After Xander cheated on Cordelia with Willow, a vengeance demon named Anyanka appeared to grant Cordelia a wish. That wish created an alternate reality in which Buffy had never come to Sunnydale, but it unraveled when that world's Giles destroyed Anyanka's amulet. After a thousand years as a demon, Anyanka was mortal again, stuck as a teenager in high school, and oddly drawn to the very guy she came to town to smite. She asked him to the school prom, and he accepted. It was an extremely odd date - Anya spent most of the night telling Xander stories about her glory days as a vengeance demon, full of the myriad ways she had tortured and killed the males of the species. Not exactly the stuff romance is made of.

Knowing her history, Xander confided in her about the upcoming ascension. Anya was terrified - she'd witnessed an ascension centuries before. She told the gang what she could, and then she left to pack her bags. She stopped long enough to ask Xander to go with her - for reasons she couldn't explain, she couldn't bear the thought of something bad happening to him - but when he refused, she hightailed it out of town.

Months later, she returned. She hadn't been able to get Xander off her mind, so she decided that if they just went ahead and had sex, she'd be able to quit thinking about him all the time. The plan didn't quite work out that way. They made a date for a Halloween party, but she arrived late, having to work on her scary bunny costume. She was horrified to discover that the house was haunted, and she ran to Giles for help. Sure, the others were there and in danger too, but mostly she was panicked at the idea that Xander might get hurt.

What followed was an odd courtship full of nightly sex and poorly absorbed lessons in human behaviour. Eventually, she confided in him that she was terrified by her mortal state, and the suave, sensitive half of Xander assured her that he cared for her deeply. But it took seeing Buffy and Riley falling apart to prompt Xander to make sure Anya knew just how deeply he cared. He told her in no uncertain terms that he loved her. As she continued to adapt to life as a human, Anya often clashed with Willow. Anya knew they had been previously involved and was jealous of their close friendship. Willow, on the other hand, seemed to feel territorial about her best friend and admitted that she expected Anya to hurt Xander, just as she'd hurt men for centuries. When a fight between the two women ended up freeing a vengeful troll with a mad on for Anya (and witches), the two had to fight him together. Olaf gave Xander the choice of which woman would die, but when Xander refused, the troll decided to kill Xander. Without hesitation, Anya insisted that Olaf take her instead. Fortunately, Buffy arrived to lay some smackdown, and both survived the night.

Their relationship continued to grow until, just before the battle against Glory, Xander proposed. Anya accepted, but she told Xander to wait to give her the ring until after they'd both survived the battle. Miraculously, they both did, but Buffy sacrificed her life to save the world. She does that sometimes. Xander and Anya seemed to agree that in the midst of such grief was not the best time to announce their engagement, but as time wore on, Anya became more and more irritated by Xander's reluctance to share their news.

Finally (finally!), Xander decided that the moment was right. The gang threw an impromptu engagement party, and Anya was in heaven. Xander, however, seemed to be experiencing mounting panic at the prospect of married life. That panic grew, despite their continued happiness. Then came the wedding day. Anya looked radiant, overjoyed that she would get to spend the rest of her life married to her best friend. Xander, however, looked like a man about to be led to the gallows. A vengeful demon whom Anyanka had once cursed appeared before the ceremony, told Xander he was his future self, and showed Xander a vision of what their future would be. Xander was crushed at how terrible things appeared - they were both bitter and resentful, Anya had clearly had an affair, and when she lit into him for making her so unhappy, he flew into a rage, hefted an iron skillet, and brought it crashing down on Anya's skull.

Despondent over what he'd seen, Xander walked outside in the rain, trying to collect himself. When he returned, he discovered that the vision was a fake, but he still couldn't go through with the wedding. Seeing his parents across the room - involved in one of an endless string of abusive, drunken arguments - Xander couldn't bear the thought of ever being like them, or of hurting Anya the way his parents hurt each other. He just wasn't ready to get married.

Later that day, D'Hoffryn offered Anya her old "job" back. She accepted and became a vengeance demon again. Anya tried to wish harm on Xander, but she needed someone to make the wish for her. All his friends, of course, refused. Spike, however, was a great comfort. He and Anya got drunk together, commiserated about being dumped, and wound up having sex on the Magic Box table. The Hellmouth's sense of tragic timing prevailed again because at that moment, Willow decrypted a video feed that revealed what was happening in the store. Xander was enraged and went to cut Spike's head off, but Anya and Buffy stopped him in time. Then as Xander walked away, Spike finally began to utter a wish. Anya stopped him.

When Buffy went to kill Anya, whose vengeance work had begun ringing up a body count, Xander tried to intervene. She told D'Hoffryn to take her powers away again, and afterwards, she and Xander began spending more and more time together, as Buffy's house became their new headquarters. They had what Anya called 'break-up sex' - a last time together - but it actually wasn't. With the final battle looming, their feelings for each other were still clearly there. They slept together again, seemingly on the verge of being 'back together', but that final battle claimed Anya's life.

Pivotal Episodes:
The Wish, The Prom, Graduation Day I, The Harsh Light of Day, Fear Itself, Hush, Where the Wild Things Are, The Replacement, Into the Woods, Triangle, The Gift, All the Way, Once More With Feeling, Hell's Bells, Entropy, Selfless, Touched

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