver Abed was using on Troy resulted in something shiny falling into his hand. Before he had the chance to comment on it, Jeff ran over to Troy and pulled him into the kitchen, with Abed trailing not too far behind.
“Why was there a ring in my pie?!” Troy asked as soon as Jeff took his hand off the younger man’s mouth “Was there supposed to be a prize?”
“Yeah, just not for you,” Jeff growled, thrusting the glass he had just obtained in front of Troy.
“Why not for me?!” Troy whined “Am I not good enough for your prize?!”
“Jeff was planning to propose to Annie,” Abed said blankly.
“He was?! You were?!” Troy asked gleefully. Jeff merely nodded in response. “And you did it by hiding her ring in pie? That’s pretty cliché, man.”
“Told you,” Abed commented, pointing a finger at Jeff.
“Well if someone had made clear which piece they hid the ring in, this wouldn’t have happened.”
“I had to rearrange the whipped cream on all of the pieces, otherwise it would’ve looked obvious that there was something different about one of the pieces.”
“So if you knew which piece was supposed to go to Annie, why couldn’t you just give that one to her?”
“I did. She must have switched it when I wasn’t looking.”
“Actually,” Troy interjected sheepishly, “she passed it on.”
4. Skywriter
“So a little birdie tells me you’re thinking of proposing to Annie,” Britta said smugly as Jeff grabbed another beer.
“Troy!” he growled, “I know she’s your girlfriend, but that doesn’t mean you have to tell her everything!”
“You almost killed my boyfriend, you douche! I think I’m entitled to know why.”
“Okay, first off, it’s unlikely that he would have actually died. Second off, I didn’t want you knowing because I didn’t want you to Britta it.”
“How could I possibly ruin this?!”
“By telling her before I got the chance to do it.”
“I can keep a secret! Besides, I can help you come up with proposal ideas.”
Jeff looked at her skeptically.
“Do you actually have a new idea?”
Jeff stared her down for a bit before shaking his head and sighing. “What’s your idea?”
“Some big romantic gesture. Girls like Annie go gaga over that shit.”
“Thanks, Sherlock. Any other suggestion?”
“I wasn’t done, jerk!”
“Fine, what’s the rest?”
“Get a skywriter outside the hospital during her lunch break.”
“A skywriter?”
“Yeah, she’ll melt in a puddle of Annie goo and you’ll have yourself a fiancé.”
“You better be right about this, Perry.”
“I will be, Winger.”
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The very fact that Jeff even took Britta’s suggestion seriously should indicate just how desperate he was. He questioned the decision at least ten times before finally forcing himself to just place the order for the next day.
Placing the order did nothing to relieve the anxiety building within him. In fact, every passing hour seemed to bring more things for him to worry about.
What if there was a freak storm?
What if she decided not to go to work the next day?
What if he didn’t get her out of the building in time?
What if she somehow found out?
What if Britta was wrong and Annie didn’t actually like skywriters?
What if Britta had told Annie already?
Jeff spent half the night staring at the clock on the cable box, listening to Annie’s even breath as she slept beside him. He really just wanted to get the proposal out already. The beautiful ring was now burning a hole in his pocket and he was growing increasingly paranoid that Annie would accidentally find it before he got a chance to propose. What if his inability to propose was a sign from the universe that he wasn’t meant to get married? What if it meant that he wasn’t supposed to be with Annie? If it had been any other woman, Jeff would have given up after the first failed attempt - any more time would not have been worth the effort. But as he looked down at his sleeping girlfriend, he knew that this was absolutely worth it. He would come up with a hundred more proposals if he had to.
Jeff finally fell asleep at 3 AM when Annie rolled over in her sleep, putting her head on his chest and her arm on his stomach as if she somehow knew he needed her.
Despite only getting a few hours of sleep, Jeff felt energized from the moment he woke up. Thankfully, he didn’t have to court that day. He went into the firm to finish up some last minute paperwork on a settlement, then took an extremely early lunch in order to make it to Greendale Memorial in order to get Annie out early enough to see his proposal. He had already confirmed with the company he hired that they would be there when they were supposed to be. Everything was set in motion; he just needed to get Annie.
“Hello, Patrice.” Jeff greeted Annie’s co-worker with a charming smile as he walked over to her desk.
“Jeffrey,” she greeted in return. “Are you here to pick Annie up for a surprise lunch date?”
“I most certainly am, is she around?”
“I’ll check now.” Patrice picked up the phone to call Annie’s boss. As long as Annie wasn’t in the psych ward, Jeff was pretty sure he could charm anyone into letting her go.
“Alright, thank you,” Patrice said into the receiver before hanging up and turning to Jeff. “I’m afraid she’s up at the psych ward, but as soon as she can get Mr. Lowenstein to take his medicine she’ll come down.”
Well damn. Mr. Lowenstein was an elderly man who, for whatever reason, had developed a bond with Annie and refused to trust any of the nurses at the hospital. Even though Annie wasn’t a nurse, she would frequently have to help them administer his medicine, a procedure that took anywhere between ten minutes and two hours depending on how convinced he was that the staff had poisoned his medication.
“Do you know how long she was up there for?” Jeff asked desperately.
“No, but her supervisor said she should be done any minute now.”
‘Any minute now’ turned out to be half an hour later. At that point, Jeff knew he wasn’t going to be able to salvage the proposal so he stayed long enough to give Annie the flowers he picked up on his way over and give her a quick kiss.
5. Holiday Party
“So Jeffrey, do you have any news you would like to share with me?” Shirley asked sweetly during their monthly lunch date at Senior Kevin’s.
“I got my Christmas bonus early and it’s bigger than I expected?” Jeff offered weakly.
“Boy, you know that’s not what I’m talking about!”
“What are you talking about?” Jeff really didn’t like where this was going.
“Britta told me you were planning on proposing to Annie!” Shirley practically announced.
“Geez, Shirley, say it a little louder, I don’t think the people all the way at the back heard you!”
“Don’t you use that tone with me, boy,” Shirley warned.
“Sorry, I’m just trying to keep it a secret. When did Britta tell you anyways?”
“Last Friday.” Great, so when Britta said she could keep a secret, clearly that meant she could stay quiet for three days. She was going to make a terrible therapist. At least she didn’t tell Annie...
