Serena van der Woodsen is smart and super pretty ... but is constantly being told she is not working to her full potential.

Serena van der Woodsen is also surprisingly vulnerable, despite seemingly having it all together on the surface.

Like Blair Waldorf, her best friend (but with whom she has a strained relationship) Serena and her family are prominent in New York society

Given her beauty and personality, Serena enjoys a steady string of admirers, namely Dan Humphrey (Penn Badgley) and Nate Archibald (Chace Crawford) at present, but also numerous others in the past.

After a scandalous affair with Nate - who was dating Blair Waldorf - Serena left N.Y.C., only to return a year later under a cloud of suspicion.

The subject of their secret - or not so secret - hookup remains sore and mysterious for Blair and others. But it turns out Serena left for another reason: A guy she was hooking up with overdosed on drugs and died while her friend Georgina Sparks filmed the whole thing.

Georgina later resurfaced and when Serena would not reenter their old, wild lifestyle, G threatened to blackmail her with the tape.

S then came clean about the overdose and ultimately G got hers - thanks to a little help from Blair and Chuck Bass, whose father Bart married Serena's mom in the season finale.

Despite the attention she receives from the opposite sex, Serena constantly longs for real romance... which she eventually finds with Dan Humphrey, a middle class guy from Brooklyn who sweeps her off her feet with is genuine charm.

But her web of lies and distancing herself over the situation with G - who also tried to meddle with Dan - scared him away, and the two are not together... at least for now.

Serena has one younger brother, Eric van der Woodsen, and lives with her mother, Lily van der Woodsen, as well as her new stepfather, Bart Bass, and stepbrother and friend, Chuck Bass.

Serena van der Woodsen Quotes

Serena: I don't know. I had enough trouble with the idea of mom and Rufus dating, but now I share a sibling with my boyfriend. That's little more hillbilly than I can handle.
Eric: It is a little twisted. But so what?
Serena: Well what if we can't get past it?
Eric: I don't know. But you can't push Dan away right now. Whatever you are going through he's going through the same thing.

Blair: As for your devoted suitors, have you finally decided whom to crush?
Serena: No, and I have feeling for both. I don't want to hurt either. I have a whole new appreciation for Big Love.
Blair: Well. Even in Utah only the men get to have more than one spouse. Which, I've come to realize, is extremely sexist.

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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

[to Jenny] That's the thing. You need to be cool to be queen. Anne Boleyn thought only with her heart and she got her head chopped off. So her daughter Elizabeth made a vow never to marry a man. She married a country. Forget boys. Keep your eye on the prize, Jenny Humphrey. You can't make people love you, but you can make them fear you. For what it's worth, you're my Queen. I choose you.