Xander's Relationship History

Willow: Willow and Xander have known each other practically since birth. They even "dated" for a while, but broke up because Xander stole Willow's Barbie (they were 5 years old). Of course, that's only Willow's side of the story. There then followed a period of some 10-15 years of Willow harboring unrequited love for Xander, and Xander pretending he didn't notice ... except for one brief period when they were all over each other, despite the fact that they were both in other relationships at the time (Willow with Oz, Xander with Cordelia). They got caught by their significant others, and felt very very guilty. There's been very little indication since then that anything but platonic friendship exists between these two, but at the end of Season 6, a grief-stricken Willow was only restrained from destroying the world by Xander's unconditional love for her. It's uncertain where this will go in Season 7, but given Joss Whedon's descriptions of the theme of Season 7 as "Buffy: Year One," I'm rather hoping that we will finally see Xander and Willow happy together.

Buffy: Xander has had an unrequited crush on Buffy since the first moment he saw her in the first episode of the series. He even asked her out once, when they were still at Sunnydale High, but she said no. Since then, they basically haven't talked about it, and Buffy pretends that it doesn't exist. But Xander has continued throughout the series to vigorously beat his chest around any other male (be they human or otherwise) who shows romantic or sexual interest in Buffy.

Praying-Mantis Lady: While at Sunnydale High (in only the fourth episode of the series), Xander felt flattered by the attentions of an extremely sexy science teacher named Miss French. She invited him over to her house, apparently for some nookie ... but she turned out to be an evil praying-mantis lady who just wanted to use a virgin male for fertilizing her eggs, and then kill him afterward. Luckily, Buffy saved Xander by killing Miss French, and they all swore never to tell anyone that he was still a virgin.

Inca Mummy Girl: Xander's first real relationship on the show was with "Ampada," a beautiful foreign exchange student staying with the Summers family. Unfortunately, Ampada turned out to be an ancient Incan mummy who had to suck other people to death almost constantly, in order to stay alive. That put a damper on their relationship, especially when Ampada tried to suck Willow to death. Xander couldn't let that happen, and so Ampada died a very dusty gross mummy death.

Cordelia: Cordelia, Willow, and Xander have all known each other pretty much forever. In fact, Xander was at one time Treasurer of the "We Hate Cordelia" club, and snobby Cordelia in turn considered Xander and Willow losers beyond redemption. In one of the more shocking relationship moves on the series (certainly more shocking than Willow turning lesbian), Xander and Cordelia "dated" (i.e., alternately kissed and fought) for about a year at Sunnydale High (eps. 2.10-3.08). When Cordelia saw Xander kissing Willow, turned to run, and ended up nearly dying from getting impaled on some rebar, she suffered enough hurt and trauma that she never really got over it. Their relationship ended for good.

All Women in Sunnydale: Before the final end to their relationship, however, Cordelia temporarily broke up with Xander because her popular friends thought he was a dork. Xander persuaded Amy to perform a magic spell to make Cordelia fall back in love with him, but it backfired to cause every woman in Sunnydale except Cordelia to want him. This included Buffy's mother Joyce, the vampire Drusilla, Giles' love interest Jenny Calendar, and Buffy herself ... who tempted Xander almost beyond endurance. Luckily, Giles ended the spell before anyone was seriously hurt, maimed, or compromised.

Faith: Not too long after the end of his relationship with Cordelia, Xander lost his virginity with the new-bad-girl-in-town, the slayer Faith. When he tried to be nice to her afterward, though, she tried to kill him. Guess that'll teach him! Luckily, Xander was rescued by Angel (of all people).

Anya: Anya -- formerly the demon "Anyanka," but now stuck in a human body -- developed quite a yen for Xander and relentlessly pursued him until she finally caught him. Though their relationship started out as purely sexual, it grew into something much more close and committed. In fact, at the end of Season 5, Xander actually asked Anya to marry him ... but several months later, he humiliated her by stranding her at the altar (because he was afraid that he would mistreat her the way his father mistreated his mother). In her pain and fury, Anya decided to become a demon again ... and Xander has an extreme prejudice against all demons. Then, just to put the icing on the proverbial cake, Xander discovered Anya seeking solace in the arms of Spike ... the demon Xander seems to despise above all others. Chances don't look good that Xander and Anya will patch things up, but on this show you never know what's going to happen.