“Annie doesn’t know, right?!” Jeff’s brain went into hyper-drive. If Annie knew that would take out the element of surprise and...
“Oh, relax, no one told her.”
“Shirley,” Jeff grabbed her hands “I need you to appreciate just how important it is that Annie doesn’t find out about this before I get a chance to propose.”
“Don’t worry, I won’t tell her.”
“Really? Thank you.” Jeff released her hands, letting out the breath he hadn’t realized he was holding in.
“You’re welcome. Now, did you think of a new way to propose?”
“Not yet. Have any suggestions for me?”
“You should do it at her office holiday party.”
“A holiday party? Really?”
“Yes, just think about it: you’ll both already be dressed up, there will be decorations up, it’ll be perfect.”
“You make a good point but why does it have to be at her holiday party? We’re going to the party at my office tomorrow night and hers isn’t until next week.”
“Because I helped her plan out which dress she’s going to wear and the one she’s wearing to her party is better.”
“What if she changes her mind?”
“I thought we were talking about Annie Edison...” Shirley deadpanned. She had a point, Annie had a tendency to plan outfits out weeks ahead of time, so it wouldn’t be surprising. Especially to a special event like a party.
“Besides, do you really want to propose in front of your colleagues? Are any of them still married to their first wives?” Though Jeff was tempted to point out that most of the married men working at his firm were still with their first wives, but he did agree that Annie shouldn’t surrounded by lawyers only seconds after she got engaged. At least she had some friends at the hospital.
“Alright,” Jeff sighed “I’ll propose at her holiday party.
“That’s nice!” Shirley cheered. “And if she just happens to associate a positive moment in her life with Jesus, then that’s just a happy coincidence.”
“Shirley!”
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“Alright, I’m ready!” Annie called out from their bedroom.
Finally! Jeff had been waiting over an hour for her to finish dressing and primping. Quite impatiently. Ever since Shirley let it slip about Annie’s dress, Jeff had been counting down the days until he could see it.
“Well, what do you think?” Annie asked when she came out into the living room and twirled around, allowing Jeff to get a full look at her dress.
“Wow...” was all he could say. She was wearing a strapless red dress with a satin belt and small embroidered snowflakes. Her hair cascaded down her shoulders in waves and the only pieces of jewelry she was wearing were a gold barrette to keep her hair to the side and a thin gold bracelet.
“I take it you mean that to be a good wow?” Annie asked as she wrapped a gold satin shrug around her shoulders.
“Of course it’s a good wow,” Jeff answered with a charming smile. Shirley was right when she told him to hold off. Not that there was anything wrong with the dress she wore to his office holiday party - a more conservative black dress - it just wasn’t as appropriate for what he was planning on doing. This dress, however, was the perfect dress for a proposal.
“I even got you a present,” Annie said as she presented a small black box from one of the drawers of her desk. “In case you wanted to match.”
“Annie...” Jeff found himself speechless as he looked down at the red satin tie that matched the belt on her dress.
“Here, let me.” She gently pulled his hands apart to stand close enough to be able to remove the tie he was wearing. Jeff couldn’t suppress a hard swallow when Annie’s hand brushed his neck. As Annie worked to put on the new tie, Jeff had to use all of his strength to keep from proposing on the spot and getting to the other thing he had planned for the evening. As much as he loved seeing Annie in that dress, he really couldn’t wait to see her without it.
“I know how much you hate going to these things,” Annie said as she tugged on the knot to secure it, “but it will be over before you know it and as soon as we get home, I’ll make it up to you.”
“That sounds suspiciously similar to the pep talk I gave you before my office’s holiday party.”
“What can I say? I learned from the best.”
When they got to the hospital cafeteria Jeff was even surer that this was the perfect place to propose. Red and green streamers were carefully hung around the room and small LED lights looked like twinkling stars. If there was ever a perfect place to propose - this was it. As Annie made her rounds around the room to greet her fellow coworkers, Jeff went over to the bar.
“Is that your girlfriend?” asked the man who was leaning against the bar when Jeff ordered.
“Yeah.” Jeff couldn’t suppress a proud smile.
“That’s mine.” The man pointed to a taller woman in a blue dress who was animatedly discussing something with Annie. “I’m Greg,” the man added as he offered his hand.
Jeff reached forward to shake it. “Jeff.”
“Nice to meet you, Jeff.” Greg paused to take a drink. “So, how long have you two been together?”
“Annie and I have been together for five years now.”
“Ah.”
“How about you and...” Jeff was sure he knew the name of the woman; he just couldn’t remember it at the moment. It was definitely something that began with an ‘m’. Molly? Mary?
“Maggie,” Greg filled in. “We’ve been together for two years tonight.”
“Hell of a way to spend your anniversary.”
“I know.”
“Here you go,” the bartender interrupted to give Jeff his drinks.
“Well, Greg, it was nice meeting you.”
“It was nice meeting you too, Jeff.” Greg and Jeff shook hands again before Jeff took the drinks and went towards where Annie was standing.
“And then he got us reservations at this beautiful restaurant at the Eiffel Tower. Oh, it was so great! Have you ever been to the Eiffel Tower? You should go, it’s so amazing!” Jeff heard Maggie chirp. The closer he got to the pair, the clearer it was to Jeff that the conversation was very much one-sided.
“That sounds like quite a trip,” Jeff chimed in as Maggie stopped to take a sip of her wine.
“Jeff!” Annie practically cheered.
“Milday,” Jeff gave Annie the appletini he got her. Once Annie took the drink, Jeff took hold of her free hand, ready to extricate her.
“Oh my God! You’re Jeff?! Annie told me so much about you! She’s right, you are handsome! If I wasn’t so happy with my millionaire, I would steal you right up!”
“Speaking of steal, if you don’t mind, I’m going to steal my girlfriend back.” Jeff didn’t wait for Maggie to respond as he pulled Annie away.
“Thank you!” Annie said when they were out of earshot. “I thought she was never going to stop talking!”
Jeff put his arm around Annie, pulling her close.
“She just went on and on about her boyfriend.” Annie’s voice was muffled by Jeff’s body.
“Apparently he’s a millionaire.”
“I doubt he actually has a million dollars but he’s an investment banker so I’m sure money isn’t an issue for them.”
