The Definitive Gossip Girl Hookup Chart


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 90210, Kelly had slept with Steve, Brandon, and Dylan. By season three of Grey's Anatomy, George had slept with Meredith, Callie, and Izzie. On Gossip Girl, which thankfully returned last night, the bed-hopping is the most intense of all. Nate's slept with Blair, Vanessa, and Serena; Vanessa's slept with Nate, Dan, and Chuck; Serena's slept with Dan and Nate; and so on and so forth, and that's not even including all of the partners the gang has banged outside of their immediate social circle. So, as a way of saying welcome back — and we're looking forward to a season that includes just as much, if not more, fluid swapping than ever before! — we've documented all of the characters' hookups with one another, strangers, hookers, duchesses, liars, closet cases, politicians, and, of course, soul mates in this one pervy chart. (The "S" after each entry indicate which season(s) the dalliance occurred in.)

Chuck tried to rape Jenny in the pilot. Two seasons later, feeling low, he took her virginity. (S1, 3)
Trying to break up Nate and Blair, Chuck and Vanessa wound up doing the nasty instead. (S2)
Chuck and Blair, Gossip Girl's super-couple. (S1-3)
Jenny has crushed on Nate with increasing ferocity, but it's never progressed past kisses, which Nate usually intends for Serena anyway. (S1-3)
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. (S1-3)
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. (S1, S2)
Longtime BFFs Vanessa and Dan's inevitable relationship began, as these things are wont to do, with a ménage à trois. (S3)
Nate lost his virginity to Serena before the show began, but it took the pair two seasons make it (temporarily) official. (S1-3)
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. (203)
When Chuck got shot on the mean streets of Prague, Eva nursed him back to health. (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. (S3)
Though Chuck forsook college, he did not forsake the Princeton rep at the Ivy League mixer. (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. (S1)
At the end of season one, Chuck blew Blair off for Amelia (Lydia Hearst), using his best pick-up line on her: "I'm Chuck Bass." (S1)
Before she had Dan, Vanessa had his secret half-brother, Scott Rosson. (S3)
Vanessa dated Tisch-kid Paul Hoffman, while figuring out/ hiding from her feelings for Dan. (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. Carr. (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. (201)
Just a month after Bernie Madoff, Serena started sleeping with Gabriel Edwards, her own personal Ponzi schemer. (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. (S1)
Nate's married congressman cousin Tripp Van Der Bilt left his wife for Serena, before leaving Serena in a car wreck. (S3)
For one summer, Nate played cub/gigolo to cougar Lady Catherine Mason Beaton, a.k.a. the Duchess, a.k.a. a woman sleeping with her stepson. (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. (S3)
To make Chuck jealous, Blair dated Lord Marcus Beaton, who had a silly British accent and was sleeping with his stepmother. (S2)
Blair had a one-night stand with Jack Bass on New Year's Eve. 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)
Before turning to Chuck, Jenny tried to lose her v-card to douchebag drug dealer Damien Dalgaard. (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." (S1)
Serena and Carter Baizen have a history that started in Santorini. 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 pair broke up after a threesome with Vanessa made Dan realize his heart belonged to V. (S3)

Real life connections (solid line): ON OFF ONLY