Dan Humphrey is a romantic whose imagination runs wildly at the worst times. He over-analyzes life and can grow easily frustrated.

This young hunk is best friends with Vanessa Abrams (Jessica Szohr) and the big brother of Jenny Humphrey (Taylor Momsen).

Dan Humphrey has been head over heels in love with socialite Serena van der Woodsen for many years, and finally snagged his dream girl in the first season of Gossip Girl.

The adorable pair soon began dating and - after some initial difficulties - made love for the first time on Christmas.

However, their differences in social class - as well as her shady past and characters like Georgina Sparks - have driven them back apart.

An aspiring writer and fairly straight-arrow guy with a good heart and morals, Dan maintains his close relationship with his sister, Jenny and his father Rufus. He does not really fit in with Nate or Chuck, though he and the former seem to get along better than he does with the latter.

Dan Humphrey Quotes

Blair: Fashion is the most powerful art there is. It's movement, design and architecture all in one. It shows the world who we are and who we'd like to be. Just like your scarf suggests that you'd like to sell used cars.
Dan: Vanessa gave me this scarf.

Dan: [on phone, walking away] I don't like lying to my girlfriend. Serena has a right to know what's going on.
Isabel: Oh my god, we have to tell Serena.
Nelly: Tell her what? We don't know what he's lying about.
Penelope: Why are you talking? Last I checked you were still on probation.

Gossip Girl Quotes

And who am I? That's one secret I'll never tell ... You know you love me. XOXO, Gossip Girl

Gossip Girl

Chuck: I'm sorry for losing my temper the night you told me Louis proposed to you. I'm sorry for not waiting longer at the Empire State Building. I'm sorry for treating you like property. I'm sorry I didn't tell you I loved you when I knew I did. Most of all I'm sorry I gave up on us when you never did.
Blair: Thank you.