“Hearing also doesn’t seem to be an issue.” Annie lifted her head from Jeff’s chest to shoot him a confused look. “I met him at the bar.”
“Ah,” she nodded and looked around to see that Maggie had already latched onto some other poor soul.
“Want to grab some dinner before she makes her way over to the buffet table and clogs the line?” Jeff asked softly in Annie’s ear.
“Yes!”
The pair spent the next hour eating, having short conversations with some of Annie’s other co-workers, and dancing. Jeff was enjoying himself so much that he nearly forgot about the proposal. As they were dancing to a slow song, the last before the band was set to have a short break, Jeff decided he would propose as soon as the song ended. When it did end, Annie took a step back to look up at him and flash him a smile so full of love that it took his breath away. This was it. This was the perfect moment. The one he had been trying so hard to create for a month and a half. All that was left to do was to finally pop the question.
“Annie...” he started, suddenly nervous. Annie, on her part, continued to smile at him as if he was the most amazing man in the world. He could do this. He was going to do this.
“Maggie?” A familiar voice rang out. Jeff tore his gaze away from Annie to see Greg standing near the bandstand with a microphone.
“Maggie Thompson?” Greg asked again as he walked towards Maggie who was standing only a few feet away from Jeff and Annie, her hands covering her mouth, in stunned silence, probably the first time in her life.
“Maggie Thompson, for the last two years you have made me the happiest man in the world. You’re beautiful, smart, funny, and you have the voice of an angel. Will you please do me the honor--” Greg got down on one knee, producing a ring from his pocket “--of being my wife?”
“Yes!” Maggie screeched. “Oh my God! Yes!”
Well, Jeff’s thunder was effectively stolen. There was just no way he could come back from this. And here he thought he was on good terms with Greg! Looking over at Annie, Jeff could just tell she was disappointed. Even though she was smiling and genuinely happy for her co-worker, because that’s just the kind of person that Annie was, Jeff could tell that deep down she was disappointed.
The whole marriage issue had been a sore point in their relationship from almost the beginning. The fact that a co-worker, whom Annie wasn’t too fond of, had gotten engaged after only two years while Annie and Jeff had been together for five years only made the situation that much worse. In fact, Jeff was actually starting to worry that Annie would break up with him before he even got a chance to propose.
“Hey.” Jeff pulled Annie close to him, placing a soft kiss on the top of her head. “Let’s just go home.”
“In a minute,” Annie responded without looking up at him. “I want to go offer my best wishes to Maggie.”
It took Annie twenty minutes just to get to Maggie and another ten before Annie was able to leave. Jeff wasn’t standing directly next to them, but he was sure he heard Maggie say something along the lines of “don’t worry, he’ll propose someday.” Great, as if it wasn’t enough to ruin his plan, she had to rub the fact that she’s engaged in Annie’s face, too.
Annie was silent on the car ride home, just staring outside the window. Her mood didn’t seem to improve much when they got home. They had slept together, but after five years, Jeff could tell when he was getting pity sex. As soon as they finished, Annie turned to her side facing away from him.
“I’ll make it up to you, Annie,” he whispered as he looked down at her sleeping form. “I promise, I’ll make it better.”
And he would make it better. He’d figure out the perfect new proposal plan, and fast. He just had to. There was no way he could lose Annie.
6. Birthday
Jeff finally had it - the perfect proposal, almost guaranteed to be foolproof. As long as Annie stayed with him for the one week between the hospital holiday party and her birthday, he just knew he could get his plan to work. He even made sure to be the perfect most attentive boyfriend ever. This was phase one of his plan.
Phase two was to have Britta, Abed and Shirley be on the lookout for any signs that Annie was having doubts about the relationship and to let him know as soon as they found out without letting it slip that he was planning to propose.
Phase three was to make sure that no one from Annie’s workplace called her in on her birthday. Annie’s birthday fell on one of her days off but there was still a chance she could be called in and Jeff had to make sure that didn’t happen.
So far everything seemed to be going well. The first few nights after the holiday party, Annie came home later than usual. Jeff wasn’t sure if it was because she was stuck in conversations with Maggie, who was undoubtedly in full-on wedding planning mode, or because she didn’t want to see him. He really hoped it was the former, was almost sure of it, but he couldn’t rule out that it was the latter or maybe even a combination of the two. In any case, Jeff made sure he was home early every day that week in order to make Annie her favorite meals for dinner. He even bribed Patrice to call him as soon as Annie left so he didn’t have a repeat of his second proposal attempt. Thankfully, Annie had gone straight home every day.
The last time the proposal issue had come up she went out with Britta or one of her co-workers every night just so she could avoid spending any time with him. But considering that any time the two were together they could argue, it made sense as to why she wanted to stay away from him. One night it got so bad that she spent the night at Britta’s place. This time was different, thankfully. After the third night of coming home to dinner and a massage, everything went back to normal- for the most part. Jeff could tell Annie wanted to talk about the marriage issue but she clearly didn’t want to get in a fight before her birthday. Still, every day he could see her desire to bring it up. Every day he prayed that she would wait and every day he got more and more nervous.
Now that it was the morning of her birthday, Jeff felt like he was finally in the homestretch. Annie usually woke up at 9 AM on her days off, so Jeff made sure he was awake with enough time to make her favorite breakfast - cinnamon pancakes with whipped cream and sliced strawberries. He turned off their cell phones and the alarm clock, even going the extra step to unplug the landline. Nothing was going to wake Annie up before he was ready.
Double-checking the tray he set up for the occasion, Jeff took a deep breath and went to their bedroom to see that Annie was still asleep. Setting the tray on the dresser so nothing accidentally knocked over, Jeff walked over to the bed and placed a soft kiss on Annie’s forehead. Though her eyes remained closed, Annie’s lips curled up into a smile.
“Wake up, Annie,” Jeff whispered as he placed soft kisses around her face. He didn’t stop until one of her eyes opened.
“Happy Birthday, Milady,” Jeff said before getting up to bring over the tray.
“Mmm, this is the best way to wake up.” Annie smiled as she dug into her food.
“Nothing but the best for the best girlfriend in the world.”
