Top 10 Gossip Girl Love Triangles

Talk about a royal affair! During season two, Blair discovers that her summer-fling turned boyfriend, Marcus, is actually a lord pretending to be an American college student. She subsequently devotes a lot of energy to impressing his haughty family, including his stepmother Duchess Catherine Beaton. Blair shouldn’t have wasted her time because it turns out, royals are no more well-behaved than our favorite upper east siders. In a surprising turn of events, Vanessa finds out that Marcus is hooking up with Catherine and understandably, Blair breaks up with him. Marcus was just Blair’s rebound from Chuck anyway...

Most viewers can agree that Dan and Blair were an unusual pairing. That’s why it only seemed natural for her to re-develop feelings for Chuck while she was still dating Lonely Boy. Dan and Blair’s relationship always felt more like a plot device than a true romance, and we could tell that her heart wasn’t fully in it. While Dan was a nice change of pace and gave Blair a sense of safety, he was proof that Blair could never love anyone the way she loved Chuck. Thankfully, after coming to her senses, Blair breaks up with Dan, and things on the Upper East Side return to normal.

For years, Dan was the shy Brooklyn boy who pined after “It Girl” Serena, but clearly, Dan had more luck with the ladies once he entered NYU. So much so that he managed to win the affections of both Olivia, the movie star, and Vanessa, his long time best friend. Everything was going smoothly for Dan and Olivia until they decided to partake in an ill-advised night of passion with Vanessa. Soon, the trio realized that things were getting way too complicated, and subsequently, Olivia broke up with Dan, leaving him free to confront his true feelings for Vanessa.

Serena and Gabriel’s relationship was filled with drama from the beginning. Their whirlwind romance really kicked off with a tipsy impromptu wedding ceremony in Spain and ended with financial theft. Still, somewhere along the way, the pair managed to develop genuine feelings for each other. Unfortunately, Gabriel’s girlfriend, Poppy, prevented them from pursuing anything more than just a fling. Although it was difficult for them to stop seeing each other, it was probably for the best, considering how Gabriel willingly lied to Serena throughout most of their relationship.

Rufus and Lily’s star crossed romance felt meant to be, but we can see why Lily chose to marry Bart despite her intense feelings for Rufus. Bart represented financial security for her children, and marrying him meant leaving Serena free to date Dan without complications. But love finds a way, and despite being married, Lily grows closer to Rufus to the point where she’s prepared to leave Bart. Of course, nothing ever goes according to plan on the Upper East Side.This love triangle reappeared so often throughout the series that it’s a miracle Lily eventually decided between them.

Here, we witnessed two Brooklynites battle it out for Nate’s attention. Things began escalating when Vanessa selfishly intercepted Nate’s love letter to Jenny to keep him for herself, but the real drama started once the Snowflake Ball rolled around. Jenny decides to seek revenge by making Vanessa a sheer dress to humiliate her in front of everyone at the dance. Despite her scheming, Jenny ends up with the short end of the stick when Nate chooses Vanessa over her. This complicated situation brought out the competitive side in both Jenny and Vanessa, and things got pretty ugly - all this for a guy.

In this romantic entanglement, Blair found herself between the clean-cut Nate Archibald, and the erratic but ever-charismatic Chuck Bass. Blair and Chuck first hook-up during season one, while Blair was broken up with Nate. But of course, seeing Chuck and Blair together causes Nate to re-think their relationship, and he comes scrambling back to Blair. Blair seemed to have genuine feelings for both but, especially in the second season, it seemed as though Chuck and Nate were vying for Blair’s affection more so that they could one-up each other and assert their dominance.

Sometimes, we can’t help but go back to what we know best. After ending her tumultuous affair with Tripp, Serena and Nate finally become an item again but their relationship is anything but smooth sailing. Serena’s difficult family life and search for her biological father complicates things as she turns to Dan for comfort rather than confiding in Nate. Of course, Dan and Serena can never stay “just friends” for very long and eventually, they share a kiss. This love triangle is proof that Dan and Serena can’t be kept apart - even when they’re in relationships with other people.

Louis and Blair’s relationship felt like something out of a fairy tale. The pair met in Paris and experienced a whirlwind romance, culminating in Louis revealing his royal lineage and proposing to Blair. Everything seemed perfect until Chuck came along. This complicated relationship perfectly represented the tension between Blair’s two greatest desires. On the one hand, she always sought the picture-perfect preppy Upper East Side life, and Louis was her golden ticket to privilege, prestige, and even a royal title. On the other hand, Chuck represented the full extent of her complicated personality and revealed to Blair that true love is more important than fitting into high society.

This is the love triangle that started them all. Spanning numerous years, the relationship between Serena, Nate, and Blair was essentially the main source of drama and tension in season one and resurfaced multiple times throughout the series. The origins of this love-triangle are basically a part of “Gossip Girl” lore. We all know the story of how Nate cheated on Blair by hooking up with Serena after a wedding, and how this event prompted Serena to leave New York for a while. For a long time, Nate remained a sore spot between the girls, but at the end of the day, the Serena, Nate, Blair relationship proved just how strong Serena and Blair’s friendship really was.