Authors Note; Okay, let's try something different, for now. It's still a matter of shaking your hat, but this time we've got one name and the five people they will be paired with. It's all in order, so that the last name I pick, is the last and final pairing this person will get. Get it? Cool, let's do it.
I should mention, quickly, that all five pairings don't necessarily mean romantic and serious relationship. It can be f*ck buddies, one-night stand, and on rare occasion, though I despise it, it can even be rape. But it just has to be worthy of the name, pairing, meaning sexual in some fashion. Thank you.
The haughty, stick-up-his-butt Wesley arrives in Sunnydale to take over as Watcher for both Faith and Buffy, during the third season. What he doesn't expect is to find himself going against Council law, when he meets an enchanting Vampiress, by the name Drusilla the Mad. Dru returns to Sunnydale to search for her Dark Prince, not knowing that Spike has already left again, after Lover's Walk. Then she has yet another vision and finally comes to terms with the fact that Spike doesn't belong to her anymore. So, she decides that she wants another Prince to take care of her and that becomes Wesley.
The Watcher tries to fight her off at first, but for the life of him can't explain why he keeps Drusilla's presence a secret, or why he doesn't tell Giles of her insistence that he become like her; a Vampire. And it doesn't even have anything to do with her thrall, it's more of a strange, but human, attraction to the beautiful brunette. Whether it moves into the sexual territory is up to you, but there should be more than one kiss and an emotional bond that doesn't break until Dru is either staked or leaves town; again, up to you.
When summer rolls around, Wesley is fired and can't afford to fly back to England, so he stays in the California area. While Angel is busy brooding in the dark, Wesley has several run ins with Doyle, who has only recently started getting the visions. Wesley tries to help the young man come to terms with his half-breed blood and his new connection to the Powers and through it the two form a close friendship. Unfortunately that is completely destroyed by a drunken one-night stand, after both men drank away their misery and wound up in bed together, both curious about same-sex... sex.
No idea that Doyle is currently working with two people Wesley knows very well, though not as well as he knows Doyle hehe, Wesley buys an old motorcycle and decides to travel for his Demon hunts. In one of the many Demon bars across the country, the young Watcher finds himself facing a very familiar face; Oz. Apparently the werewolf was forced to leave Sunnydale, when he lost control of his animalistic urges and he's now trying to find a place where he may get a cure; explaining his presence in said Demon bar.
The two men share more than a few drinks and a few kisses, before going their separate ways, after Oz learned of a Tibetan Monestary. And then canon peeks its head out, when Wes returns to Los Angeles and takes Doyle's place in Angel Investigations. Years pass and Wes has been ostracized by his old friends, after the whole deal with Connor. Unlike the show, he will not be welcomed back when the sun is blotted out. Instead, he decides to leave Los Angeles behind, for greener pastures. Let's just assume, for the moment, that in order to get to San Francisco, or something, Wesley has to pass by Sunnydale.
He has switched out his bike for a used car and decides to pick up the young hitchhiker he sees on the road leaving the Hellmouth. Her name is Cassie Newton, she's seventeen and desperate to see the world, before she is supposed to die next year, during canon S7 of Buffy. Although she doesn't tell Wesley that last part. Now, I know what you're thinking; ew, he's almost old enough be her dad or it's illegal or whatever. All I can say is, puh-lease; if Angel can boink Buffy then Wesey can certainly date Cassie, kay...
Anyway, the two fall in love, despite age differences and Cassie decides to stick with Wes, thinking she might be able to use her 'gift' to do some good, before her time is up. Unfortunately, because of how fragile she knows Wes is, she never tells him about her expiration date and when it arrives, it's all he can do not to let a Vamp or Demon have its 'one good day'. But the past few years of heartbreak, disappointment and loneliness are about to come to an end, when he arrives at a town or city of your choosing. One that happens to have an old face; Detective Kate Lockley.
The final love story is all up to you, but it has to be the one that lasts.
Also, you obivously need to fill in the holes I've left; like what happens when Wes and Cassie are on the road, what the thing with Dru is like and so on. Make it a good, lengthy story, with lots of angst, tears, laughter and warmth, that eventually leads Wes to his true love.