15 Messy Connections Between Celebs, Their Friends, And Their (Alleged) Exes

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15 Messy Connections Between Celebs, Their Friends, And Their (Alleged) Exes

Dating in Hollywood is kind of like dating in a really small high school where everyone you could date has already dated one of your friends. Basically, a lot of celeb couples already have a condensed version of a “six degrees of Kevin Bacon” connection before they start dating.

Here are 14 weird and unexpected connections between celeb couples and (alleged) exes:

1. Selena Gomez reportedly dated exes of both Hadid sisters.

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Selena is reportedly dating Zayn Malik, who was in an on-and-off relationship with Gigi Hadid from 2015-2021. For 10 months in 2017, Selena dated the Weeknd, who previously dated Gigi’s sister Bella from 2015-2016. He then got back together with Bella from 2018-2019.

2. Taylor Swift and Selena Gomez became friends when they were both dating Jonas Brothers. The following year, they both dated Taylor Lautner.

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In 2008, Selena briefly dated Nick Jonas, and Taylor briefly dated Joe Jonas. They became friends while going on double dates.

In early 2009, Selena dated Taylor Lautner while they were both filming in Vancouver. However, their relationship was short-lived, and in the fall, he dated Taylor Swift. They broke up in December.

3. Avril Lavigne is reportedly dating Tyga, who used to date Kylie Jenner. Avril used to date Kylie’s half-brother, Brody. One of Tyga’s other exes, Angela White (formerly known as Blac Chyna), used to date Kylie’s other half-brother, Rob Kardashian.

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Tyga dated Angela from 2011-2014. He then dated Kylie from late 2014 until 2017. Meanwhile, Angela was engaged to Rob, but they broke it off in 2017. 

Previously, Tyga was married to Jordan Craig for a month in 2010. Jordan is the mother of Tristan Thompson’s firstborn. Tristan was in an on-and-off relationship with Kylie’s half-sister, Khloé Kardashian, from 2016-2021.

Previously, Avril dated Brody from 2010-2012. She and Tyga were first spotted together in March 2023, two weeks after she called off her engagement with Mod Sun.

Avril is also signed to the record label owned by Travis Barker, the husband of Kylie’s other half-sister, Kourtney Kardashian Barker.

4. Counting Crows frontman Adam Duritz dated both Jennifer Aniston and Courteney Cox while they were filming Friends.

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After their mutual friends lied about them having crushes on each other, Adam and Jen met at The Viper Room and briefly dated in 1995.

Then, in 1996, Courteney appeared in Adam’s music video for “A Long December.” They then dated in 1997.

5. Sandra Bullock and Jennifer Aniston have a mutual ex-boyfriend — Tate Donovan. They actually became friends through him.

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Sandra and Tate dated from 1990-1995.

Then, he and Jennifer dated from 1995-1998, breaking up right before he played her love interest on Friends.

While interviewing Jen for Interview in 2020, Sandra said, “We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being. … We both partook of Tate…who was a very patient human being, given that he dated us both.”

6. Drew Barrymore and Gwyneth Paltrow, friends and fellow goddaughters of Steven Spielberg, both dated Luke Wilson.

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From 1996-1998, Drew and Luke were in an open relationship. 

In 2001, he entered a year-long relationship with his The Royal Tenenbaums costar Gwyneth Paltrow.

7. Cameron Diaz and Kate Hudson reportedly share two exes — Alex Rodriguez and Justin Timberlake.

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After Cameron presented Justin with the Kids Choice Award for Best Burp in 2003, they started dating and stayed together until 2007. He reportedly hooked up with Kate a few days later.

From 2010-2011, Cameron reportedly dated Alex, who previously dated Kate for a few months in 2009. 

8. Mark-Paul Gosselaar allegedly dated all three of his female costars on Saved by the Bell, Elizabeth Berkley, Lark Voorhies, and Tiffani Thiessen. Tiffani also reportedly dated Mario Lopez.

Paul Drinkwater / ©NBC / courtesy Everett Collection, Gary Null / ©NBC / courtesy Everett Collection

At some point during filming, he dated Elizabeth Berkley, which he confirmed in 2019.