“You’re just saying that because it’s my birthday and you want to be on my good side,” Annie pointed her strawberry-topped fork at Jeff. “But I’ll accept it.”
Jeff merely chuckled in response, experiencing the same flash of absolute certainty he had before his failed proposal at the hospital. If Annie’s reaction to the birthday breakfast was a preview of what married life would be like then Jeff couldn’t wait to finally be able to call her his wife. And it’s not like Jeff was suddenly naïve, he spent enough time around divorce lawyers to know that always doesn’t last, well, always. But with Annie, it was different. Not only was he willing to take the risk with her, he was actually excited to do so.
“Thank you so much for the breakfast in bed,” Annie smiled.
“I’m glad you liked it,” Jeff smiled back. “I hope you like the other things I have planned for today.”
“Jeff Winger planned things? I’m intrigued,” she teased. “What are we doing first?”
“First, I need to ask you something.”
“Ask away.”
“Alright,” Jeff exhaled, suddenly nervous that Annie would say no.
“Annie, these last five years with you have been the best five years of my life. I never thought I could ever love anyone as much as I love you, never thought I was even capable of being in a long-term relationship until I met you, but you have made me realize that I am capable of more than I ever thought I was. I know the timing may be suspicious, but please trust me when I say that I have been trying to ask you this since our anniversary.” Sliding off the bed to get down on one knee, Jeff pulled the ring box out of the pocket of his sweat pants. “Annie Edison, will you please marry me?”
Annie’s eyes went wide as she saw the ring, a four-carat princess cut diamond, beautiful without being too flashy. It had taken him two weeks just to find the ring, but once he saw it, he had known it was the perfect one and bought it on the spot.
“Are you serious?” Annie asked in wide-eyed shock.
“As serious as I’ve ever been about anything in my life.” Jeff tried to keep his voice steady but he knew he wasn’t faring too well. This was it. He had waited too long and now she was going to say no and leave him forever.
“Yes.”
“I’m sorry, could you please say that again?” Jeff was convinced he heard her wrong.
“Yes!” Annie repeated, reaching for the ring box. “My answer is yes!”
Jeff practically leaped forward to kiss her. After two and a half months and five failed proposals, he finally heard the sweetest word in the English language: “Yes”.
Author: edenofalltrades
Pairing:Jeff/Annie
Spoilers: I wrote the story before season 4 started airing but I edited it after that so there are some very minor spoilers from the first few episodes of season 4.
Rating/Warnings: Teen/PG-13. It’s fairly mild but there is minor course language, including one f-bomb.
Word Count: 5,772
Disclaimers: I do not own Community and will not be making any profit from this story
Summary: After 5 years of dating, Jeff decides he wants to propose Annie. He has the ring, he has a plan. Simple, right? Well it wouldn’t be Greendale if everything actually went right the first time... or second... or third...
A/N: This is the first fanfiction I wrote that I am actually proud of enough to post online. Hope you guys like it. :)
1. Restaurant
“So tomorrow’s your anniversary?” Abed asked emotionlessly.
“Yep,” Jeff responded as he took a pull from his beer.
“Have anything planned?”
“Yep.” Jeff smiled as he turned to face his friend. “I’m going to propose.”
“Nice. How are you going to do it?”
“I made reservations at the fancy Italian place we went to on our first official date.”
“Hmm…”
“What ‘hmm’? I’m going to take her out to a great restaurant, which I know she loves, and in between dinner and dessert I’m going to surprise her with the ring.”
“It’s a cliché.”
“I think you mean classic.”
“Nope, cliché. Just watch, it’ll fail.”
“Shut up, Abed.”
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What the hell did Abed know anyways? Annie loved this place, and when she saw the ring, she’d be so excited she wouldn’t even think to call his mode of proposal a cliché. Well, she did spend a lot of time with Abed, so it would probably come up at some point, but by then it wouldn’t matter.
“I still can’t believe you remembered this place,” Annie commented after their waiter left.
“Like I could forget. You talked about the tiramisu for a week after our first date.” Jeff took a hold of Annie’s hand. “And since it is our five year anniversary, I wanted to take you somewhere I knew you’d…”
“Jeff? Annie?” an annoyingly familiar voice interrupted.
“Rich?!” Annie cheerfully exclaimed as she leaped up to greet the interloper. “It’s so great to see you!”
“…love,” Jeff finished even though no one was paying attention to him. They were, however, hugging now. Great.
“It’s so great to see you, too, Annie! And you as well, Jeff!” Rich said gleefully, oblivious to the moment he had just ruined.
“Rich,” Jeff muttered, “What exactly are you doing here? Now? In this restaurant? On this night?”
“Jeff!” Annie scolded.
“No, no, it’s okay, Annie. I was supposed to meet a date here but she had to cancel at the last minute because of a work emergency.”
“Aww, how disappointing. Well, hope you enjoy the rest of your evening,” Jeff said, hoping to get him away.
“Or you could join us,” Annie offered. Jeff’s eyes darted to hers, hoping to find some way to silently change her mind, but he could tell it was already too late.
“That sounds great! I’d love to catch up with you guys,” Rich beamed. “Only if it’s okay with you, Jeff.”
“It’s fine with him,” Annie answered, putting the final nail in the coffin of that evening.
“Is it, Jeff?” Rich asked to confirm.
“Yeah, yeah, whatever,” Jeff said unenthusiastically.
“Great!” Rich smiled as he pulled a chair over from the other table and flagged over a waiter.
Well, this evening was going to suck.
2. Home
“So how did your proposal go?”
“It didn’t.”
“I told you it was too cliché.”
“Rich had a date at the restaurant who bailed at the last minute and Annie decided to invite him to join us.”
“I could’ve told you that would happen.”
“Well, you didn’t.”
“It’s what happened on Friends when Chandler tried to propose to Monica.”
“What did Chandler do after that?”
“He tried to convince Monica that he would never propose to her while he thought of a new idea.”
“That sounds stupid.”
“It was, he almost lost her.”
“Well I’m not going to do that. Especially since I already have another plan.”
“What this time?”
“I’m going to cook her favorite dinner, light a few candles - make the apartment a ‘den of romance’ -- and this time if Rich tries to cut in, I can tell him to fuck off.”
“Nice.”
