Celebrities Who Have Dated The Same People – