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This Is Dan's Best And Worst Trait On Gossip Girl

On Gossip Girl, it was natural for a character to be your friend one minute, and your enemy the next. 

The show, which charted the lives of Manhattan's Upper East Side teens, depicted a social ecosystem full of back-stabbing and double-dealing, where relationships and reputations were consistently on the rocks. If one character was initially meant to stand out as "different" from the rest, immune to the petty behaviors of the elite, it was Dan Humphrey. Played by Penn Badgley, Dan was, in a sense, a stand-in for the audience — an outsider living in Brooklyn (gasp!) who watched the lives of his upper-crust classmates with disdain. Of course, it's quickly revealed that Dan is just as fascinated by them as we are, even seeking to join their ranks. If you count the fact that — spoiler alert — Dan himself is Gossip Girl (a plot point that most of the cast and fans find absurd), his character is further unmasked as an obsessive chronicler of the lifestyles of the rich, going so far as to ruin multiple people's lives, including his own, as well as his younger sister Jenny's.

Even without the bizarre reveal at the end of the series, Dan is a character full of surprises. Unlike most of the characters on the show, he doesn't change from sweet to sour at a moment's notice — his is somewhat of a slower evolution. While Dan's better traits are on display early on, as he courts beautiful it-girl Serena van der Woodsen (Blake Lively) and stands up to sleazy womanizer Chuck Bass (Ed Westwick), it's not long before his true nature comes to the fore, and we realize that Dan is just as bad, if not worse, than the rest of the cast. Here are Dan's best and worst traits on Gossip Girl.

Dan's awkwardness can be endearing

Also known as "Lonely Boy," Dan has that particular brand of nerdy charm that takes people by surprise. Namely Serena, the seemingly aloof and impenetrable socialite and scenester who falls head over heels for Dan's unassuming attractiveness. 

Starting off the series as the guy "nobody knows," Dan's crush on Serena ultimately pays off, as she sees him as an escape from the callousness of the popular boys she knows from school. Dan's rise in popularity, as well as his on-again, off-again romance with Serena provides the backbone for much of the show's six seasons, which ran from 2007-2012, and proves that Dan can certainly be a loving and romantic boyfriend at times. Clearly there's something girls like about him, since he goes on to date many other characters on the show, from the obvious pairing with his artsy childhood best friend Vanessa (Jessica Szohr) to his strange and unlikely coupling with queen bee Blair Waldorf (Leighton Meester) herself. But while Dan's character can be charming at times, his worse qualities often get in the way of his relationships, and his overall like-ability.

Dan's worst trait is his insecurity

Behind Dan's seeming indifference to the antics of the "in-crowd" lies a painful sense of inadequacy that seeps out gradually over the series. Established early on as an outsider, Dan is constantly worrying about whether or not he measures up to the kids at his elite private school. He complains about the Ivy League admissions process, which he believes is rigged against him since he's not a "legacy," but still dreams of attending one of the eight schools. His relationship with his peers is similar — when he feels rejected, instead of ignoring those who don't accept him, he tries to find a way to win them over.

While much of this is only visible in hindsight, his relationship with Serena is borderline abusive — his insecurities cause him to lash out at her verbally whenever he feels slighted by her. This is apparent from the second episode of the first season, when he can't handle the fact that Serena slept with Nate, or when he ends up sleeping with his teacher despite chastising Serena for doing the same thing. His hypocrisy truly knows no bounds. He ultimately ends up writing a novel completely trashing thinly-veiled characters from his life, including Serena (or "Sabrina" as he not-so-cleverly names her).

The decision to reveal Dan as Gossip Girl was the nail in the coffin for his post-show reputation, but now that HBO is rebooting the series (via Deadline), perhaps Dan's character will fare better.