Xander Harris is my favorite male character on a female driven show; Joan Holloway is my favorite female character on a male driven show. Their common struggle to negotiate their desire for success even though they’re playing in an opposite-gendered tree house defines both characters. Moreover, Joan and Xander “succeed” against their gendered odds. Xander is the one person and certainly the only male character who ha been a consistent and present ally in Buffy’s life, always fighting by her side, since Day 1. Joan is the one female partner in SC. Even before that, Joan was the only woman had a purely managerial position since Day 1.
Of course, Xander and Joan’s situations are very different. Joan is completely barred from fair and equal treatment at SC 1.0/SCDP/SC 2.0 because of her gender. The men of SC and SCDP have all had different legit opportunities to promote Joan for exemplary performance (her talent at reading TV scripts and how clients loved her for it, her getting in on the ground floor of SCDP and enabling the agency to start, her performance in the middle of disaster when Lucky Strike left) and have pretty much always turned it down until they needed to rent out Joan’s body to get Jaguar. The 1960s culture was highly sexist and SC in its various iterations is a highly sexist company. To say nothing of the fact that Joan didn’t get to spend her most formative years through her teens and twenties developing herself as a business-woman because Joan had the misfortune to be born too early before the sexual revolution of the late 1960s.
I do believe that there’s a real concrete problem where large swaths fandom treats Xander like shit because he’s a man with man parts with opinions and human failings. However, Xander’s *actual* friends don’t reject Xander like Joan’s colleagues reject her solely on the basis of gender. That said, Xander does suffer a little from the fact he speaks Martian and Buffy/Willow speak Venetian. More to the point, guys like Larry or Jack o’Toole or Blaine disparage Xander for breaking Teenage Boy Rules because he hangs out with Buffy and Willow just to be their friend without scoring. And in so doing, Xander ends up living the action hero life of coolness and purpose that dudes like Percy or Blaine only think exists in comic books. Xander takes a significant opportunity cost socially and career-wise for being in the Scooby gang which is really not brought out enough on the show or in fandom conversations. Part of that is that Xander being Buffy's and Willow's best friend is a hit on his masculinity to the rest of the guys in the world.
Not for nothing but in my personal canon, Xander often felt a tug of war as a child between being Jesse's best friend and Willow's best friend and that's where Willow got the "Xander is my best friend"/"We haven't always been close" dichotomy. And Xander actually tilted toward spending more time with Willow, especially as a child, because that's where his heart was but he did feel social pressures to spend more time with more socially adjusted, same gender Jesse.
Also, Joan’s only started to demand full respect from her male compatriots in S4 and particularly when she became a partner at the end of S5. In S1-3, Joan merely asserted control over the secretaries while being constantly being condescended to by the men. Xander pretty much walked into the Scooby gang demanding respect and attention to his ideas from Buffy. This is the case for a number of reasons. Xander fought shoulder to shoulder in what started out of a close-knit gang of four. In S1-3, Xander took on a lot of Buffy’s risks, the equivalent of Willow’s risks and IMO, *more* risk than Giles. Joan, meanwhile, was a secretary bent on earning her paycheck and hanging around in NYC to get married. She wasn’t taking on the risks that the partners take on or investing the time that creatives or account executives do. And as always, Xander walked in with an expectation of being treated fairly regardless of his gender (as the man says, that pesky all men are created equal thing) and even expected to assume a great role due to his male privilege. Joan walked in SC expecting to be treated UNFAIRLY because of her gender and she’s only recently realized how she was short-changed.
As such, Joan coped in the earlier seasons by holding her tongue on her male colleagues’ shenanigans. Joan would try to control stuff as best as she could by punishing her secretaries under her jurisdiction for OTT pranks and unprofessional behavior even if the men participated or instigated or trying to control things like the keys to the liquor cabinet and client assignments to different account boys. Meanwhile, Xander coped with his disapproval over Bangel or even Willoz in the earliest eps by outwardly snarking. Xander felt no need to hold his tongue- he’s got opinions and he’ll damn well express them! IMO mostly for bad, Xander was badly burned in group respect for too loudly vocalizing his Bangel disapproval and his disapproval over some of Buffy's coping mechanism (running away and never phoning home for three months). Later seasons show Xander taking more of a Joan-approach to his disapproval which consists of gossiping behind someone’s back (frequently re: Willow and magic), pretending like he doesn’t disapprove and participating in pursuing a risky option aimed at preserving one of Buffy’s boyfriend (focusing on curing Angel in Amends instead of looking into whether he’s dangerous), exploding at Angel or Spike pointedly when Buffy isn’t in earshot to yell at him about it and never mentioning his issues back to Buffy, or holding his tongue until he REALLY explodes ala Into the Woods or Entropy. By contrast, Joan has actually started more and more to confront the men of SC now that she's a partner and to drop some of the kick downstairs/kiss upstairs garbage.
