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6 Gossip Girl Boyfriends Ranked From Worst To Best



Although Gossip Girl has been cancelled for a few years now, it’s always satisfying to revisit this scandalous series and relive all the tantalizing drama. With the life of Gossip Girl surmounting to six total seasons, there was so many plot twists, surprises, climaxes, fallouts and reunions amongst the show’s characters. One ever-revolving door of attention-grabbing drama was the constant change in love interests amongst the female characters, mainly Blair Waldorf and Serena van der Woodsen. Serena and Blair’s male companions varied drastically throughout different episodes and seasons, ranging from good boys to mere boy toys to some real rotten apples—making their make ups, break ups, love triangles and emotional rollercoasters that much easier to obsess over. For a true guide to the show’s male love interests, here are 6 of Gossip Girl’s boyfriends ranked from worst to best.



Chuck Bass
Although his bad boy personality may win points with some fans as simply misunderstood, Chuck Bass was pretty much the handsome jerk who had his slightly endearing moments sprinkled throughout the series. Do those good moments outweigh the trouble and heartache he caused – like when he tried to physically assault Serena, not to mention his countless physical and verbally abusive encounters with his girlfriend Blair? Not on this list.



Tripp Vanderbilt
This guy ranks pretty low on the list for a few simple, but essential facts. Tripp was a full on adult trying to score with a mostly underage Serena, who was 16 years old during the height of his obsession with her. This is all while he is married. Yeah, not your best move, Tripp.


Gabriel Edwards
Any guy who is cheating throughout the duration of a relationship can’t get much praise. Albeit short lived, Gabriel dated Serena, all the while still dating his then supposed “ex” Poppy Lifton. Both Gabriel and Poppy were betraying Serena the entire time with an elaborate Ponzi scheme.




Dan Humphrey
One of the most mysterious characters on the show, Dan is ranked mid-way through the list because he eventually ends up with Serena, but also turned out to be pretty manipulative and crappy in a lot of ways. He reveals in the end that he was Gossip Girl the entire time, which means he was the voice of a lot of terrible, judgmental and all-around instigating commentary. But as an upper middle class Brooklynite, he also held his own in the cut-throat world of the Manhattan’s East Side, and did anything to be with his long-time crush Serena.


Carter Baizen
This guy had his faults, mainly gambling and a mountain of credit card debt, but he was probably one of the sweetest boyfriends Serena ever had throughout the series. He even helped Serena find her dad.



Nate Archibald
Even though this guy had some weird kinks, Nate was one of the most lovable characters on the show. He was the center of a love triangle with Blair and Serena, but he was generally good-hearted and tries to do the right thing in most situations. Not to mention, he only gets cuter with time.