As we learned in "Spin the Bottle," Wes was 'Head Boy' at the Watchers' Academy in England - though he had never actually fought a vampire under anything other than 'controlled' circumstances. From this episode, as well as other comments found in various other episodes, we can deduce that Wes led a sheltered, possibly wealthy life. From "I've Got You Under My Skin" and "Lineage," it is clear that Wes has a more than strained relationship with his father. It is implied that Wesley's father abused him - emotionally and verbally, though possibly even physically, and some fans even believe that sexual abuse was present as well.

We first met Wesley in "Bad Girls," when he was assigned as Faith's Watcher. His character at this point was a simply a product of his upbringing as well as his education at the Watcher's Academy - he pretends to know it all to make up for the fact that he really has no idea what he's doing. He's incredibly insecure - a direct reflection of how his father treated him. He's stuffy and way too by-the-book. The Scoobies, as well as Giles, ignored him when they could - no one actually liked him. Well, no one except for Cordelia, who in all honesty was probably just trying to get back at Xander for cheating on her with Willow - but their mutual admiration ended when they shared a disasterous kiss in which, according on Cordelia in "Birthday," Wes drooled all over her chin.

During the summer after getting fired from the Watcher's Council due to his immense failure as Faith's Watcher, Wes became a Rogue Demon Hunter - and even dressed in leather. In "Parting Gifts," he arrives in Los Angeles while tracking a demon. When the demon is taken care of, he plans to leave, thought it's clear he doesn't want to. Angel, recognizing this, invites him to stay. Through the next few episodes Wes found his place in the gang, and slowly but surely gained confidence. He acted mainly as researcher of the supernatural, as well as translator of languages, and other intellectual things - though he wasn't above risking his life for his friends. One such time, only a handful of episodes after his arrival in Los Angeles, was at the hands of Faith, his former Slayer. She tortured him viciously, and he withstood it without the slightest whimper - a testament to how strong, not really physically, but emotionally, he had become.

Wesley's first actual relationship (as opposed to fizzling lust) on the show occured in season two, when he met Virginia Bryce in "Guise Will Be Guise." Wesley was disguised as Angel, but it was all Wes that saved her, and that she chose to be with. When Angel turned dark, Wesley took the leadership role, doing what Angel should have been doing instead of chasing Darla. Wesley led Cordelia and Gunn in protecting people from evil. It was while trying to save Gunn that he got shot almost fatally in "Thin Dead Line." When Angel returned back to the good side, he deffered to Wesley. Wesley continued to call the shots - proving he's far from the insecure, bumbling man he once was. When Virginia expressed her fear of the violence surrounding Wesley's life, Wes realized the relationship had to end - and he broke it off with her, parting from her with grace and maturity.

By the end of the second season, Wesley's character was one who had confidence, maturity, and knew his place in the world. He was able to lead an army of rebels in Pylea, making tough strategic decisions to win. Even Gunn had been amazed at the intiative he took. In the third season of Angel, for a majority of the first part of the year, Wes spent time swooning over Fred - a character who had been trapped in Pylea - and competing with Gunn for her affections. In "Waiting in the Wings," she chose Gunn, leaving Wes to, well, wait in the wings. Meanwhile, Wes had been translating a prophecy - later proven to be false - about 'the father killing the son,' and fearing that Angel would do so, Wes did what he thought was right, kidnapping the newborn Connor.

This is when Wes enters an extremely dark period in his life. His attempt to save Connor ended up with Connor taken from him and sent into a hell dimension, and Wesley with his throat cut. Angel, quite understandably, was beyond angry at Wesley, and the rest of the gang pretty much took Angel's side. Wes was shunned by his only friends and makeshift family and left to wallow in his own regret.

In comes Lilah, the evil but charismatic lawyer with Wolfram and Hart. Their relationship started as pure sex, but later developed into something more. Both refused to say "I love you," but it was clear feelings were present. Wesley - and I say this in a loving way, because I love Wes, and I love Wes and Lilah together - was pretty much a bastard to Lilah, and increasingly towards the end of their relationship, when he broke up with her leaving her to limp out of the sewer with a gut wound alone and with nowhere to go.

By that time, Wes had begun speaking to AI team again, and he helped the gang during the big Jasmine plot - slowly but surely integrating himself into the gang again, and by the end of the fourth season, Wes was part of the team again - and joining them at Wolfram and Hart when Lilah returned from the dead to offer it to them.

As Wesley tried to become accustomed to Wolfram and Hart, things headed in a newly dark direction for Wesley. What he thought to be his father came to the office, in "Lineage," supposedly to assess him and then, possibly, offering for him to come back to the Watchers' Council. The whole time his "father" (Roger Wyndham-Price, in case you were curious) was there, he belittled and went out of his way to embarass Wesley, and even attempted to knock him out by pistol-whipping him. Parent from hell, right? Well sort of. Wesley came to, and found his way to his father. Wesley had a gun, and he used it without a moment's hesitation when his father threatened Fred. He didn't just shoot his "father" - he emptied the entire clip into him. Wesley realized what he had done, and went off to vomit - and then he heard an electrical buzzing behind him. He turned around, and saw that it hadn't been his father at all, but a cyborg.

Angel and Spike both tried to comort him with the fact that they, too, killed their parents - but it really didn't work. Finally, Wesley does what he feels he has to do - he calls his father, telling him he just wanted to see how he was doing. It's unclear just how deeply this has effected Wesley, but it looks like there's more angst in store for our favorite former Watcher.