Things you buy through our links may earn Vox Media a commission. There comes a point in the lifespan of a soap opera when the sexual interactions between characters reach a tipping point — or, the ideal conditions for contagious diseases — and almost everyone has slept with almost everyone else. After four seasons of , Kelly had slept with Steve, Brandon, and Dylan. On Gossip Girl , which thankfully returned last night , the bed-hopping is the most intense of all. This email will be used to sign into all New York sites. By submitting your email, you agree to our Terms and Privacy Policy and to receive email correspondence from us. Account Profile. Sign Out. Chuck tried to rape Jenny in the pilot. Two seasons later, feeling low, he took her virginity. S2 Chuck and Blair , Gossip Girl 's super-couple. S Jenny has crushed on Nate with increasing ferocity, but it's never progressed past kisses, which Nate usually intends for Serena anyway. S Serena and Lonely Boy have been on and off and on and off and on and off and on and off, and on and on and on and on. S Blair and Nate were the high school golden couple, but never had the same passion for one another they reserved for Chuck and Serena, respectively.
https://cdn.justjared.com/wp-content/uploads/headlines/2022/12/gossip-girl-update-on-dan-serena.jpgA definitive ranking of every shitty boyfriend Serena ran through on Gossip Girl
S3 Nate lost his virginity to Serena before the show began, but it took the pair two seasons make it temporarily official. S Vanessa and Nate had a sweet Manhattan-Brooklyn romance, before the writers decided it was time Blair got Nate back. S1,2 This Asian chick couldn't get a lovelorn Chuck to, ahem, rise to occasion. S4 How many girls does it take to forget Blair Waldorf? Sadly for Chuck, more than three topless ones on a Hamptons beach. S2 After sleeping with Elle at an Eyes Wide Shut sex party he barely remembered, Chuck fleetingly became convinced she was the one. S2 Mourning his father, Chuck took solace in two hookers. S2 Owing to Blair's manipulation, Chuck kissed Josh Ellis —by his own admission, not the only dude he's smooched. S2 If Chuck couldn't have Blair, who broke up with him after he tried to pimp her out to his uncle, he'd have this random chick. S1 Chuck tried to get over some Blair-caused erectile dysfunction with this young lady , to no avail. S2 Fresh off almost raping Jenny Humphrey in the pilot, Chuck recovered by shagging two of his father's hotel employees.S3 Georgina Sparks probably gave Dan a blow job all the way back in season 1. Two years later, after some casual screwing, they have a son maybe. S1, 3 When Dan got hot for teacher, that teacher was Ms. S2 In the summer between season's one and two, Dan hung around with Jeremiah Harris and slutted it up with lit-girls like this. S2 Blair accused Serena of smooching Cristiano Ronaldo over summer vacation, and we believe her. S3 Aaron Rose was a wispy bearded artist with monogamy issues, so, of course, it took Serena multiple episodes to realize he was the worst. S2 When Serena said "I killed someone," she was talking about Peter , whom she hooked up with on a hidden camera before he OD'd. S2 Nate seriously dated familial enemy Bree Buckley , until he realized she's only with him to get revenge on Carter Baizen. S3 With the help of Chuck's little black book, Nate had quite a summer. This girl at least got treated to brunch, too. While at Yale, Nate sampled the goods in the form of one Jordan Steele. S2 Nate's strategy for getting over Serena: lots of loose women. Later, she almost prostituted herself to him on Chuck's behalf. S2,3 On a dare from Jenny Humphrey, Blair made out with a random dude at a bar. S1 Eric and his largely drama-free boyfriend Jonathan dated until Eric's Jenny-rage caused them to break up. S2,3 Eric's most recent fella, Elliot , is, dangerously, a bisexual. S3 Asher Hornsby secretly dated Eric before publicly dating Jenny. In the immortal words of Gossip Girl: "Don't look so sad, little J! The sun will come out tomorrow, even though your boyfriend did today. A later relationship bloomed a few years after he was Blair's self-destructive bad habit S1, S3 As a new college Freshman, Dan landed himself movie-star girlfriend Olivia Burke.
