No one ever had trouble finding a date on the Upper East Side. The lavish events and cocktail parties in Gossip Girl brought elites from all over the world to New York City. The main cast of the teen drama often mingled with each other, but there were some pairings that never became anything more than friends.

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Given how much the series likes to mix and match the characters, it's surprising that there are so many relationships that weren't taken advantage of. There was sizzling chemistry between the entire cast, and fans found themselves drawn to potential romances that were never explored.

Ivy And Georgina

Georgina and Ivy in Gossip Girl

Georgina was the only ally Ivy had after her true identity was revealed, causing Ivy to become rather dependent on her. Georgina isn't the sentimental type and she always looks out for herself before anyone else, but there were a few instances where it seemed that she cared about Ivy more than she let on.

That's not saying much, given that even when Georgina cares she doesn't care enough, but a relationship between her and Ivy could've helped Georgina's walls come down.

Blair And Jenny

Blair Waldorf with her arm around Jenny Humphrey in Gossip Girl

At the beginning of the series, Jenny looked up to Blair and saw her as a role model. She would do anything to be her friend, and Blair used the opportunity to take advantage of her. Eventually, Jenny decides to fight back against Blair and the two of them end up becoming rivals.

Rivals to lovers is a popular trope in fiction, so for that reason alone, a romance between Blair and Jenny would be worth exploring.

Vanessa And Olivia

Olivia and Vanessa in Gossip Girl.

Olivia might have been dating Dan, but she and Vanessa got along just as well. When Dan, Vanessa, and Oliva all decide to have a threesome to complete a checklist, things get awkward between them.

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The problem was that Dan appeared to be more into Vanessa than he was his girlfriend, but it would've been a better idea if the roles were switched up. Olivia and Vanessa's chemistry was off the charts, and it's hard to believe that they didn't end up feeling something for each other during the endeavor.

Chuck And Nate

Nate and Chuck in Gossip Girl

No matter how many horrible things Chuck did, Nate never gave up on him. There were multiple times when he should've turned on his best friend, as it's no secret that Chuck Bass belongs behind bars, but the fact that he didn't was proof of his loyalty.

Nate is one of the few people Chuck always wants in his corner. He's standoffish to almost everyone else, but his relationship with Nate is one of the best things about him. If Chuck dated him, it could've been his first healthy relationship.

Rufus And Dorota

Rufus and Dorota in Gossip Girl.

Rufus and Dorota aren't an obvious pairing, but that's mostly due to them rarely having scenes together. The fact of the matter is, is that if the two of them had more screentime, there probably would have been a great connection.

Rufus and Dorota both give their all to the people they care about, and unlike most of the characters on the Upper East Side, they had to work hard to make a living. There's no doubt that they would have an appreciation for each other that could easily become more.

Georgina And Blair

Blair and Georgina in Gossip Girl.

Out of all the characters in the series, Blair and Georgina were two of the most similar. Blair had more of a conscience than Georgina did, and she had the compassion that Georgina lacked, but everything else about them was alike.

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Blair and Georgina are both geniuses when it comes to planning schemes, and when they teamed up they were a force of nature. If they ever decided to date they would be the epitome of a power couple.

Nate And Dan

Dan and Nate stand side by side with school uniforms on in Gossip Girl.

Nate and Dan was an unexpected relationship, which is what made it so beloved by viewers. Most of the students at Constance either bullied Dan or acted like he didn't exist. Nate was one of the more pure characters out of the main cast, and he eventually ended up in Dan's corner.

Nate became one of Dan's closest friends, and he always stood up for him and his sister. A friendship as adored as this one would be a great foundation for a romance.

Vanessa And Serena

Vanessa and Serena in Gossip Girl.

Things were a bit awkward between Serena and Vanessa at first. Serena was dating Dan, and Vanessa had just returned to town to tell Dan that she had feelings for him. However, they connect instantly and Dan is impressed at how well they get along.

They have their ups and downs through the seasons, as all the characters do, but Serena and Vanessa could have been compatible. If they were willing to sit down and work out their issues, it would be a fun dynamic for the show to explore.

Ivy And Chuck

Ivy and Chuck in Gossip Girl.

Ivy and Chuck are both manipulative characters who think a lot alike. Although Ivy at her worst isn't as bad as Chuck at his, neither of them are great people. Chuck and Ivy didn't interact much and never became an official couple, which is odd given their potential.

All that Ivy wanted was for someone to care about her, and Chuck wanted someone who could accept him at his worst. There's no doubt that Ivy would be able to relate to him, and they could've been what one another needed.

Blair And Serena

Blair and Serena walking outside together on Gossip Girl

Blair and Serena are one of the most popular fan-ships and the friendship at the heart of Gossip Girl. Blair and Serena had been best friends for years until Serena betrays her and hooks up with Blair's boyfriend. Unable to face what she did to Blair, Serena flees town, leaving Blair confused and heartbroken.

There were a lot of issues for them to work through, but there was nothing that could ever stop them from loving each other. This kind of unconditional love could almost ensure that if Blair and Serena got together, it would be for life.

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