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Jeff refused to acknowledge that Abed was right about his first proposal attempt failing because it was a cliché. It was a coincidence, a freak bizarre accident, or maybe some kind of cosmic punishment or test to see if he was truly committed to Annie. Well, he was, so take that, universe! His new plan was practically flawless - setting up for it gave him a good excuse to leave work early and most important of all, there was no way Rich could interfere this time.
He was just setting up the final details when the time of Annie’s usual arrival approached. Any minute now he would hear her keys in the door and see her surprised face at what he’d done.
At 6:30, Jeff lit the last candle and got into position in front of the door.
Five minutes later, nothing happened.
Ten minutes later, still nothing happened.
Fifteen minutes later, Jeff blew the candles out and moved to sit on the couch.
It wasn’t until twenty minutes after he first got into position that the phone rang and Jeff figured that Annie was stuck in traffic. She wasn’t. Apparently there was some emergency at the hospital so Annie had to stay late but she’d get home as soon as she could and would call first if it wasn’t too late.
By 8 PM, Jeff had put everything away and started looking over the files for the case he had to present in court on Monday.
By 10 PM he had given up any hope of salvaging the evening, deciding to change to a pair of sweats and lounge on the couch.
When Annie finally got home at midnight she found him passed out on the couch with the TV on and a can of whipped cream in his hand.
3. Thanksgiving
“How was your dinner?”
“What dinner?”
“The one where you were going to propose?”
“Oh yeah. Didn’t happen.”
“Rich again?”
“No, there was some emergency at the hospital so she had to work late.”
“I see.”
“You haven’t been telling people about my plan, right?”
“Right.”
“Good.”
“Why?”
“Because I actually want it to be a surprise. And because my only idea at the moment involves Thanksgiving.”
“Cliché”
“It is not, cliché! How many times have you seen someone propose during Thanksgiving dinner?”
“Not many, but…”
“Ah hah!”
“Are you going to hide the ring in her dessert?”
“Yes.”
“There’s the cliché.”
“Abed?”
“Yes, Jeff?”
“Shut up.”
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Yes, Jeff knew that putting the ring in a dessert was a cliché, but at this point, he was going for broke and maybe using such an over the top approach would finally be enough to get the damn proposal out.
What Jeff didn’t realize was how difficult getting the ring in her pie would be at Shirley’s house, even with Abed’s help. Apparently when Jeff and Abed volunteered to serve dessert, Shirley thought they were going to recreate American Pie with her prized baking. At least that’s the only way Jeff could explain her coming into the kitchen every three minutes to check up on them, delaying the whole process.
When she came in the fourth time, Jeff silently pressed the ring into Abed’s palm behind the counter before walking up to distract Shirley, using his large stature to block her view of the younger man.
“I just want to make sure everything is okay,” Shirley whined.
“We have everything covered here, you have nothing to worry about,” Jeff assured her.
“Jeffrey, if you blow up my kitchen, I swear…”
“Shirley, we’re just cutting the pie and putting it on plates. We aren’t using anything that could blow up your kitchen,” Jeff interrupted with his ever-present smirk .
“Careful, boy!” Shirley warned. Before she could say anything Abed came over with a few of the plates.
“They’re all ready,” he said as he went into the dining room.
“See, everything’s okay,” Jeff snarked. Shirley just gave him a dirty look and muttered something incomprehensible as she went over to grab a few plates.
It was only after she left the kitchen that Jeff realized he didn’t know which plate Abed put the ring in, or if it was even still on the table. Trying not to panic, Jeff scanned the remaining dishes and saw one where the whipped cream looked like it had been rearranged. He grabbed the remaining few plates and walked out into the living room.
“Milady,” he said sweetly as he placed the special plate in front of Annie, leaning down to give her a quick kiss on the cheek.
“Thank you, Milord,” she replied with a smile.
“Annie, I just wanted to tell you again how much you mean to me. I’ve been happier these last five years with you than I’ve ever been before and…”
Troy started coughing.
“Oh my God, I think he’s choking!” Annie exclaimed, her eyes wide.
“I’m sure he’ll be okay,” Jeff replied- and he was, but the Heimlich maneuver Abed was using on Troy resulted in something shiny falling into his hand. Before he had the chance to comment on it, Jeff ran over to Troy and pulled him into the kitchen, with Abed trailing not too far behind.
“Why was there a ring in my pie?!” Troy asked as soon as Jeff took his hand off the younger man’s mouth “Was there supposed to be a prize?”
“Yeah, just not for you,” Jeff growled, thrusting the glass he had just obtained in front of Troy.
“Why not for me?!” Troy whined “Am I not good enough for your prize?!”
“Jeff was planning to propose to Annie,” Abed said blankly.
“He was?! You were?!” Troy asked gleefully. Jeff merely nodded in response. “And you did it by hiding her ring in pie? That’s pretty cliché, man.”
“Told you,” Abed commented, pointing a finger at Jeff.
“Well if someone had made clear which piece they hid the ring in, this wouldn’t have happened.”
“I had to rearrange the whipped cream on all of the pieces, otherwise it would’ve looked obvious that there was something different about one of the pieces.”
“So if you knew which piece was supposed to go to Annie, why couldn’t you just give that one to her?”
“I did. She must have switched it when I wasn’t looking.”
“Actually,” Troy interjected sheepishly, “she passed it on.”
4. Skywriter
“So a little birdie tells me you’re thinking of proposing to Annie,” Britta said smugly as Jeff grabbed another beer.
“Troy!” he growled, “I know she’s your girlfriend, but that doesn’t mean you have to tell her everything!”
“You almost killed my boyfriend, you douche! I think I’m entitled to know why.”
“Okay, first off, it’s unlikely that he would have actually died. Second off, I didn’t want you knowing because I didn’t want you to Britta it.”
“How could I possibly ruin this?!”
“By telling her before I got the chance to do it.”
“I can keep a secret! Besides, I can help you come up with proposal ideas.”
Jeff looked at her skeptically.
“Do you actually have a new idea?”
Jeff stared her down for a bit before shaking his head and sighing. “What’s your idea?”
“Some big romantic gesture. Girls like Annie go gaga over that shit.”
“Thanks, Sherlock. Any other suggestion?”
“I wasn’t done, jerk!”
