1. Hilary Duff, Lindsay Lohan, Aaron Carter
The early 2000s teen drama centered on Hilary and her then-boyfriend, Aaron. They started dating when she turned 13, and after a two-year relationship, he suddenly started seeing Lindsay out of the blue, telling CNBC in 2005: "I was dating [Hilary] for like a year and a half, and then I got a little bored, so I went and started getting to know Lindsay."
Hil and Aaron reunited a few months later, but he cheated on her again. Hilary and Lindsay hated each other for years, feuding back and forth until 2007 when the two publicly declared a truce. The teen love triangle was complicated, and the details are still scant, but from what I can tell, emotions were running high and Aaron was a complete jerk.
2. Miley Cyrus, Selena Gomez, Nick Jonas
Ah, our teenage years! They were marked by a heated debate: did we want Nick to stay with Miley or Selena? Who was the best fit? There were many awkward moments in this love triangle. For those of you who don't know, Miley and Nick dated when they were young between 2006 and 2007 (and even has an episode in Miles to Go, aka Miley's memoir).
He allegedly broke up with her and started dating Gomez. Miley was jilted and wrote the iconic song "7 Things" about her ex. She even sang the hit when Gomez was in the audience at the Teen Choice Awards in 2008. It was a back-and-forth, with Miley poking fun at Selena on her YouTube channel. Miley and Nick later collaborated on the 2009 hit "Before the Storm," and were rumored to get back together. Stars nowadays chalk it up to childhood drama, but we swear it was one hell of a ruckus back then.
3. Kourtney Kardashian, Scott Disick, and Sofia Richie
Kourtney and Scott were together on and off for years. They have several children together. We've seen his ups and downs on KUWTK, and then around 2015, it came to a head, and Scott was with a much younger Sofia. His father, you know, Lionel Richie, disapproved of it. Kendall commented on shady things in an Instagram post.
They were together for almost three years, and Sofia was even on the show at one point. Kourt and Scott were raising their children, but it was just awkward. Eventually, Scott and Sofia broke up, and as we all know, Kourt is head over heels in love with Travis Barker these days. Sofia is even happily engaged! Although the love triangle was a bit complicated, with much history to unravel, now everyone seems to have settled down.
4. Olivia Wilde, Jason Sudeikis, and Harry Styles
Olivia and Jason were engaged and had two children, it seemed like they were a solid couple. Suddenly, they parted ways. Then we saw the director walk out with Styles at a wedding holding hands like it was nothing serious, and maybe she wasn't and enough time had passed. .... But how did we come to this? Their debut as a couple was months ago, but things are still a bit tense today. Jason recently handed Olivia some documents at her CinemaCon premiere for Don't Worry Darling. (Which, in case you didn't know, Harry stars opposite Florence Pugh) Where is this drama headed?
5. Olivia Rodrigo, Joshua Bassett, Sabrina Carpenter
It seems the internet blew up when Olivia dropped "Drivers License," and people quickly linked it to her High School Musical: The Musical: The Series co-star. As the lyrics said, she was mourning a breakup. Things got very intense when detectives found out Bassett was now with Sabrina, and as the lyrics on Rodrigo's debut album Sour reveal on the track "Traitor," he didn't technically cheat on her, but he's still a traitor. People started to hate Sabrina, and the internet was abuzz with rumors about Olivia and Joshua breaking up. What was the timeline? He cheated on her and left her for Sabrina? How can you know the true answer?
