30 Celebrities Who Have Dated The Same Person

Ashton Kutcher and Demi Moore quickly made headlines when they started dating despite their 15-year age gap. They tied the knot in 2005 but split in 2011.

Two years after the No Strings Attached star finalized his divorce from Moore, he wed Mila Kunis in a private ceremony at The Secret Garden at Parrish Ranch in Oak Glen, Calif.

One of Hollywood's most high-profile love triangles, Brad Pitt found himself torn between Jennifer Aniston and Angelina Jolie.

The actor was married to the F.R.I.E.N.D.S. actress when he started working on Mr. and Mrs. Smith with Jolie. His onscreen romance with the Maleficent star soon bloomed off-screen, leading him to leave his wife of five years.

Cameron Diaz added Justin Timberlake and Jared Leto to her long list of well-known boyfriends. The now-married actress dated the former *NSYNC member for four years, while she also had a romance with the Suicide Squad star and reportedly got engaged at one point.

Giuliana Rancic made headlines after releasing a memoir that revealed that Jerry O'Connell cheated on her with the Spice Girls member Geri Halliwell.

He responded to the claims while appearing on Watch What Happens Live!, saying that his ex is a very nice girl.

"I don't want to say anything negative," he said. She's a very nice girl. We had a very fun time. It was decades ago. I don't believe cell phones were used then. It was like horse and buggy… It was a while ago."

The same cheating allegations emerged after his split from the musician, though Halliwell dismissed the claims.

John Mayer became the subject of Taylor Swift's songs when they broke up after dating between 2009 and 2010 when she was 19 and he was 32. The Lover singer notably wrote the tracks Dear John, The Story of Us, Ours, Superman, Foolish One and Would've, Could've, Should've.

Meanwhile, he also dated Katy Perry from 2012 to 2015, years before she got engaged with Orlando Bloom in 2019.

Justin Bieber had on-again, off-again relationships with both Selena Gomez and Hailey Bieber, but he married the model in the end.

Justin and Selena dated from 2010 to 2018. In one of their breakups, the Ghost singer sparked dating rumors with the supermodel after sharing a photo taken during their tropical vacation.

A source revealed to Entertainment Tonight that Justin started dating Hailey again after his split from the Lose You To Love Me singer. Only a few weeks later, TMZ confirmed the now-husband-and-wife's engagement.

Justin and Hailey officially tied the knot on September 30, 2019, following initial marriage rumors.

Before Kelly Preston died on July 12, 2020, she shared a romance with several actors, including George Clooney and .

She and Clooney dated for over a year, from 1987 to 1989, but they eventually married other people. Meanwhile, the late actress ended things with Sheen after a shooting incident happened.

"I was downstairs early in the morning making coffee and I thought she was still asleep upstairs," the actor told his My Violent Torpedo of Truth tour audience. "And I heard a f------ gunshot go off. I thought, 'She did it, she finally f------ did it. She killed herself and they're going to f------ blame me.'"

Both relationships Kim Kardashian had with Ray J and Kanye West did not happen to last.

She infamously had an alleged sex tape with Ray J long before she met West. Meanwhile, she shouldered another problem after marrying the Jesus Is King rapper because of his problematic behavior.

Matthew McConaughey dealt with different romance rumors before finding his great love.

He met Janet Jackson in February 2002, and an Entertainment Tonight report said they hit it off after the event and had a date.

"He is a great guy and such a sweetheart. It was just for a minute, that's why I am so hesitant to mention it," Jackson told Upscale Magazine.

Meanwhile, the actor dated his A Time to Kill costar Sandra Bullock for two years after meeting on the set in 1996.

Former heavyweight world champion Mike Tyson grew close to Naomi Campbell for a long time, it resulted in romance rumors. His close confidant, Rory Holloway, revealed in his book Taming The Beast- The Untold Story of Mike Tyson that they met at a party. After they fling, they never took their relationship to the next level.

He previously dated Robin Givens and married her in September 1988 after a year of dating. Their marriage only lasted for months as they divorced on Valentine's Day in 1989.

Before A$AP Rocky, Rihanna dated several men, including Drake and Chris Brown.

Her romance with the LAUGH NOW CRY LATER rapper went through ups and downs and lasted only until 2016. Meanwhile, her relationship with the Freaky Friday hitmaker became a hot topic as Brown assaulted the mom-of-two several times throughout their two-year relationship.

Bullock added Ryan Gosling to the list of men she dated, and he also had a romance with Rachel McAdams.

The La La Land actor and Bullock split in 2003 after two years of relationship. He also sparked a connection with his The Notebook costar from 2005 until they parted ways in 2007.

Scott Disick and Kourtney Kardashian through a mutual friend in 2006, and their relationship progressed as they welcomed their three kids: Mason, Penelope and Reign. They never got married, and the Poosh founder eventually tied the knot with Travis Barker.

Their breakup led Disick to date young models, including Sofia Richie, with whom he had a decade-long on-again, off-again relationship.

Clooney and Talia Balsam tied the knot in Las Vegas in 1989 but divorced in 1992. The actor told Vanity Fair in 1996 that he "married the one girl" he "truly loved and had loved for years."

Balsam soon moved on with John Slattery and married in 1998.

Tom Cruise is having some sort of impossible mission as he continues his search for true love. He had failed relationships with Katie Holmes and Cher, and he has tried moving on with other women but has not found the right one yet.