“Fine, what’s the rest?”
“Get a skywriter outside the hospital during her lunch break.”
“A skywriter?”
“Yeah, she’ll melt in a puddle of Annie goo and you’ll have yourself a fiancé.”
“You better be right about this, Perry.”
“I will be, Winger.”
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The very fact that Jeff even took Britta’s suggestion seriously should indicate just how desperate he was. He questioned the decision at least ten times before finally forcing himself to just place the order for the next day.
Placing the order did nothing to relieve the anxiety building within him. In fact, every passing hour seemed to bring more things for him to worry about.
What if there was a freak storm?
What if she decided not to go to work the next day?
What if he didn’t get her out of the building in time?
What if she somehow found out?
What if Britta was wrong and Annie didn’t actually like skywriters?
What if Britta had told Annie already?
Jeff spent half the night staring at the clock on the cable box, listening to Annie’s even breath as she slept beside him. He really just wanted to get the proposal out already. The beautiful ring was now burning a hole in his pocket and he was growing increasingly paranoid that Annie would accidentally find it before he got a chance to propose. What if his inability to propose was a sign from the universe that he wasn’t meant to get married? What if it meant that he wasn’t supposed to be with Annie? If it had been any other woman, Jeff would have given up after the first failed attempt - any more time would not have been worth the effort. But as he looked down at his sleeping girlfriend, he knew that this was absolutely worth it. He would come up with a hundred more proposals if he had to.
Jeff finally fell asleep at 3 AM when Annie rolled over in her sleep, putting her head on his chest and her arm on his stomach as if she somehow knew he needed her.
Despite only getting a few hours of sleep, Jeff felt energized from the moment he woke up. Thankfully, he didn’t have to court that day. He went into the firm to finish up some last minute paperwork on a settlement, then took an extremely early lunch in order to make it to Greendale Memorial in order to get Annie out early enough to see his proposal. He had already confirmed with the company he hired that they would be there when they were supposed to be. Everything was set in motion; he just needed to get Annie.
“Hello, Patrice.” Jeff greeted Annie’s co-worker with a charming smile as he walked over to her desk.
“Jeffrey,” she greeted in return. “Are you here to pick Annie up for a surprise lunch date?”
“I most certainly am, is she around?”
“I’ll check now.” Patrice picked up the phone to call Annie’s boss. As long as Annie wasn’t in the psych ward, Jeff was pretty sure he could charm anyone into letting her go.
“Alright, thank you,” Patrice said into the receiver before hanging up and turning to Jeff. “I’m afraid she’s up at the psych ward, but as soon as she can get Mr. Lowenstein to take his medicine she’ll come down.”
Well damn. Mr. Lowenstein was an elderly man who, for whatever reason, had developed a bond with Annie and refused to trust any of the nurses at the hospital. Even though Annie wasn’t a nurse, she would frequently have to help them administer his medicine, a procedure that took anywhere between ten minutes and two hours depending on how convinced he was that the staff had poisoned his medication.
“Do you know how long she was up there for?” Jeff asked desperately.
“No, but her supervisor said she should be done any minute now.”
‘Any minute now’ turned out to be half an hour later. At that point, Jeff knew he wasn’t going to be able to salvage the proposal so he stayed long enough to give Annie the flowers he picked up on his way over and give her a quick kiss.
5. Holiday Party
“So Jeffrey, do you have any news you would like to share with me?” Shirley asked sweetly during their monthly lunch date at Senior Kevin’s.
“I got my Christmas bonus early and it’s bigger than I expected?” Jeff offered weakly.
“Boy, you know that’s not what I’m talking about!”
“What are you talking about?” Jeff really didn’t like where this was going.
“Britta told me you were planning on proposing to Annie!” Shirley practically announced.
“Geez, Shirley, say it a little louder, I don’t think the people all the way at the back heard you!”
“Don’t you use that tone with me, boy,” Shirley warned.
“Sorry, I’m just trying to keep it a secret. When did Britta tell you anyways?”
“Last Friday.” Great, so when Britta said she could keep a secret, clearly that meant she could stay quiet for three days. She was going to make a terrible therapist. At least she didn’t tell Annie...
“Annie doesn’t know, right?!” Jeff’s brain went into hyper-drive. If Annie knew that would take out the element of surprise and...
“Oh, relax, no one told her.”
“Shirley,” Jeff grabbed her hands “I need you to appreciate just how important it is that Annie doesn’t find out about this before I get a chance to propose.”
“Don’t worry, I won’t tell her.”
“Really? Thank you.” Jeff released her hands, letting out the breath he hadn’t realized he was holding in.
“You’re welcome. Now, did you think of a new way to propose?”
“Not yet. Have any suggestions for me?”
“You should do it at her office holiday party.”
“A holiday party? Really?”
“Yes, just think about it: you’ll both already be dressed up, there will be decorations up, it’ll be perfect.”
“You make a good point but why does it have to be at her holiday party? We’re going to the party at my office tomorrow night and hers isn’t until next week.”
“Because I helped her plan out which dress she’s going to wear and the one she’s wearing to her party is better.”
“What if she changes her mind?”
“I thought we were talking about Annie Edison...” Shirley deadpanned. She had a point, Annie had a tendency to plan outfits out weeks ahead of time, so it wouldn’t be surprising. Especially to a special event like a party.
“Besides, do you really want to propose in front of your colleagues? Are any of them still married to their first wives?” Though Jeff was tempted to point out that most of the married men working at his firm were still with their first wives, but he did agree that Annie shouldn’t surrounded by lawyers only seconds after she got engaged. At least she had some friends at the hospital.
“Alright,” Jeff sighed “I’ll propose at her holiday party.
“That’s nice!” Shirley cheered. “And if she just happens to associate a positive moment in her life with Jesus, then that’s just a happy coincidence.”
“Shirley!”
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“Alright, I’m ready!” Annie called out from their bedroom.
Finally! Jeff had been waiting over an hour for her to finish dressing and primping. Quite impatiently. Ever since Shirley let it slip about Annie’s dress, Jeff had been counting down the days until he could see it.
“Well, what do you think?” Annie asked when she came out into the living room and twirled around, allowing Jeff to get a full look at her dress.