The Ultimate Ranking of Serena's Hottest Boyfriends on Gossip Girl
The pair broke up after a threesome with Vanessa made Dan realize his heart belonged to V. Tags: gossip girl tv bed-hopping. Most Viewed Stories. By submitting your email, you agree to our Terms and Privacy Notice and to receive email correspondence from us. Already a subscriber? Sign In. What is your email? Enter your email: Please enter a valid email address. Submit Email. Connect with Google Connect with Facebook. Sign in. Choose a password to create an account: Enter your password or sign in with a different email Forgot Password? This password will be used to sign into all New York sites. Sign In Create Account. I am not slut-shaming Serena van der Woodsen. If a gal wants to ditch her panties at 1OAK, sex up married politicians in the back of a cab, or have a pregnancy scare with more baby daddy possibilities than she can count on one hand, that's fine! I'm pretty sure that's what Ruth Bader Ginsburg fought for, according to the trailer of her surely-straight-to-DVD biopic I accidentally watched on Twitter! But what I will do is love-shame Serena van der Woodsen.As I started power-ranking every rich dude she let hit it throughout the Greatest Show of Our Time , I noticed a pattern: she really thought she loved all of these guys! And that's the truly batshit insane thing about SVDW. And by the end of this list, I think you will too. Over the course of I think two episodes, Serena emotionally sluts it up so hard it makes a Bachelor contestant look like she's in it for the right reasons. Armie plays Gabriel Edwards, a southern businessman who she first met while he was dating her good friend, Poppy Lifton. So despite him being the serious boyfriend of one of her best friends , Serena gets so swept up in his Tall White Manliness that she "marries" him on vacation. He then proceeds to scam millions from her mom, her ex's dad, and virtually everyone who lives in her building. Who among us hasn't been hypnotized by beautiful, generic symmetry? I'll give her this one. He didn't even attempt an accent. Though I've basically got Us Weekly for brains, I'm having a very hard time recalling a single Nate plotpoint that didn't involve him fucking an older woman for money. I know Blair and Serena were both trapped in revolving-door relationships with him but…what happened in them? What did Nate do at all???? There was him sleeping with Duchess Catherine for money who's Betty's mom on Riverdale, can you believe?! Then he became the mayor, I guess. Everything in between is a blur, especially anything involving Serena — any time their boring blondness synched up, I would fast-forward through their scenes. It's because of this aggressive non-descriptiveness that Nate ranks towards the bottom. I would have put him dead last, but my boyfriend told me he once met Chace Crawford at a wedding in Texas and he was lovely.
Timeline of Gossip Girl
Why didn't they release it as a series tie-in? Sure, he tried to kill Serena because her mother got him falsely convicted of raping her! Sure , he always sounds like he's growling and sure , he's got the blank, liquid gaze of someone on a mood stabilizer. But that didn't stop Serena from diving into her most ill-advised relationship with her former boarding school teacher, freshly out of jail for her statutory rape. Maybe Ben wasn't directly involved in Vanessa, Jenny and Juliette's plan to drug Serena and leave her for dead beneath and overpass, but he did put all the pieces into place. And for that, I say thank you because it was by far the best of the absolutely bonkers late-season storylines. It's so sad and sweet and cute and Ben is played by kind of an amazing actor. Serena doesn't know how to read, duh. Tag yourself, I'm the simple yet effective screen name 'N8'. So he and Serena never actually dated for real, but he was her date to the Kiss on the Lips party while Dan was too busy being literate with Vanessa in his garage-room. And he twirled her around a bunch. Which is really all a girl could ever want on the dancefloor. Even in , I thought that ship had sailed. The first man to leave Serena for dead in a hospital bed! What a novel thrill that was. Remember when she had the fucking nerve to show up at Thanksgiving with him wearing that skin-tight lace catsuit and have a stare-down with his wife and Lily was like "Serena, you're not welcome in my home while you date a married man of an indecipherable age! There are so many things I can't relate to about Gossip Girl: being that rich, being that beautiful, managing to bend time and space so I can get lunch at my loft in Williamsburg and be back to school on the UES within an hour. But we all relate to the Aaron Fucking Rose storyline. Who among us hasn't unwittingly entered a love trapezoid with a dirty RISD dropout and his bevy of Instagram-ready beauties, only for him to drop us lines like "I'm not going to explain who that girl was, I thought you were more mature than needing a label for this"? While Aaron never did anything especially insidious, he's just such a prototypical shitbag that I'm angry he ever dared darken Serena's condo's doorstep.
Or elevator step, as is the case with the Bass-Van der Woodsen compound. I have to be honest with you, dear reader s. I remember…next to nothing about Steven Spence and his arc. I remember his Serena-aged daughter was yet another one of Nate's inappropriate love interests, and I remember Serena lied to him and said she was from Wisconsin. A quick Wikipedia sesh reveals that Steven and Lily hooked up in their youth! And the worst part? That wasn't even enough to keep Serena away. I used to be an editor at a society magazine so to this far-fetched subplot, I'm uniquely qualified to say looool no. Again, not a proper boyfriend but he was part of such a glorious episode that it would be a crime to leave him out. You know the episode, it was series defining — Dan goes on a date with Amanda played by Vanderpump Rules loser Laura Leigh!!!!!!!!! To which I say: wig! He's a billionaire. And a businessman. And a best-selling author. And a guest lecturer at Columbia.
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