The Best Love Triangles of All Time, Ranked

1. Art, Tashi, & Patrick — Challengers

Art, Tashi, and Patrick really upped the ante for every love triangle ever. Not only did I actively want Tashi to pick Art and actively want her to pick Patrick...I also wanted them to all three be together? I mean, have you ever rooted for three people to kiss so much? (Don't answer that question — that can be your little secret.)

Seriously though, Challengers served up a love triangle that really makes you ask what makes the right relationship, if that changes over time, and how much any relationship can handle if you don't love yourself...and if a sport can ultimately be your third. ;)

2. Harry, Lucy, & John — Materialists

"Broke man propaganda" this and "broke man propaganda" that — Materialists is one of my favorite modern love triangles. So while the haters debate whether or not Lucy should have picked one suitor over the other, I can't help but relish in how torn I was for her. Does she pick someone she has such a storied past with? Does she pick someone who can give her everything she ever wanted? Are those two things mutually exclusive? Ugh, BRB while I go watch this again.

3. Conrad, Belly, & Jeremiah — The Summer I Turned Pretty

Season 1 of The Summer I Turned Pretty premiered in June 2022, and the show has kept viewers in a chokehold ever since. It centers on Isabel "Belly" Conklin, who summers at her mother's best friend Susannah's beach house and finds herself torn between Susannah's two sons: Conrad and Jeremiah.

Fans get to follow themes of first love and heartbreak, all against the backdrop of a magical teen summer. What more could we ask for? The only question that remains is who you're rooting for in Belly's love life: complex Conrad or the more easygoing Jeremiah.

4. Mr. Big, Carrie, & Aidan — Sex and the City

No matter how much you love Carrie, there's no denying that she's made us want to bang our head against a wall on more than one occasion. And most of those instances are linked to her love triangle with Mr. Big and Aidan Shaw.

As she navigates love in Manhattan, she finds herself pining after Mr. Big, no matter how many times he lets her down and breaks her heart. So, when Aidan Shaw enters the picture and shows he could provide a much different relationship experience, Carrie gets caught in a conundrum: she has to choose whether to chase passion or stability. Spoiler alert: the latter loses.

5. Meredith, Derek, and Addison — Grey's Anatomy

Meredith Grey caught a rough break at the start of Grey's Anatomy. First, she unknowingly sleeps with one of her brand-new bosses the very night before she starts her intern year. Then, as she begins to let her guard down and consider a potential romance with Dr. Derek Shepherd (AKA "McDreamy"), she comes face-to-face with his wife, Addison Montgomery.

Things seemed dicey at the end of Season 1, after Addison showed up in Seattle and Meredith thought Derek was just a cheater. But thankfully, the details of his separation from his wife were soon revealed, and Meredith's legendary push-and-pull love story with Derek was put back on track for a while.

6. Joey, Dawson, & Pacey — Dawson's Creek

Few teen dramas defined the late '90s like Dawson's Creek. The series chronicled the life of Dawson Leery, an aspiring filmmaker, and his relationships with his female bestie, Joey, his friend Pacey, and a new girl in the neighborhood, Jen.

Viewers fell in love with Joey, who'd had a crush on Dawson ever since they were kids. However, they also saw potential sparks with Pacey, which led to the creation of an iconic TV love triangle. And unlike in Gilmore Girls, at least fans got to find out who Joey finally wound up with in the end.

7. Chuck, Blair, & Nate — Gossip Girl

8. Peyton, Lucas, and Brooke — One Tree Hill

Another classic Y2K drama was One Tree Hill. The show, set in Tree Hill, North Carolina, follows the lives of high school half-brothers Lucas and Nathan Scott. And, obviously, it wouldn't be a true high school show without some romantic intrigue.

So, a central plot of the first few seasons concerns Lucas' love triangle with his best friends, Brooke Davis and Peyton Sawyer. Prepare for spoilers: it's not until Season 4 that Brooke ultimately breaks up with Lucas, and he finally realizes that Peyton is the girl he should be with. Queue the Lucas-Peyton kiss that sent so many fans' hearts soaring.

9. Dean, Rory, & Jess — Gilmore Girls

Searching for small-town vibes with a slice of fall comfort pie? Gilmore Girls is your answer. But while this feel-good show is quite tender and innocent in the beginning, centering on the smart yet socially awkward Rory Gilmore, she evolves into a pretty controversial character.

Why? Well, her multiple love triangles, of course! The show premiered in 2000, and more than two and a half decades later, diehard fans are still arguing over who Rory should've ended up with. There was the boy next door, Dean, the brooding and emotionally avoidant Jess, or the charming and privileged Logan. Since Rory had so many tropes right at her fingertips, though, I guess it's understandable why she flip-flopped from time to time.

10. Stefan, Elena, & Damon — The Vampire Diaries

After The Vampire Diaries debuted in 2009, Nina Dobrev took on the role of main character Elena Gilbert for six whole seasons. Similar to The Summer I Turned Pretty, she also got caught in a famous love triangle with two brothers (but with a more supernatural twist).

Elena first befriended the sweetheart Stefan Salvatore, but eventually, his black-cat energy brother, Damon, started to steal her attention. Such a setup created the iconic love triangle that so many teen girls continue to debate over to this day.

11. Edward, Bella, and Jacob — Twilight

Last but certainly not least is Twilight, a quintessential saga that's practically synonymous with the term "love triangle." Once Bella moves to Forks, Washington, in the very first film, the seeds are quickly planted: Edward or Jacob?

I remember going to the midnight premiere of New Moon in 2009, sporting a "Team Edward" t-shirt that makes me cringe internally now. But no matter how embarrassing that may seem, it epitomizes the central Twilight debate over who Bella should be with: the cold, handsome, and mysterious vampire, or the warm, golden-retriever-like werewolf? Let's be real: we all chose a team, and despite my happiness with Bella's final choice, plenty of fans were still disappointed.