Joan and Xander are reliant on their different-gendered group for favor compared to some of their same-gendered compatriots. Joan is an administrator- her whole work product is how she handles a group. She’s not a mega-creative like Peggy who comes up with creative ideas and can be attractive to employers just based on her ideas. Joan isn’t even a Faye who isn’t quite the special snowflake of a creative but can certainly whack sexist jerks on the head with her fucking set of degrees. Xander isn’t a super-powered vamp like Angel and Spike with centuries of experience in going off on lone-wolf missions to kill and maim and destroy or a super-soldier like Riley with an entirely military complex as a safety net. Xander occasionally lone-wolfs it but only because Xander feels that he HAS to in order to save lives ala The Zeppo. And even in Prophecy Girl, Xander would rather bite the bullet and get *Angel’s* cooperation and share credit with *Angel* than run the risk of lone-wolfing it. IMO, it’s under-discussed but Xander’s renowned bravery is made all the more impressive by the fact that he has a keen self-preservation instinct and he’s defiantly NOT suicidal by any means. When Xander does lone-wolf it for emotional reasons, he reproaches himself. (Hey, Giles, here's a nifty idea: why don't I alleviate my guilt by goin' out and gettin' myself really, really killed?) Seriously, most Buffyverse males have been driven to crazy danger based on their guilt; Xander is the only one with the self-awareness and mental health to verbalize it and identify this instinct as a problem.
Given that Joan and Xander are bound to working with their different-gendered group, they modify their behavior to make it work.
Facially, Joan got her seat at the boardroom table because she is *so* feminine. Facially, Xander got his seat at the Bollywood movie, in Willow’s and Buffy’s room and as a full-fledged Third Musketeer even if he’s the minority gender partly because he’s not so masculine to be threatening or to drop his female best friends like bad habits because he's not getting sex from them. However, further consideration reveals that Joan and Xander use both feminine and masculine traits. Moreover, the way that Xander and Joan integrate both traits, indicating that the line where bravery and competent management is “masculine” while listening and compassion is “feminine” serves no useful function. They bleed enough into each other that we should really consider all of these traits as "androgynous".
People will label being “neat” and “organized” and “focused on appearances” as feminine while being “good at math” and “having a head for business” as masculine. However, Joan employs all of those traits in tandem in her job. Joan both budgets the SC/SCDP office to appear as streamlined and professional as possible even when they’re in the financial dumps AND offers the secretaries fashion advice and plans wild parties partly to again, ensure that the offices appear as streamlined and modern as possible even on a shoestring budget. At the same time.
Meanwhile, facially, Don and Roger confide in Joan more than the other secretaries and bring her to parties and Cleo Awards because Joan is aces at being feminine. Certainly, Roger drew closer to Joan because of their affair and because Roger remains incredibly attracted to Joan. Don feels protective of and kindly toward Joan because Joan is beautiful and because IMO, Joan pings Don’s childhood prostitute issues. However, Joan continues to get her foot in the door for her strength and business skills that folks that Don and Roger would call masculine. It creates a paradox in how the men of the agency treat Joan. Bert Cooper knew to call Joan to send out notices to SC’s clients when Roger had a heart attack because Bert knew that Joan would be able to calmly and efficiently handle this task late at night, even though Bert also knew that Joan was sleeping with Roger. But then, Bert felt entitled (admittedly, IMO, with good intentions) to lecture Joan in a grandfatherly way to not waste her youth on older men like Roger…because Joan’s youth is a verrrry limited commodity that needs to be applied to getting married ASAP.
Meanwhile, Xander applies his stereotypically feminine unconditional love and understanding to his masculine bravery- but the two are such natural outgrowths of one another that it renders the gender classification meaningless. Is Xander more brave in a masculine way for diving into hell to save Buffy or is he more feminine for having the forbearance to rescue her even though he feels wounded by her? Is Xander more brave in a masculine way for staring down Dark Willow or more feminine for loving her so unconditionally? Who knows and who cares? The two are the same. Moreover, the gender motivations twist and turn in The Zeppo. Xander achieves a rite of passage for teenaged boys in standing up to his bully, Jack O’Toole and his wins the classically 1950s contest of chicken. James Dean in Rebel Without a Cause would be proud. However, Xander’s ultimate role is to keep the homefront of SHS safe so that the rest of the Scoobies could go off and fighting their inter-hellmouth flashy war. In war culture, Xander is the woman on the farm fighting the marauders and slash and burn barbarians so that the men fighting the glorious war that’s going to land in the history books have a home to come back to.
As Buffy spell-drunkenly said, she loves Xander because he so totally and completely one of the girls! And Xander *does* accumulate valuable social bonding time with Buffy because Xander is totally cool doing girly stuff that Buffy likes to do- shopping, watching foreign films while braiding Willow’s hair, playing Anywhere But Here while fantasizing about a celeb, getting excited about dressing up for different dances or Halloween, gossiping, etc. Many teenage boys would turn up their nose at doing those kinds of social activites. Not Xander. That consistent networking serves a useful function. It’s part of why Xander is so clued into Buffy and Willow. That forces Xander’s inclusion into evil-fighting activities and decision-making where his lack of powers or minority opinions would exclude him.