Timeline: S1-S5

[hells_half_acre]

---SEASON 1 ---

October 31st/November 1st, 2005 - Dean arrives in Palo Alto - quite late at night. The boys spend 2 days investigating a Woman in White in Jericho, California. (Pilot)

November 2nd/3rd 2005 (2:50-3am) - Jessica dies. Sam and Dean hit the road.
-Time taken from unaired Pilot scene.

~November 10th 2005 - Sam and Dean arrive in Lost

Comments

[hells_half_acre]

Haha, I like your icon.

Glad you like the timeline!

Unfortunatly, I don't think they give much away in the show about when Dean dates Cassie. (I should probably have her in there though.)

Here is what I CAN tell you about Cassie, that might make it easier to narrow down:
-Dean dated her while she was "just finishing up college". As I doubt that there is a college in Athens, Ohio, we can assume that it must have been a holiday in order for her to be home at that time.
-Dean dated her for a "couple of weeks" - so, it was a long holiday. Possibly Christmas, possibly an extended Spring Break. (If he dated her in the summer before her final year, I doubt that he would say she was "just finishing up", though maybe he would, so that's an option to.)

So, sadly, all I can really narrow down is the time of year he might have dated her (Christmas-Spring Break)...but not necessarily the year. Personally, I would probably place it about at the half-way mark of the four years that Sam was gone...but that's just personal opinion. It gives plenty of time for Cassie to finish school and get established at her newspaper job.

I don't have my DVDs with me at the moment, but when I get them back, I'll double check the episode to make sure there's isn't anything I'm missing.

[epicallytired]

Yeah, we're on the same page. Dean admits it was "more than a few weeks" so Winter break, (5 weeks) or possibly summer might make more sense.

I think it was the same year Sam was a freshman at stanford, and on Winter Break, so she'd be starting the "spring semester" of her senior year... but thats based on far less detailed viewing than you've done.

SUN (Shutting Up Now)

[hells_half_acre]

I just realized that there IS a University in Athens, Ohio - Ohio University. It occurred to me to look it up, because Cassie doesn't actually LIVE in Athens, Ohio, in the episode. She's in Missouri.

So...that actually blows my narrowing-it-down-to-time-of-year out of the water. So, it's probably sometime in the Spring, while she's still at school.

[epicallytired]

so spring of senior year, athen's ohio, cassie and Dean, and it has to be spring of sam's freshman year.

well, by has to be, i mean, i strongly believe based on my psychological deconstruction of Sam, Dean and SamandDean

[hells_half_acre]

Yes, I think based on psychological deconstruction, it's completely reasonable to assume that it's the spring of Sam's freshman year. I mean, there's the off chance that it could be sophomore...but I think freshman makes more sense.