Gossip Girl Boyfriends Ranked From Pretty Bad To Even Worse

They say a good man is hard to find. Never has that saying been truer than on one of The CW’s most popular teen dramas, Gossip Girl. This really was a case of finding love in all the wrong places. We’re talking about being essentially sold for a hotel, teacher-student relationships, a dicey case of incest, and very ill-advised trysts with married men. Now we’re not saying that some of these guys simply don’t have any redeeming qualities but finding them would be a bit of a stretch. Our sincere condolences to Serena, Blair, Jenny, Vanessa and the others who were sacrificed so that we could have this list.

15. Colin Forrester

When we’re first introduced to Colin, we find him escorting a different woman into a taxi cab every morning. After establishing a rapport with Serena, an attraction clearly develops. That is until they realize that she is a student in his business class at Columbia. Despite a pact to remain just friends until they can fully explore their feelings at the end of the semester, the two give into the lust. Unfortunately, his meddling cousin Juliet is intent on exposing them to the dean as part of her revenge plot. Colin gallantly quits, but they couldn’t quite get past the family drama. Quite frankly, Serena was a flower that never should have been hidden even for a second. While a professor dating his student is definitely skeezy, what the others on this list have done is so bad, he got the best-of-the-worst title.

14. Steven Spence

When Serena disappeared for a spell, you almost hoped that she had finally decided to get away from her toxic dating pool for a while and focus on being fab all on her own. Instead, we found her masquerading as Sabrina from Wisconsin and shacking up with much older vitamin company CEO Spence. This relationship did bring out a certain maturity in Serena, but there was way too much going on. First of all, Steven had a teenage daughter who dated Nate and hated Serena with the fire of seven suns. But the real deal breaker was finding out that Steven had a past romance with mama Van der Woodsen. Um… no, thank you.

13. Aaron Rose

It started out innocently enough. Aaron was the adorkable Cyrus’s son, making him Blair Waldorf’s step-brother. When we learn he and Serena met as kids at Camp Suisse and had gotten “married” with licorice rings, it was awww-worthy. But then there was his whole open relationship thing, where he basically told her he liked dating multiple people at a time. That’s cool if that’s your vibe, but it clearly wasn’t Serena’s. He agreed to commit, but it just seemed like they were never really on the same page. Aaron was wary of Dan’s presence in Serena’s life, and she was forced to deal with Aaron’s ex Lexi when she sauntered into town. You could almost hear the universe’s collective sigh of relief when Serena returned from their Buenos Aires trip sans Aaron.

12. Lord Marcus Beaton

Initially we thought Lord Marcus Beaton was about to be just another pawn in Blair’s love game with Chuck. Little did we know that the Queen B was about to be played, herself. See, it turned out that Beaton was very close to his step-mother Catherine. A little too close, if you know what we mean. To make bad matters worse, Catherine also happened to be having an affair with Blair’s ex Nate. Her dreams of becoming royalty extinguished, Blair used photographic evidence of Marcus and Catherine’s betrayal to help Nate out of a jam. Sounds like a therapy sesh is desperately needed.

11. Asher Hornsby

About the only good thing Asher ever did was own cute dogs. Not much to write home about otherwise. Let’s start with the fact that he dated little Jenny Humphrey despite knowing that he was gay. And when Dan confronted Hornsby after witnessing a kiss between him and a mystery guy, he actually threatened to take his sister’s virginity. … What?! Then there was the time Jenny tried to take their relationship to the next level. Asher offered to play the doting BF, only if she continued to act as his beard. Luckily he’s exposed for the fraud that he is before doing further damage to Jenny or his mystery boo, Eric Van der Woodson. Good riddance!

10. Damien Dalgaard

The dashing son of the Belgian Ambassador also happened to be moonlighting as a drug dealer. And because misery often loves company, he recruited Jenny Humphrey to be his mule and tried to pressure her into having sex at every turn. But those weren’t Dalgaard’s only bad deeds. He was the one who started the rumor about Serena and her English teacher Ben Donovan, which sent an innocent man to prison. And if that wasn’t enough, he delivered primo blackmail info about Lily Van der Woodsen to sworn Bass enemy Russell Thorpe. What a guy.

9. Ben Donovan

It’s hard to not feel a bit sorry for Ben Donovan. The poor guy was Serena Van Der Woodsen’s English teacher at The Knightley School. He wound up being falsely accused of statutory rape after Damien Dalgaard started a rumor about the exact nature of their relationship. So you get why Ben would be a bit pissed about sitting in prison for something he didn’t do. You can even understand hatching a plan with his sister Juliet to destroy Serena. But then you date her after your release from prison, knowing that she was recently hooking up with your cousin Colin? WTF dude!