“Wow...” was all he could say. She was wearing a strapless red dress with a satin belt and small embroidered snowflakes. Her hair cascaded down her shoulders in waves and the only pieces of jewelry she was wearing were a gold barrette to keep her hair to the side and a thin gold bracelet.
“I take it you mean that to be a good wow?” Annie asked as she wrapped a gold satin shrug around her shoulders.
“Of course it’s a good wow,” Jeff answered with a charming smile. Shirley was right when she told him to hold off. Not that there was anything wrong with the dress she wore to his office holiday party - a more conservative black dress - it just wasn’t as appropriate for what he was planning on doing. This dress, however, was the perfect dress for a proposal.
“I even got you a present,” Annie said as she presented a small black box from one of the drawers of her desk. “In case you wanted to match.”
“Annie...” Jeff found himself speechless as he looked down at the red satin tie that matched the belt on her dress.
“Here, let me.” She gently pulled his hands apart to stand close enough to be able to remove the tie he was wearing. Jeff couldn’t suppress a hard swallow when Annie’s hand brushed his neck. As Annie worked to put on the new tie, Jeff had to use all of his strength to keep from proposing on the spot and getting to the other thing he had planned for the evening. As much as he loved seeing Annie in that dress, he really couldn’t wait to see her without it.
“I know how much you hate going to these things,” Annie said as she tugged on the knot to secure it, “but it will be over before you know it and as soon as we get home, I’ll make it up to you.”
“That sounds suspiciously similar to the pep talk I gave you before my office’s holiday party.”
“What can I say? I learned from the best.”
When they got to the hospital cafeteria Jeff was even surer that this was the perfect place to propose. Red and green streamers were carefully hung around the room and small LED lights looked like twinkling stars. If there was ever a perfect place to propose - this was it. As Annie made her rounds around the room to greet her fellow coworkers, Jeff went over to the bar.
“Is that your girlfriend?” asked the man who was leaning against the bar when Jeff ordered.
“Yeah.” Jeff couldn’t suppress a proud smile.
“That’s mine.” The man pointed to a taller woman in a blue dress who was animatedly discussing something with Annie. “I’m Greg,” the man added as he offered his hand.
Jeff reached forward to shake it. “Jeff.”
“Nice to meet you, Jeff.” Greg paused to take a drink. “So, how long have you two been together?”
“Annie and I have been together for five years now.”
“Ah.”
“How about you and...” Jeff was sure he knew the name of the woman; he just couldn’t remember it at the moment. It was definitely something that began with an ‘m’. Molly? Mary?
“Maggie,” Greg filled in. “We’ve been together for two years tonight.”
“Hell of a way to spend your anniversary.”
“I know.”
“Here you go,” the bartender interrupted to give Jeff his drinks.
“Well, Greg, it was nice meeting you.”
“It was nice meeting you too, Jeff.” Greg and Jeff shook hands again before Jeff took the drinks and went towards where Annie was standing.
“And then he got us reservations at this beautiful restaurant at the Eiffel Tower. Oh, it was so great! Have you ever been to the Eiffel Tower? You should go, it’s so amazing!” Jeff heard Maggie chirp. The closer he got to the pair, the clearer it was to Jeff that the conversation was very much one-sided.
“That sounds like quite a trip,” Jeff chimed in as Maggie stopped to take a sip of her wine.
“Jeff!” Annie practically cheered.
“Milday,” Jeff gave Annie the appletini he got her. Once Annie took the drink, Jeff took hold of her free hand, ready to extricate her.
“Oh my God! You’re Jeff?! Annie told me so much about you! She’s right, you are handsome! If I wasn’t so happy with my millionaire, I would steal you right up!”
“Speaking of steal, if you don’t mind, I’m going to steal my girlfriend back.” Jeff didn’t wait for Maggie to respond as he pulled Annie away.
“Thank you!” Annie said when they were out of earshot. “I thought she was never going to stop talking!”
Jeff put his arm around Annie, pulling her close.
“She just went on and on about her boyfriend.” Annie’s voice was muffled by Jeff’s body.
“Apparently he’s a millionaire.”
“I doubt he actually has a million dollars but he’s an investment banker so I’m sure money isn’t an issue for them.”
“Hearing also doesn’t seem to be an issue.” Annie lifted her head from Jeff’s chest to shoot him a confused look. “I met him at the bar.”
“Ah,” she nodded and looked around to see that Maggie had already latched onto some other poor soul.
“Want to grab some dinner before she makes her way over to the buffet table and clogs the line?” Jeff asked softly in Annie’s ear.
“Yes!”
The pair spent the next hour eating, having short conversations with some of Annie’s other co-workers, and dancing. Jeff was enjoying himself so much that he nearly forgot about the proposal. As they were dancing to a slow song, the last before the band was set to have a short break, Jeff decided he would propose as soon as the song ended. When it did end, Annie took a step back to look up at him and flash him a smile so full of love that it took his breath away. This was it. This was the perfect moment. The one he had been trying so hard to create for a month and a half. All that was left to do was to finally pop the question.
“Annie...” he started, suddenly nervous. Annie, on her part, continued to smile at him as if he was the most amazing man in the world. He could do this. He was going to do this.
“Maggie?” A familiar voice rang out. Jeff tore his gaze away from Annie to see Greg standing near the bandstand with a microphone.
“Maggie Thompson?” Greg asked again as he walked towards Maggie who was standing only a few feet away from Jeff and Annie, her hands covering her mouth, in stunned silence, probably the first time in her life.
“Maggie Thompson, for the last two years you have made me the happiest man in the world. You’re beautiful, smart, funny, and you have the voice of an angel. Will you please do me the honor--” Greg got down on one knee, producing a ring from his pocket “--of being my wife?”
“Yes!” Maggie screeched. “Oh my God! Yes!”
Well, Jeff’s thunder was effectively stolen. There was just no way he could come back from this. And here he thought he was on good terms with Greg! Looking over at Annie, Jeff could just tell she was disappointed. Even though she was smiling and genuinely happy for her co-worker, because that’s just the kind of person that Annie was, Jeff could tell that deep down she was disappointed.
The whole marriage issue had been a sore point in their relationship from almost the beginning. The fact that a co-worker, whom Annie wasn’t too fond of, had gotten engaged after only two years while Annie and Jeff had been together for five years only made the situation that much worse. In fact, Jeff was actually starting to worry that Annie would break up with him before he even got a chance to propose.
