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.