Nate Archibald (Chace Crawford), the golden boy from "Gossip Girl" is considered one of the most attractive young men of the Upper East Side. His father is Howard "The Captain" Archibald (Sam Robards), a very successful business magnate and his mother is Anne Archibald (Francie Swift), a member of the Vanderbilt family. Nate's best friend is Chuck Bass (Ed Westwick) and they both attend St. Jude's School for Boys. Nate has had an on and off again relationship with Blair Waldorf (Leighton Meester) since Kindergarten, but he's always had secret feelings for Serena van der Woodsen (Blake Lively) who is actually Blair's best friend. He finds Serena drop dead gorgeous and even had a one night stand with her.
Nate bumps into Serena and they talk about summer plans on the Season 1 season finale. When Season 2 starts they tell everyone they have spent the summer together, which later is revealed as a lie. The lie was to cover up that Nate was actually dating a much older married woman by the name of Catherine Mason (Madchen Amick) who coincidentally is Blair's new boyfriend's stepmother. It comes out later that Nate and Catherine are exchanging sex for money, because the Archibalds' assets were frozen after his father fled the country. Nate tried to leave Catherine for Vanessa Abrams (Jessica Szohr) but Catherine confronted Vanessa and told her she would reveal Nates' dad's whereabouts if he did not stay with her.
At a party thrown at his grandparents' home, Nate finds Blair drunk and acting completely out of control because Chuck rejected her. He comforts her and they reconnect their friendship. Vanessa, who he is dating at the time felt that it was more than that and confronted him about it. Nate broke up with Vanessa because he was upset that she couldn't trust him, although he felt that it was more than friendship as well. He asks Blair to move in with him but she never answers.
In Season 4, Chucks' little black book is revealed and it tells all about Nates' tons of one night stands. Later on in the season, Nate meets a girl named Juliet Sharp (Katie Cassidy) who he quickly falls for, but he starts to get suspicious thinking that she is hiding something from him. After Nate leaves Juliet, Dan and Nate both decide to win back Serena. Unfortunately Jenny (Taylor Momsen), Vanessa, and Juliet, all of his ex-girlfriends, sabotage his relationship with Serena. Nate reveals that he still loves Serena after she goes to rehab but he is going to move away.
"I mean, if you want her, then man up and tell her. Otherwise you gotta cut her loose. And you gotta do it for real this time, man, because I want her!"
"I'm out buying you some new clothes. I know you've been locked away for a while, but no one's wearing orange this season."
"So you said you loved her? That's um... well never heard you say that before, about anyone."