Gossip Girl: 10 Best Couples & Their Most Iconic Scene

There were a few iconic Gossip Girl couples that left an indelible mark in fans’ hearts, and some that were fleeting but still full of great scenes.

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The king of teen dramas may have primarily been about rich people being awful to each other, but fans would agree that Gossip Girl also had its foundation firmly laid in romance. The writers loved love, and sparks flew between Serena, Nate, Blair, Chuck, Dan, Vanessa, and many others outside their bubble in almost every episode.

There were some iconic couples on the show that left an indelible mark in fans’ hearts, and some others that were fleeting but are worth mentioning because of the great moments they shared with each other.

Serena & Dan: A Snowy Christmas

The two star-crossed lovers were adorable when they first met and started dating in season 1 (even though they had met before and only Dan remembered). The beginning of their relationship was full of firsts, and their first Christmas together was enchanting. With Vanessa’s help, Serena set up the perfect snowy Christmas for Dan in the art gallery, replete with projections of snowy landscapes on the walls and a cozy nest for the two of them in the middle of it all.

It was a testament to how much Serena loved Dan that she set something artistic up for him, rather than buying him a generic present. In this scene, Dan told Serena about his first brush with her on October 8th many years ago, and how he wrote a short story about that night. They then had sex for the first time, which was a big milestone for their relationship.

Dan & Blair: The Princess Of The Met Steps

Dan and Blair’s relationship was full of cute moments and the best quotes. The two of them were one of the few healthy relationships on Gossip Girl, and Dan picked up a broken Blair and put together the pieces when she was at her lowest, first as a friend and then as a lover.

After a harrowing and short-lived marriage to Louis, Blair felt like a shell of her past self. To make Blair feel like a princess again, Dan dressed her up, bought her a fake tiara, and took her to the Met steps, a place she once ruled while at Constance Billard. Young girls from the school crowded around her for selfies and compliments, which helped rebuild Blair’s confidence. It was a really selfless and romantic gesture on Dan’s part and showed that he really cared for her.

Blair & Chuck: Victrola And The Limousine

Much to GG fans’ delight, Chuck and Blair were true soulmates and ended up together at the end of the show in a hurried but romantic ceremony. But looking at their complicated relationship, one can only think back to how it all started in a burlesque club one fated night.

After a bad breakup with Nate, she ended up at Chuck’s club, Victrola, and something made her shed her inhibitions and do a dance for him, which really captured Chuck’s attention. In true Upper East Side style, they ended up back in a limo, and after asking her if she was sure, they got together, which marked the beginning of a legendary romance.

Dan & Vanessa: The Kiss At The College Party

When Dan’s best friend Vanessa finally showed up in Manhattan, many thought that they must harbor secret feelings for each other, but the two only got together in season 3 of the show. When Dan realized he may be in love with Vanessa, he didn’t show it, but the beach party at their NYU dorm brought it all out.

After a messy threesome, Vanessa and Dan skirted around each other until the tension between them was too much to handle and they ended up kissing passionately behind the photobooth at the party. This was their first meaningful kiss, and it was a relief to see them actually act on what they felt.

Chuck & Eva: We Don’t Need Tickets

Chuck didn’t have many love interests, but one of his few true relationships was the one he shared with Eva. He may have got together with Eva as Henry Prince, but the billionaire Bass had no intentions of leaving her behind when he returned to the Upper East Side.

His love for her really showed when he went back to being Chuck Bass in Paris, introduced himself to Eva, and told her that she should come to New York with him. When she asked him about tickets, he told her that they didn’t need tickets. Eva really transformed Chuck into a philanthropic, well-meaning man, and this was a pivotal point in their relationship.

Serena & Nate: The Night At The Campbell Apartment

The two most good-looking individuals of the Upper East Side had to end up together at some point, and Nate and Serena’s relationship was just like a Taylor Swift song — full of betrayal, secrecy, some happiness, and unresolved emotions on both ends.

They were attracted to each other while Nate was still dating Blair, so in an inevitable inebriated moment, the two of them hooked up during the Campbell apartment, which haunted Serena so much that she ran away from home. This hazy scene of teenage love was one of the most important plot points of the first season of Gossip Girl, and it set the tone for Serena and Nate’s relationship too.

Rufus & Lily: Meeting Their Son

In an instance where the parents’ storyline was better than the teens on Gossip Girl, Rufus and Lily had a romance for the books which spanned decades and had several spectacular moments throughout. It was heartwarming to see their enduring love for each other, and audiences really felt it on the day of their wedding.

After almost breaking up, the two decided to go all in, but the arrival of their estranged son who had been given up for adoption on the day ruined all plans of a big sparkly wedding. Instead, they reunited with their son, who was a beacon of their love for each other, and had a low key ceremony at the loft later.

Dorota & Vanya: The Proposal

They may not be main characters, but audiences loved Dorota, and especially liked the romance she had with Vanya, the doorman in the Van der Woodsen’s building. The two Russians had a shared culture, and their love for each other was as pure as it got on Gossip Girl.

When Dorota found out she was pregnant, she was upset because she was worried about her parents who may not have wanted her to have a child out of wedlock. The ever-so-caring Vanya decided to propose to her with a heartfelt speech in the building lobby as the gang played a game of Assassin on Nate’s birthday. Their excitement to begin a new life together was on full display in this moment.

Cyrus & Eleanor: The Wedding

Like Blair, Eleanor also found true love, albeit in the form of the stocky and easily excitable Cyrus Rose. Blair found fault in him initially because he wasn’t what she expected, but once she saw that he had pure intentions with her mother and how happy Eleanor was with him, even she couldn’t stay away from his infectious energy.

The couple had a beautiful and intimate wedding in the Waldorf home, with the presence of both their kids and closest friends. It was heartwarming to see Eleanor, who had had a tough marriage with Harold, finally get her happy ending with a supportive husband and father for her child.

Vanessa & Nate: The First Date

The first interaction between Vanessa and Nate had her believing that he was a stuck-up rich kid, but that quickly changed to instant chemistry and fondness between the two. Nate was very caring and Vanessa was pleasantly surprised by a man who knew Brooklyn as well as he did, considering his pedigree.

That first frosty interaction quickly turned into a first date where Nate and Vanessa ended up going for her sister’s concert together, and walked to the café where she worked. They had a cute “doorstep moment” where they shared their first kiss. Their interaction during this date cemented their relationship and its dynamic, which continued until they broke up.

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