8. Gabriel Edwards

Serena sure knows how to pick ‘em. When we first meet Gabriel, he happens to be the boyfriend of Serena’s pal Poppy Lifton. The word “pal” is being used very loosely here. After an ill-advised trip to Spain, we learn that Serena and Gabriel hooked up and may or may not have gotten hitched. The two then decide to pursue an actual relationship. That blows up after it is revealed that good old Gabe and Poppy are not only still a thing, but happen to be conning Serena’s friends and family out of a ton of money.

7. Carter Baizen

Carter Baizen was bad news from the minute he stole Chuck’s prized baseball and swindled Nate at a poker game. Then he engaged in a fling with a vulnerable Blair before leading Serena on a search for her long-lost father. That act of good faith could have brought Carter back into our good graces. Instead, we found out that he asked an unsuspecting wealthy young woman to marry him so that could pay off his gambling debt. Mercifully, he left her hanging at the altar. The final nail in the coffin was when he pretended to have vital info about Serena’s dad just to try to worm his way back into her life. Boy, bye.

6. Nate Archibald

It’s easy to get sucked into Nate’s loveable stoner vibe but don’t get it twisted. Even he was as messed up as they come. Our dear Nathaniel was in a committed relationship with high school sweetheart Blair, but that didn’t stop him from sleeping with her best friend Serena at the infamous Sheppard wedding. Then he compounded matters by pining after S like a lovesick puppy when she returned from boarding school. Did we mention he was still Blair’s boyfriend at this point? That was enough to land him in the hall of shame, but honorable mention goes out to having a relationship with the underage Sage Spence and sleeping with a married woman to save his family finances.

5. Tripp Vanderbilt

This is one of these times keeping it in the family was not the best idea. Serena should have left well enough alone with Nate’s cousin Tripp, especially since he was married. There was also tension between the cousins as they fought for the affections of their grandfather. So the addition of the Upper East Side it-girl added more fuel to the fire. But where Tripp really proved to be the biggest loser was when he put an unconscious Serena’s body into the driver’s seat, after they got into a wreck, to cover his own ass. This politician lost our vote.

4. Louis Grimaldi

Louis may have had a royal title, but he was certainly no prince. After going to great lengths to marry Blair, like paying Chuck’s therapist to trigger a reaction which would drive B away, Louis informed his new wife that he no longer loved her. Instead, he was basically holding her hostage to a marriage contract. For someone who claimed to not trust Blair’s friends and their penchant for scheming, he sure had no problem getting in on the devious shenanigans. We’re more than happy Louis and his tarnished crown never returned to the UES.

3. Jack Bass

It makes perfect sense that Jack Bass’s best relationship was with the equally devious Georgina Sparks. As we all know, the couple that plots together stays together. But before the dastardly duo discovered domestic bliss, Jack Bass spent most of his days scheming against his nephew Chuck and had little regard for those who got in his way. That included attempting to rape Lily after she thwarted his attempt to retain control of Bass industries. And never forget sleeping with an extremely reluctant Blair in a deal to return the Empire Hotel to Chuck. He and Georgina deserve each other, tbh.

2. Chuck Bass

There was something about Chuck that always made him seem kind of predatory. Maybe it was the way he was always skulking in corners, his perpetually whispery voice, or his penchant for rooftops. It also didn’t help that he tried to forcibly kiss Serena and attempted to rape Jenny. Even though his unexpected relationship with Blair was based on their shared love of manipulation, they looked like a match made in meddling heaven. His violent acts made redemption not an option, but it was also absolutely unforgivable to have your girlfriend used as an unwitting piece in a ploy to get your hotel back. Especially when that involves having her sleep with your uncle.

1. Dan Humphrey

Dan Humphrey really had us fooled with his ‘Lonely Boy’ schtick, his earnestness, and moral compass. Lest we forget, this is the guy that ended things with his eternal crush, Serena, when he found out about the dalliance between her and Nate at the Sheppard wedding, among other indiscretions. Their worlds were so different, and he just couldn’t be part of this manipulative melodrama. So color us f&*#ing shocked when Gossip Girl turns out to be none other than one Mr. Daniel Humphrey. The very Gossip Girl who hung all Serena’s, Blair’s, Vanessa’s, and essentially anyone he’s ever dated’s dirty laundry out to dry. When you throw in the fact that Dan essentially put his little sister’s sexual history out on display as GG too, you sir, are officially the WORST!

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