From Taylor Swift and Katy Perry to Ray J and Kanye West: 10 Celebs Who Dated the Same Person
Here Are 10 A-Listers Who Have Had a Relationship With Same People
Hollywood is full of drama, and celebrity relationships are often at the center of it. Many stars have a string of high-profile romances, with their dating histories reading like a who's who of the industry. From teen idols to Oscar winners, A-listers typically tend to stick to their own, forming the ultimate celebrity power couples, even if they date for a shorter duration. Whether it's an on-set romance turned off-screen love, a whirlwind celebrity fling, or a relationship the tabloids just won't let go of, there's always fascination around who's dating who in Hollywood. So, here are a few celebrities who have dated the same famous person.
1. Demi Moore and Mila Kunis: Ashton Kutcher
Even though Ashton Kutcher and Demi Moore were 15 years apart in age, they made news as soon as they started dating. The No Strings Attached star married Mila Kunis in a secret wedding at the Secret Garden two years after he and Moore finalized their divorce. Now, Kutcher seems happy with his marriage to Kunis and their two kids. But things weren't always that perfect in his personal life at one point. Moore and Kutcher were wed from 2005 till 2013; however, the couple's marriage abruptly ended, and even years after their widely reported divorce, several accusations continued to be made, as per The Things.
2. Jennifer Aniston and Angelina Jolie: Brad Pitt
When he began filming Mr. and Mrs. Smith with Angelina Jolie, Brad Pitt was wed to Jennifer Aniston, the F.R.I.E.N.D.S. actress; as such, their five-year marriage ended when Pitt and Jolie's on-screen affair blossomed off-screen. Two months after announcing their separation, the Break-Up actress filed for divorce on the grounds of irreconcilable differences. She also went on to change her last name back to Aniston (from Pitt). Over the next few years, Pitt and Jolie captivated the world with their relationship. They became engaged in 2012, and Pitt and Jolie got married in France in 2014 before splitting up two years later. As it turns out, Aniston and Pitt are still 'buddies' more than 15 years after going through one of the most extensively covered breakups in Hollywood, as per People.
3. Justin Timberlake and Jared Leto: Cameron Diaz
Cameron Diaz expanded her list of famous boyfriends to include Justin Timberlake and Jared Leto. When they first met (allegedly at the 2003 Kids Choice Awards), Timberlake was 25, and she was 34. They dated for four years before splitting up, but the reason behind their breakup has never really been made public, even if various theories have been making the rounds on the internet. People also speculated in 2003 that Leto and Diaz were engaged when the actress was seen at the Golden Globes with a $15,000 ring on her finger. Leto and Diaz have never discussed their connection, yet there was some speculation that has never been verified that Leto penned the 30 Seconds to Mars song Attack with Diaz in mind, as per NickiSwift.
4. Taylor Swift and Katy Perry: John Mayer
Taylor Swift started writing songs about John Mayer when they split up in 2009 and 2010 when she was 19 and he was 32. The songs Dear John, The Story of Us, Ours, Superman, Foolish One, and Would've, Could've, Should've were written by the Lover vocalist, among others. Katy Perry also dated him from 2012 to 2015 before her 2019 engagement to Orlando Bloom. Additionally, when Swift released Bad Blood and the music video that goes with the track, it featured her squad of incredibly attractive and well-known friends. Many people interpret Swift's song lyrics to be her story of how her friendship with Perry didn't work out, as per Time.
5. Selena Gomez and Hailey Bieber: Justin Bieber
Justin Bieber's romantic journey involved a rollercoaster with Selena Gomez before finding lasting love with Hailey Bieber. Dating from 2010 to 2018, Justin and Gomez's on-again-off-again saga captured headlines. During one such split, Justin's vacation photo with Hailey sparked dating speculation. Following his permanent breakup with Gomez, Justin rekindled his romance with Hailey, leading to a speedy engagement that was confirmed by TMZ just weeks later. On September 30, 2019, Justin and Hailey officially became husband and wife, putting an end to swirling marriage rumors.
6. Ray J and Kanye West: Kim Kardashian
Kim Kardashian's relationships with Ray J and Kanye West were both extremely talked about and debated, even years after the breakups. Long before she even met West, The Kardashian star became infamous for a sex tape with Ray J, which many argue is what propelled her into becoming a media personality. After marrying the Jesus Is King rapper, she had to deal with another problem as a result of his behavior. Kardashian stated that West had met Ray J at an airport to get a computer and a hard drive that held 'all of the sex tape' and brought it to her during Season 1 of The Kardashians. There was 'nothing sexual' in the video, the beauty mogul reportedly said, as per Newsweek.
7. Janet Jackson and Sandra Bullock: Matthew McConaughey
Matthew McConaughey faced many romance rumors before finding true love. In February 2002, he crossed paths with Janet Jackson, sparking dating rumors. An Entertainment Tonight report claimed they connected at the Grammys and even went on a date. Jackson, acknowledging their brief encounter, praised McConaughey as a 'great guy' later on but remained guarded about why it didn't work out between them. But before that, McConaughey also had a two-year romance with Sandra Bullock, his A Time to Kill co-star, initiated on the set in 1996. Even though they went their separate ways, in an interview with Cosmopolitan, Bullock stated that they were great friends: "No matter where he is in his life or where I am in mine—he could be married—I know we would stay close."
8. Drake and Chris Brown: Rihanna
When Drake and Rihanna were persuaded to talk about their relationship, the phrase 'just friends' was frequently used. However, Rihanna made it very evident in a 2018 Vogue profile that after breaking up, they were no longer even friends. News initially broke out that Drake and Rihanna were reportedly sighted at Lucky Strike in New York City shortly after Rihanna's highly public breakup from Chris Brown in 2009 following Brown's infamous attack on the singer, according to Page Six. However, the Canadian rapper and Riri broke up due to scheduling conflicts and do not appear to be on the best of terms.
9. Sandra Bullock and Rachel McAdams: Ryan Gosling
Ryan Gosling has dated superstars Sandra Bullock and Rachel McAdams, both of whom he once referred to as 'the greatest girlfriends of all time.' After two years of dating Bullock in 2002, the actress and Gosling called it quits. Later, he sparked a relationship with his co-star from The Notebook from 2005 till their 2007 separation. Being the romantic he is, Gosling went on to say that his relationship with McAdams was nothing like what was shown in The Notebook! Furthermore, when discussing why he and Bullock ended their relationship, Gosling mentioned that there was a specific 'bad guy'—showbusiness—that came between them, as per Fandom Wire.
10. Katie Holmes and Cher: Tom Cruise
Tom Cruise, the star of Top Gun, has had three unsuccessful marriages and has been largely unlucky in love. The actor had a widely discussed and troubled relationship with Katie Holmes in addition to a 'hot and heavy' one with Cher. Yup! There may be many who didn't know Cruise and the legendary singer Cher first met in 1985, at the ages of 23 and 38, respectively, and had a brief affair. Cruise then started a highly publicized relationship with Holmes in April 2005. Before welcoming their daughter Suri into the world in April 2006, the couple made their first official appearance together in Rome. He tried moving on with other women after his unsuccessful relationships with Holmes and Cher, but he hasn't yet found the right one, although he is allegedly dating Russian socialite Elsina Khayrova.
