The worlds of Moordale and the Upper East Side of New York couldn't be more different. The former, with its eighties vibe and distinctive countryside appearance, instantly clashes with the latter's luxurious, privileged and cosmopolitan environment. At first sight, it might seem like these would be the last two places to ever collide, in any way, shape, or form.

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Upon closer inspection, however, it becomes clear that several of the characters that inhabit each world share many similarities between them. Furthermore, they could actually form some really nice pairings, given the chance. And while some definitely clash against one another, creating a truly toxic dynamic, others would fit together quite nicely, bringing out the best in each other.

Wouldn't Work: Serena & Otis

Poor Otis doesn't have a chance with Serena. Shy and sweet, he might seem like everything she's looking for, after so many years of dating creeps and jocks. And he just jumps at the chance to date the most popular and beautiful girl in all the Upper East Side.

After a while, however, Serena's antics would prove too much for Otis to handle, and he would simply be unable to keep up with her. Because even at her best behavior, Serena is still too wild and unpredictable for such a vanilla boy. The two could remain close, though, fostering a connection that is better suited for a nice friendship.

Would Work: Eric & Rahim

Eric was always one of the most mature characters in Gossip Girl. Kind and supportive, he lives his life without getting too involved in the wicked games his sibling and friends enjoy playing, which makes him kind of an outsider in his world. He would be immediately drawn to Rahim, the romantic French transfer student, and the two would quickly form a strong bond.

The confident and suave Rahim makes a perfect match for the sweet, understanding Eric. They're both comfortable with their sexualities and identities to create a real connection, and they could easily bring something to the relationship without ever sacrificing their individuality.

Wouldn't Work: Lily & Dan

Dan is the type of guy that would try to understand Lily, and she's a really interesting and unexpected girl, even if she does have more than a few bizarre quirks. Their relationship would most likely be mocked by the unforgiving and judgemental eyes of the Constance/St. Jude's crowd.

However, Dan's "nice guy" persona would emerge, and he would attempt to change Lily's behavior, trying to make her less quirky and more conventional. But Lily is not willing to change, for him or anyone else. Dan's wounded pride wouldn't even allow for a friendship.

Would Work: Jenny & Jackson

Jackson Marchetti is everything Jenny Humphrey wants. He's handsome, athletic, rich, and popular beyond belief. To top it all off, he's a genuinely nice guy who really works on his relationships, a romantic who's not afraid to make a grand gesture.

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Jenny would easily fall head over heels for him. Jackson would appreciate how spirited and ambitious she is. Jenny would help Jackson explore all his possibilities outside of swimming. For his part, he could support her, preventing her from falling under the toxic influence of Constance's mean girls, and instead encouraging her to focus on her fashion career.

Wouldn't Work: Lily & Remi

Two appetites can't satisfy each other, which is why Lily van der Woodsen and Remi Milburn would never work. They could actually get married, though, as he is exactly the type of man Lily usually falls for, and stay together for some time, creating some happy memories together.

But they'd both get tired of each other. Rami would sleep around because that's what a selfish man like him does. Lily would become distant and start weighing her options. These two would end up divorcing, although they'd always care for each other.

Would Work: Jean & Rufus

Renowned sex therapist Jean Milburn has a primal side that she's not afraid to explore, or indulge. Rock star turned gallery owner Rufus Humphrey seems safe and reliable, but he too has a wild persona just waiting to be released.

Together, they would bring out the best in each other. He wouldn't force insecurities about her success and would encourage her every step of the way. She too would push him to aim higher, always giving him enough space to be his own man. Jean's bold and direct approach could prove a bit intimidating for Rufus' children, but they'd eventually warm up to her. On the contrary, Otis would immediately take a liking to Rufus.

Wouldn't Work: Ola & Nate

Nate would like how liberated she is, standing in stark contrast to the prim and proper girls of Constance. She would be struck by his handsome looks and laid-back persona enough to give him a chance and explore the possibility of a relationship.

But Nate is just boring for her, while he'd be intimidated by her personality. Nate and Ola would probably make great friends instead of romantic partners.

Would Work: Eric & Jonathan

Eric Effiong is brave and daring, unafraid to put himself out there and show the world who he really is. He needs someone who'll love and accept him for who he is, someone who'll hold his hand without worrying about what the rest of the world will think or say.

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Jonathan Whitney is by far, the best boyfriend in Gossip Girl. Sweet, supportive, understanding, and unproblematic, he is the ideal guy for Eric. The two would have a stable and almost perfect relationship, filled with laughter and love, one that not even Gossip Girl can bring herself to destroy.

Wouldn't Work: Aimee & Chuck

Chuck Bass is not the best of the characters, especially in high school. Manipulative, selfish, controlling, scheming, and cruel, he's an overall bad person who enjoys playing games with others. Aimee might be innocent and unassuming, but she's neither dumb nor weak.

She might give him a chance, but almost immediately she'd regret it. Nearly everyone can see how little sense they make together, including the two of them.

Would Work: Blair & Maeve

Blair was always ambitious and inspiring. She wanted the world because she knew she deserved it and wasn't afraid to go after her dreams. A romantic at heart, she longed for and deserved a great love story. For her part, Maeve is someone life forced to grow-up sooner than expected. Staunchly independent, she's been looking after herself for a while, which makes her wary of trusting others.

Together, these two could rule the world. They're both incredibly intelligent and resourceful, willing to go to great lengths to achieve their dreams. Maeve would encourage Blair's softer side, preventing her from indulging in her scheming and petty impulses. In return, Blair would help Maeve open up and embrace life and romance. They each would make the other stronger and happier, and the two would finally find love where they least expected it.

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