Chuck Bass pretty much ended up as the most iconic character from Gossip Girl. His laid-back, cool-guy persona has been imitated in various other shows since, and the development of his character from an arrogant womanizer to a man simply overwhelmed with love for Blair Waldorf is truly one of the show’s strongest points.
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In the books that inspired the show, he was a much more minor character but still flitted between women like it took no effort whatsoever. We’ve gathered ten people Chuck could have ended up with if Blair ever changed her mind about him.
10 Eva Coupeau
Arguably the only character in the show that Chuck ever showed any real, genuine and deep affection for aside from Blair was Eva Coupeau. Portrayed by Clemence Poesy (known for playing Fleur in Harry Potter), the mysterious French girl seemed to be one of the only truly kind characters in the show. She ended up turning him into a charitable, kind man for a while, before Blair set them up, mislead Chuck and he broke up with her.
When he realized this was all a lie, it was too late and she was gone forever.
9 Raina Thorpe
One of the only girls Chuck was able to actually call a true girlfriend other than Blair was only in Gossip Girl for a brief period. The daughter of Russel Thorpe, the two enter a confusing relationship while her father attempts to kill about ten people at once, after having previously revealed to have killed Raina’s daughter.
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She ends up hating her father and remaining friends with Chuck and Nate, but returns to Chicago and doesn’t appear in Gossip Girl again.
8 Jenny Humphrey
Jenny and Chuck got off to a really, really bad start. It was, of course, Chuck’s fault in every single conceivable way as he pursued the fourteen year and old and literally attempted to rape her.
It’s sort of unforgivable, but if there is one character we know can change, it’s Chuck Bass. In Jenny’s final days on the Upper East Side, she ended up losing her virginity to Chuck, much to the dismay of Blair Waldorf. Despite this, the two actually work quite well as a team and, even if he doesn’t exactly sleep with her for the right reasons, they do seem to provide each other with some comfort.
7 Georgina Sparks
Georgina Sparks is a very strange character. All of the puzzle pieces fit together and seem to suggest that she was Gossip Girl this whole time, but she pretty much ended up as a character who just absolutely loved creating and being near as much drama as she could find.
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Chuck lost his virginity to her long before the events of the show, and even though they often didn’t see eye to eye afterward, or even have that much contact, it would have been quite nice to see their young love blossom one day.
6 Alessandra Steele
In season five, we are introduced to Alessandra Steele. She is a publicist, working with Dan, taking a very interesting approach to publicity regarding his novel, Inside. Chuck, again, not working under the best intentions, ends up hooking up with Alessandra as a way of getting back at Dan for being with Blair.
The two, obviously, don’t work out, but there did seem to be an element of mutual respect there that might have worked out differently in different circumstances.
5 Vanessa Abrams
A lot of time is spent in Gossip Girl with Vanessa absolutely hating Chuck, and Chuck pretty much returning the very same feelings. However, there is the occasional moment that makes you think about the two slightly differently. Firstly, when Chuck buys the bar Vanessa cares so much about, their relationship changes slightly.
He realizes she isn’t so bad, and she realizes he isn’t so cruel. Of course, in true Chuck fashion, they end up sleeping together as a way of Chuck getting back at Blair, but there could have been something else there at some point along the way…
4 Serena Van Der Woodsen
Now, this one is a bit weird if you think about it from the perspective of after season six. By this point, Lily has adopted Chuck and he and Serena are legally siblings. Obviously, this would be a bit weird.
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However, earlier on in the show, it is shown that the two genuinely care for each other deep down, no matter how many times they suggest otherwise. Chuck spends half of his time in the early seasons being rejected by Serena, and who knows whether his interests were purely sexual or not, but the two-match rather well in personality in a lot of ways.
3 Nate Archibald
In the Gossip Girl books, it is very strongly suggested that Chuck is at the very least bisexual, and he tries to be gay a fair few times. For some reason, they pretty much cut this entire trait from the show.
However, if there was one way they were ever going to bring it back, it would be through the power of the Chuck and Nate bromance.
2 Josh Ellis
Speaking of Chuck’s bisexual traits, the one very small slither of a hint of a possibility of an inkling of this the show comes from his kiss with Josh Ellis. It might be mostly set up, but under different circumstances, who knows what that kiss could have led to.
After all, he does ask Blair straight after, “Do you really think I’ve never kissed a guy before?”.
1 Or… Just Stick With Blair
Despite all of these possible matches for Chuck Bass, there is one thing that connects pretty much every single one of them. They’re almost all desperate attempts to either make Blair jealous or notice him.
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This basically confirms what Gossip Girl showed us all those years ago: Blair and Chuck were always meant to be together. They only truly cared about each other and were only going to end up together. This means we can ignore all of these fictional partners and focus on what we actually got.
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