He also reportedly dated Lark Voorhies for three years toward the end of the show’s run.

Series producer Peter Engel told ABC News that Tiffani dated Mark-Paul and Mario at different points during the show. 

He said, “Everybody dated everybody else except Screech.”

9. Stevie Nicks famously dated two of her Fleetwood Mac bandmates, Lindsey Buckingham and Mick Fleetwood.

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When they joined the band in 1975, Stevie and Lindsey were already in a long-term relationship, and they’d been friends since high school. However, they ended things before the 1977 release of Rumours. 

Mick remarried Jenny Boyd in 1977, but he also had a short affair with Stevie that year. He porced Jenny the following year.

Over the next few decades, Stevie and Linsdey were in and out of the band until 2018, when he was fired.

10. Yolanda Hadid was married to David Foster, who was previously married to Linda Thompson. Linda was previously married to Caitlyn Jenner. Yolanda’s son, Anwar, reportedly dated Caitlyn’s daughter, Kendall.

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Yolanda was married to Mohamed Hadid, the father of Anwar, Bella, and Gigi, from 1994-2000. Then, she was married to David from 2011-2017.

Previously, David was married to Linda Thompson from 1991-2005. However, before that relationship, she was married to Caitlyn Jenner from 1981-1986.

Caitlyn went on to be married to Kris Jenner from 1991-2015. Together, they had two daughters, Kendall and Kylie.

As teenagers, Kendall and Bella met online and became friends. After Bella, Kendall met Gigi, whom she also became friends with, and Anwar, whom she reportedly dated casually in 2018.

11. Joe Jonas dated both Taylor Swift and her close friend Gigi Hadid.

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Taylor and Joe dated for a few months in 2008 before he famously broke up with her in a 27-second phone call.

Seven years later, he briefly dated Gigi, and Taylor and her then-boyfriend Calvin Harris hung out with them.

12. Demi Lovato dated Joe Jonas and Trace Cyrus, whose siblings, Nick and Miley, also dated.

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As previously stated, Nick and Selena briefly dated in 2008. Previously, he dated Miley Cyrus from 2006-2007.

Joe dated Taylor while Nick was with Selena. Later, he briefly dated his Camp Rock costar Demi Lovato in 2010.

Demi dated Trace in 2009, then Joe in 2010.

Previously, Nick dated Miley in 2008.

13. Demi Lovato used to be close friends with Selena Gomez and the Jonas Brothers. During their Disney Channel days, Nick Jonas famously dated now-friends Selena and Miley Cyrus. His brother Joe dated Selena’s then-BFF, Demi, and her now-BFF, Taylor Swift.

Christopher Polk / Getty Images, Disney Channel / Via youtube.com

14. After Kaitlynn Carter separated from Brody Jenner, she briefly dated Miley Cyrus. Shortly after, Miley went on to date Cody Simpson, who used to date Brody’s half-sister, Kylie.

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In 2019, Kaitlynn and Brody announced their porce after a year of marriage (though they were never legally married). Right after, she went on vacation with Miley, and they had a short but dramatic relationship.

Shortly after, Miley began dating Cody, who previously dated Kylie in 2011.

Miley and Cody broke up 10 months later.

15. And finally, Justin Bieber reportedly dated both Kendall Jenner and her half-sister, Kourtney Kardashian Barker. He also dated Sofia Richie, who went on to date Scott Disick, Kourtney’s ex. Justin later married Kendall’s close friend Hailey Bieber (née Baldwin).

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In 2015, Justin suggested that he casually dated Kendall, telling Billboard it was “never serious” between them. 

In response to reports about him and Kourtney early the next year, he jokingly told The Bert Show, “I’m being used man. What can I say? … Nah, we’ll leave it at that.”

Later that year, he was romantically linked to Hailey for the first time, but he ended 2016 with a brief relationship with Sofia Richie.

From 2017-2020, Sofia dated Scott, who was previously in an on-and-off relationship with Kourtney from 2006-2015.

Finally, Justin married Hailey in 2018.