When obscenely wealthy kids are left unsupervised to mingle within themselves and other extremely powerful people, it leads to love triangles and scandals, especially on Gossip Girl. Without the romantic drama, the show would cease to exist - the notorious blogger fed off of rumors, whispers, and tittle-tattle to survive.
Some entanglements were innocent and heart wrenching for at least one of the three people involved, but some GG affairs were quite shocking and wicked even by the show's standards. While some love triangles were among the gang and their inner circle, they also played with royalty more than once, as well as actors and socialites for some truly controversial stories.
10 Dan, Serena & Nate
Lonely Boy and Serena could hardly stay away from each other, even when Serena was dating Nate. After her affair with Tripp left her in hospital, Nate rode in like a knight in shining armor and put Serena back together again in some of the most romantic scenes on Gossip Girl.
However, Serena leaned on Dan for support when she was looking for her father, and it was natural that something sparked between the former lovers when she did. This triangle was heartbreaking for Nate, because he was continuously made to feel like his love was inadequate. But this wasn't really controversial.
9 Chuck, Blair & Dan
Chuck and Blair's love story was one that never really faded - it always reared its head when Blair would date someone new. After her disastrous wedding to Prince Louis, Dan gave her the safety and support that she needed, which culminated in a sweet relationship between them.
While unusual, this love triangle managed to raise a few eyebrows because of Dan and Blair being the primary couple, and her soulmate on Gossip Girl was on the sidelines. It was just strange to see Blair siding with anybody else over Chuck in this imbroglio.
8 Vanessa, Nate & Jenny
Both the Brooklyn girls on Gossip Girl had a crush on Golden Boy Nate, and they went to great lengths to fight over him. Nate and Jenny had a few brief moments of affection before Dan told Nate to leave his house because of Jenny's age, and then they never heard from each other again.
But Nate did attempt to reach out to Jenny through a letter which was intercepted by Vanessa and destroyed. There was plenty of drama in this triangle, and the open catfight over a boy became the talk of the town. In fact, Jenny found out and humiliated Vanessa at a school dance by giving her a see-through dress to wear as a fake sign of truce.
7 Chuck, Blair & Nate
A triangle that kept shifting, the tussle for Blair between Nate and Chuck got very sticky, very quickly. Initially, both the Upper East Side boys had left Blair alone because Nate couldn't handle the aura of infidelity, and Chuck was being sexist about her sex life, but the tides turned very soon.
All in all, the fight between two best friends over Blair was pretty newsworthy in their circles. Both the men were in a clash of egos, and they even got into a fistfight in front of St. Jude's some time earlier over Blair. With the two most eligible bachelors fighting over the Queen B of Manhattan, things got heated very quickly.
6 Serena, Nate & Blair
The entanglement that started it all, this one was hugely unfair on Blair but set her on the path to meeting other suitors, like Chuck. Blair and Nate had been together since they were kids, and would have continued into adulthood had the fateful rendezvous between Serena and Nate not happened.
This was a spicy one since Blair never found out (only a couple years later), and Serena skipped town out of embarrassment without even letting her best friend know. Blair felt betrayed by both her closest confidantes and the big treachery was gossiped about in their school - and even outside it.
5 Serena, Gabriel & Poppy
Serena knew how to have tabloid-worthy romances, and this liaison between her and Gabriel and Poppy was pretty contentious. A triangle that ended with the It Girl going to jail and a criminal going unpunished - things couldn't get more problematic. Serena had decided to flee to Spain with her socialite friend Poppy and her boyfriend Gabriel, but the trip ended with Poppy leaving and Gabriel and Serena having a whirlwind intoxicated wedding.
When Gabriel returned, he struck an affair with Serena, but drained her near and dear ones of money, with Poppy as the mastermind of the plan. The whole saga ended with the return of catty Georgina on the Upper East Side.
4 Rufus, Lily & Bart
Despite their children being in the spotlight for a majority of Gossip Girl, the parents sometimes stole the show too. Rufus and Lily's romantic saga was one for the books - they had road trips, music tours, and unforgettable nights which time could not diminish the glory of.
Lily wanted safety and wealth, so she chose to marry Bart despite Rufus being her true love. This love triangle between a billionaire entrepreneur, a famous socialite, and a former rock band member was something worth writing about, especially because it meant that the elite Bart Bass was being cheated on emotionally, before, during, and after his marriage.
3 Vanessa, Dan & Olivia
His entry into NYU brought several ladies buzzing towards Dan, including extremely famous actress Olivia. Olivia by herself was a star with controversies that followed her, but her relationship with Dan was embarrassingly publicized on the Jimmy Fallon show too.
To top it all off, Dan, Olivia, and Vanessa decided to have a threesome before Olivia left NYU. Funnily enough, this led to extreme conflict between both the women as they vied for Dan's attention. For a young star at the peak of her career to be fighting for a college boy earned some choice reactions from people, and also created buzz which wasn't necessarily the good type.
2 Chuck, Blair & Louis
Another Chair vs. the world triangle, but the enemy of their love this time was the prince of Monaco. Blair was getting everything that she had ever dreamed of - a loving prince, a royal title, even more privileges - and she chose that over the passion that she shared with Chuck, despite Chuck beseeching her not to marry Louis till the last moment.
For a business scion and real life royalty to be fighting over Blair Waldorf was pretty controversial, especially with Blair's pregnancy and the bomb that Louis dropped on her after the wedding - she had a farcical marriage to him and a hefty dowry to pay if she wanted to escape. The world loves watching monarchs squirm, and this juicy triangle provided enough fodder.
1 Blair, Marcus & Catherine
What started off as a fairly boring romance turned into an explosive love triangle between Blair, Lord Marcus, and his stepmother Catherine. The Queen B went to all lengths to please Marcus and his tough stepmother in season 2, but none of it could culminate into anything because Marcus was hooking up with his father's wife secretly.
This was easily one of the most questionable and illicit affairs between three people on the show, since it involved incest, blackmail, infidelity, and dirty monetary transactions, mostly on Catherine's part. If this were to happen in the age of social media, it would have exploded at a bugger magnitude than it did on Gossip Girl.
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July 22, 2021 at 12:00AM
