Top 10 Cutest Gossip Girl Couples

Although their romance was short-lived, these two made an endearing and often underrated couple. Nate and Jenny became friends early on, and they were unlike any other characters on the show. Even the best friends on the series turned on and manipulated each other, but Nate and Jenny's friendship started out being much purer. When the world seemed crazy, they often turned to each other, and that’s what sparked their relationship. It's a shame that Jenny’s character changed so dramatically so quickly and they never got a real shot.

After seasons of them constantly at each other's’ throats, Dan and Blair getting together may have seemed a little weird, but it actually kind of made sense. While many couples on the show are born when characters give in to moments of physical temptation, Dan and Blair were very different. With their usual friends occupied, Blair and Dan are forced to bond having no other options. But the more time they spend together, the more they genuinely grow to care about each other. Having never really taken the time to get to know each other before, it was nice to see them actually develop a relationship and discover things they had in common.

Unlike with Dan and Blair, we didn’t see the friendship between Dan and Vanessa first bloom, since they were already besties when the show started. But we did witness a lot of sexual tension building up between them. Admittedly, it’s pretty awkward that they initially hooked up in a threesome orchestrated by Dan’s girlfriend-at-the-time, but out of that awkwardness emerged a love for the ages. They already knew they had a lot in common, and they made a cute little family raising Milo together, who Dan initially thought was his son. Also, it’s thanks to Vanessa that Dan’s novel got published.

Serena and Nate hooking up was the drama that started it all on this show. It launched several other hook-ups, and break ups, and threw a huge wrench into the lives of the young socialites. But things eventually simmered down and the two were great friends. It was only inevitable though, that all the lingering sexual tension there would eventually draw them into a serious relationship. It was super fun to watch the fulfillment of this childhood crush, but naturally, with Serena, the Queen of drama, it couldn’t last.

Many of the couples on this show fall prey to the uptown/downtown trope, where they didn’t work out because being from different worlds creates too much drama. But Nate and Vanessa were so low key it never really affected them the way it did the others. It wouldn’t be Gossip Girl if some drama didn’t come for them though. They still went through a handful of break ups and make ups, but for the most part they were just really chill, which is exactly what made them so fun to watch.

Their love was just so pure. Despite being secondary characters, we still got glimpses of their love blooming throughout the course of the show. We watched them get engaged, get married, and have children. Theirs is arguably the most stable relationship on the show. While all of the kids were busy hooking up, cheating on each other, generally going wild, and indulging in lost weekends, Dorota and Vanya were there in the background setting an example for the type of love we should all strive for.

They were high school sweethearts who grew apart as they got older, but always still had feelings for each other. When Serena and Dan broke up, they finally got a second chance at their first love, and even got married. It always seemed like a bit of a cop out that they broke up just because they came from different social worlds. It’s probably safe to assume that the real reason the relationship had to end was so that Dan and Serena still had a chance, but it could have easily been Rufus and Lily that ended up together instead.

Blair’s mom and stepfather met later in life, but they were just as passionate as teenagers, just without all the angst and drama. Cyrus' level of optimism felt really out of place at first because of how dramatic the tone of the show usually is, but he added such a bright spot, and was such a great match for Blair's cynical mom. They truly brought out the best in each other, and livened up every scene they were in together. If you ask us, we got “not enough!” of these two.

They’re the ship that started it all. S and Lonely Boy are the main couple of the show with their on again off again romance that spans the entire series. Defying the odds of their drama-fated lives, they spent the whole first season together in a pretty spectacular whirlwind romance that could make any teenager envious. And though they drifted apart and both found love with other people in subsequent seasons, they always managed to remain good friends and keep finding their way back to each other.

Before we unveil our top pick, here are a few honorable mentions:

Blair & Nate

Eric & Jonathan

Serena & Carter

Serena and Dan may be the couple we cheer for, but Chuck and Blair are definitely the most compelling, in a messed up kind of way. All of their crazy ups and downs are super fun to watch. Let’s be real, Chuck could be abusive and predatory, and we’re not praising either of them as role models. But, ironically, in some ways at least, the two are actually perfect for each other. They're both so manipulative and maniacal that the only thing better than the two of them clashing at the beginning of the series was them combining forces.