Celebrities Whove Dated Their Exes Best Friends

As awkward as it may sound, these stars find new love not too far from their exes’ inner circle that in some cases ruin the friendships between two best friends.

AceShowbiz – When someone is dating a boy or a girl they love, they’re not only getting to know their boyfriend/girlfriend, but also their boyfriend/girlfriend’s family and friends. Most of the time, after hanging out together several times, they also get close to the family members and pals.

For some reasons that not everybody has got to experience, some celebrities have kept in touch with their exes’ best friends even after they’ve broken up. Some others may accidentally bump into their exes’ best friends through their mutual connections and new love develops among them.

As awkward as it may sound, here are some celebrities who have dated their exes’ best friends.

1. The Weeknd

The Weeknd seemingly couldn’t completely cut ties with his ex Bella Hadid. Having dated the model on-and-off from 2015 until they split for good in 2019, the “Starboy” crooner has been rumored to be linked to Simi Khadra from the twin duo Simi Haze, who was once close to his former girlfriend.

When the dating rumors started circulating in April 2021, Bella immediately hit the unfollow button on both The Weeknd and Simi’s social media accounts. The pair’s romance has never been confirmed, but recently they were caught kissing during the Canadian star’s birthday bash in Las Vegas, which said everything about their relationship status.

2. Michael Sheen

Michael Sheen has been known as that lucky guy who has been with pretty girls, including Kate Beckinsale and Sarah Silverman. The “Masters of Sex” alum was married to the “Underworld” star from 1995 until 2003, during which they welcomed a daughter named Lily.

After several other failed relationships, the Welsh actor fell in love with Sarah in 2014. Despite their apparent chemistry in “Doug Loves Movies“, they called it quits in 2018 and the stand-up comedian interestingly found a confidant in Kate. They even joked on Instagram about their shared comfort food, M&M’s.

3. Luke Wilson

Luke Wilson‘s long list of celebrity exes include Drew Barrymore and Gwyneth Paltrow, who have been friends for pretty much all of their lives. They share a godfather in Steven Spielberg and apparently had a similar taste in men.

Drew dated Luke first for two years from 1997 to 1999. Their breakup was amicable as evidenced by the “50 First Dates” star casting the “Legally Blonde” actor in her movie “Charlie’s Angels” (2000), which she starred in and produced. Luke later dated Gwyneth, his co-star in “The Royal Tenenbaums” (2001). While his romance with Gwyneth was a brief one, her friendship with Drew has remained strong.

4. Julia Roberts

Back in her heyday, Julia Roberts was one of the “it girls” that everyone was dying to date. So strong her charm was that Jason Patric was willing to sacrifice his friendship with Kiefer Sutherland to be with her. After calling off her engagement to the Jack Bauer of “24” in 1991, just three days before their scheduled wedding, she ran off with Kiefer’s best friend, Jason, and flew to Ireland. Julia’s relationship with Jason didn’t last long either as she quickly married country singer Lyly Lovett in 1993 after their split.

Years later, Kiefer and Jason managed to patch things up around 2009 and even talked about their reunion in a 2021 podcast. “When I saw him again, it was more of a laugh and a toast,” Patric shared, “They both [Kiefer and Julia] have been subsequently married since, a couple times … and what lasted after all that is me and Kiefer, 35-year buddies.”

5. Ian Somerhalder

Talking about sharing a common boyfriend, one may want to learn from Nina Dobrev and Nikki Reed. The two actresses remain best friends even after the “Twilight Saga” star married “The Vampire Diaries” alum’s ex-boyfriend, Ian Somerhalder.

Sparks flew between Nina and Ian when they were starring on the CW supernatural drama series. They dated for four years until 2013. In mid-2014, he began dating Nikki and they tied the knot in 2017. While some might have expected tension between the two ladies, they’re still friends to this day, with Nina sometimes hanging out with the couple even after they’re married.

6. Apryl Jones

It’s a completely different case for Apryl Jones, Omarion and Lil’ Fizz. Things got weird and tense between them after the female singer/songwriter was romantically involved with Lil’ Fizz, who is the groupmate of her ex and baby daddy Omarion.

Omarion’s strong reaction to Apryl and Lil’ Fizz’s relationship was well-documented on social media and “Love & Hip Hop: Hollywood“, but eventually friendship prevailed over love. After he called it quits with Apryl in 2020, Lil’ Fizz publicly apologized to his fellow B2K member onstage during the “The Millenium Tour 2021”.

7. Richie Sambora

Things were also pretty messy between Heather Locklear and Denise Richards as they were both romantically involved with Richie Sambora, albeit not at the same time. Following the end of her marriage to the guitarist, the “Melrose Place” alum was reportedly so heartbroken.

But instead of consoling Heather, who was her close friend, Denise came to help Richie get through the split by being his new leading lady. In her defense, the “Starship Troopers” star claimed that her friendship with Heather was fractured way before she became involved with Richie. Their romance was short-lived, but the two actresses never repaired their friendship.

8. Adam Duritz

If one didn’t follow Jennifer Aniston and Courteney Cox‘s love relationships in the past, they might be shocked to learn that they share an ex-boyfriend. Both of them once dated Counting Crows frontman Adam Duritz. The singer met Jennifer first and had a brief romance in 1995, during the early days of her popular sitcom “Friends”, through which she struck a friendship with Courteney.

Several years later, Adam was linked to Courteney, Jen’s best friend on- and off-screen, after she starred in his band’s 1997 music video for “A Long December”. Jennifer apparently never took issue with it as she and Courteney are still close friends to this day relatively without any drama.

9. Katie Holmes

No one would’ve guessed that Katie Holmes would move on from her dramatic split from Tom Cruise with his close friend Jamie Foxx. The two actors bonded after they starred together in 2004’s “Collateral“, before Tom began dating Katie.

After Tom and Katie’s marriage legally ended in 2012, she was rumored to be romantically involved with Jamie in 2013. They never confirmed it and kept their relationship under the radar for years, until they finally went public in 2019. Unfortunately, they split shortly afterwards.

10. Taylor Lautner

Taylor Lautner‘s fling with Taylor Swift may be widely known because of her song “Back to December”, but he also dated her BFF Selena Gomez. In fact, the Jacob Black of the “Twilight Saga” movie series showed his interest in the “Wolves” singer first in 2009, after they met in Vancouver while filming separate movies there.

The 30-year-old never pursued things further with Selena, reportedly ghosting her after several dates. A few months later, sparks flew between him and the “Love Story” hitmaker on the set of “Valentine’s Day“, but it didn’t last long either. While Selena could’ve been easily angry at the Grammy Award-winning artist, their friendship is as strong as ever today.

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