“Hey.” Jeff pulled Annie close to him, placing a soft kiss on the top of her head. “Let’s just go home.”
“In a minute,” Annie responded without looking up at him. “I want to go offer my best wishes to Maggie.”
It took Annie twenty minutes just to get to Maggie and another ten before Annie was able to leave. Jeff wasn’t standing directly next to them, but he was sure he heard Maggie say something along the lines of “don’t worry, he’ll propose someday.” Great, as if it wasn’t enough to ruin his plan, she had to rub the fact that she’s engaged in Annie’s face, too.
Annie was silent on the car ride home, just staring outside the window. Her mood didn’t seem to improve much when they got home. They had slept together, but after five years, Jeff could tell when he was getting pity sex. As soon as they finished, Annie turned to her side facing away from him.
“I’ll make it up to you, Annie,” he whispered as he looked down at her sleeping form. “I promise, I’ll make it better.”
And he would make it better. He’d figure out the perfect new proposal plan, and fast. He just had to. There was no way he could lose Annie.
6. Birthday
Jeff finally had it - the perfect proposal, almost guaranteed to be foolproof. As long as Annie stayed with him for the one week between the hospital holiday party and her birthday, he just knew he could get his plan to work. He even made sure to be the perfect most attentive boyfriend ever. This was phase one of his plan.
Phase two was to have Britta, Abed and Shirley be on the lookout for any signs that Annie was having doubts about the relationship and to let him know as soon as they found out without letting it slip that he was planning to propose.
Phase three was to make sure that no one from Annie’s workplace called her in on her birthday. Annie’s birthday fell on one of her days off but there was still a chance she could be called in and Jeff had to make sure that didn’t happen.
So far everything seemed to be going well. The first few nights after the holiday party, Annie came home later than usual. Jeff wasn’t sure if it was because she was stuck in conversations with Maggie, who was undoubtedly in full-on wedding planning mode, or because she didn’t want to see him. He really hoped it was the former, was almost sure of it, but he couldn’t rule out that it was the latter or maybe even a combination of the two. In any case, Jeff made sure he was home early every day that week in order to make Annie her favorite meals for dinner. He even bribed Patrice to call him as soon as Annie left so he didn’t have a repeat of his second proposal attempt. Thankfully, Annie had gone straight home every day.
The last time the proposal issue had come up she went out with Britta or one of her co-workers every night just so she could avoid spending any time with him. But considering that any time the two were together they could argue, it made sense as to why she wanted to stay away from him. One night it got so bad that she spent the night at Britta’s place. This time was different, thankfully. After the third night of coming home to dinner and a massage, everything went back to normal- for the most part. Jeff could tell Annie wanted to talk about the marriage issue but she clearly didn’t want to get in a fight before her birthday. Still, every day he could see her desire to bring it up. Every day he prayed that she would wait and every day he got more and more nervous.
Now that it was the morning of her birthday, Jeff felt like he was finally in the homestretch. Annie usually woke up at 9 AM on her days off, so Jeff made sure he was awake with enough time to make her favorite breakfast - cinnamon pancakes with whipped cream and sliced strawberries. He turned off their cell phones and the alarm clock, even going the extra step to unplug the landline. Nothing was going to wake Annie up before he was ready.
Double-checking the tray he set up for the occasion, Jeff took a deep breath and went to their bedroom to see that Annie was still asleep. Setting the tray on the dresser so nothing accidentally knocked over, Jeff walked over to the bed and placed a soft kiss on Annie’s forehead. Though her eyes remained closed, Annie’s lips curled up into a smile.
“Wake up, Annie,” Jeff whispered as he placed soft kisses around her face. He didn’t stop until one of her eyes opened.
“Happy Birthday, Milady,” Jeff said before getting up to bring over the tray.
“Mmm, this is the best way to wake up.” Annie smiled as she dug into her food.
“Nothing but the best for the best girlfriend in the world.”
“You’re just saying that because it’s my birthday and you want to be on my good side,” Annie pointed her strawberry-topped fork at Jeff. “But I’ll accept it.”
Jeff merely chuckled in response, experiencing the same flash of absolute certainty he had before his failed proposal at the hospital. If Annie’s reaction to the birthday breakfast was a preview of what married life would be like then Jeff couldn’t wait to finally be able to call her his wife. And it’s not like Jeff was suddenly naïve, he spent enough time around divorce lawyers to know that always doesn’t last, well, always. But with Annie, it was different. Not only was he willing to take the risk with her, he was actually excited to do so.
“Thank you so much for the breakfast in bed,” Annie smiled.
“I’m glad you liked it,” Jeff smiled back. “I hope you like the other things I have planned for today.”
“Jeff Winger planned things? I’m intrigued,” she teased. “What are we doing first?”
“First, I need to ask you something.”
“Ask away.”
“Alright,” Jeff exhaled, suddenly nervous that Annie would say no.
“Annie, these last five years with you have been the best five years of my life. I never thought I could ever love anyone as much as I love you, never thought I was even capable of being in a long-term relationship until I met you, but you have made me realize that I am capable of more than I ever thought I was. I know the timing may be suspicious, but please trust me when I say that I have been trying to ask you this since our anniversary.” Sliding off the bed to get down on one knee, Jeff pulled the ring box out of the pocket of his sweat pants. “Annie Edison, will you please marry me?”
Annie’s eyes went wide as she saw the ring, a four-carat princess cut diamond, beautiful without being too flashy. It had taken him two weeks just to find the ring, but once he saw it, he had known it was the perfect one and bought it on the spot.
“Are you serious?” Annie asked in wide-eyed shock.
“As serious as I’ve ever been about anything in my life.” Jeff tried to keep his voice steady but he knew he wasn’t faring too well. This was it. He had waited too long and now she was going to say no and leave him forever.
“Yes.”
“I’m sorry, could you please say that again?” Jeff was convinced he heard her wrong.
“Yes!” Annie repeated, reaching for the ring box. “My answer is yes!”
Jeff practically leaped forward to kiss her. After two and a half months and five failed proposals, he finally heard the sweetest word in the English language: “Yes”.