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.

Blair [to Chuck]: Because it made me realize I wanted to be with you. Dan and I both know it meant nothing—less than nothing. Right?
Dan: Yeah, that's right.
Blair: I was going to tell you all about it tonight. But that would have been a huge mistake. Dan Humphrey may not be royalty but at least he's not a child.

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

Sometimes you need to step outside, clear your head and remind yourself of who you are. And where you wanna be. And sometimes you have to venture outside your world in order to find yourself. As for me, I'm happy right where I am. I only wanna be with you. xoxo ... Gossip Girl

Gossip Girl