12 Stars Who Didn’t Find It Awkward to Date Their Friend’s Ex

Love triangles are often the stuff of romance movies and dramas, and are mostly inspired by real-life experiences. Statistics suggest that adults are inevitably involved in these situations. A study even revealed that one-third of adults in the US have been in intertwined relationships, and maybe that number includes our beloved Hollywood stars.

1. Selena Gomez and Taylor Swift

Selena is one of Taylor Swift’s closest friends, and she’s even a member of Taylor’s star-studded “squad.” However, their longstanding friendship isn’t the only thing they have in common. They also happened to date Twilight actor Taylor Lautner. Both pop stars were romantically linked to the actor in 2009.

2. Cameron Diaz and Kate Hudson

Both blonde beauties didn’t just share one former lover — they also dated each other’s exes. When Cameron ended her 4-year relationship with singer Justin Timberlake, Justin and Kate began dating not long after. And afterward, Cameron dated Kate’s ex-boyfriend, football player Alex Diaz.

However, the past became past when the 2 appeared together at an Oscars party all cozied up. Both are again gal pals together with the rest of the Hollywood A-listers.

3. Nikki Reed and Ashley Greene

Nikki and Ashley’s sisterhood in Twilight spanned beyond the screen. The duo still hangs out, and Nikki even co-hosts Ashley’s podcast. Their love for each other has sustained despite the fact that both of them dated actor Ryan Phillippe. Nikki dated Ryan in 2007, and Ashley was romantically linked to him 6 years later.

4. Kiefer Sutherland and Jason Patric

Julia Robert’s chick flick The Runaway Bride may be based on happenings from her real-life love entanglement with best friends Kiefer and Jason. Julia was set to marry Kiefer in a lavish wedding in 1991. However, the marriage didn’t push through as Julia reportedly ran away with Jason on the day they were supposed to exchange "I Do"s. Julia and Jason broke up a year later.

The 2 put their drama to rest more than 2 decades later, addressing their tiff over Julia together in a podcast.

5. Jennifer Aniston and Courteney Cox

The decades-long friendship between Jen and Courteney has seen its ups and downs. After sharing the screen in the fan-favorite Friends, the pair became inseparable, even now. Their brief entanglements with Counting Crows’ Adam Duritz had no effect on their bond.

6. Drew Barrymore and Kristen Wiig

The comediennes not only have a way of making us laugh, but they also share a romantic history with The Strokes drummer Fabrizio Moretti. After Drew ended her 5-year relationship with him, her pal Kristen gave theirs a go. However, Drew was very cool when she learned about their budding romance. “It all seems so wacky... but that’s kind of how life works,” she shared.

7. Kendall Jenner and Hailey Bieber

Before becoming Mrs. Bieber, Hailey Baldwin was just a fan and a good friend of Justin’s, and her supermodel BFF Kendall initially had a short fling with Justin, which started in 2015. However, Kendall was supportive when it came to Hailey’s true love. She even attended their wedding and threw Hailey’s bachelorette party.

8. Justin Bieber and Shawn Mendes

The Canadian pop stars have shown their great bond over the years, and their seemingly “bromantic” exchanges are undeniably adorable. But before Justin tied the knot with model Hailey Baldwin, Shawn and Hailey used to date.

However, professionalism and friendship always got things going between the 2, and all has returned to normal. They even collaborated on a song in 2020.

9. Owen Wilson and Lance Armstrong

Yet another love triangle between 2 pals ensued when Lance Armstrong pursued actress Kate Hudson while Kate had a falling out with one of Lance’s good friends, Owen, whom she dated on and off. However, all are now happy with their partners.

10. Tom Cruise and Jamie Foxx

When the movie Collateral was filmed, Tom and Jamie struck up a friendship on set. This happened when Tom was still married to actress Katie Holmes, with whom he had one daughter. However, when Katie stopped being Mrs. Cruise after 6 years of marriage, Jamie decided to give it a try with her. Their romance lasted for 6 years too.

11. Katy Perry and Taylor Swift

The hitmakers both experienced whirlwind romances with fellow artist John Mayer. Taylor first dated John in 2009, and 4 years later, after things ended between them, Katy and John were seen together for a year. They even performed a song together.

But their friendship has remained strong, and they recently affirmed it with a collaboration on Taylor’s song “You Need to Calm Down.” Katy showed up in the music video.

12. Elizabeth Taylor and Debbie Reynolds

One of the biggest shocks in 1950s Hollywood was the divorce of actors Debbie Reynolds and Eddie Fisher and Eddie’s eventual relationship with one of Debbie’s best friends, Elizabeth Taylor. Their friendship goes back to even before Debbie was her matron of honor at her wedding with Mike Todd. But when Mike suddenly passed away, Elizabeth found comfort in the recently divorced Eddie.

Years later, they eventually got past it and treated the love triangle as a hiccup in their friendship. According to Debbie, their friendship was worth more than that. The 2 remained friends and even starred in a movie together.

How would you feel if you were in a love triangle? Have you had a similar experience as these celebrities?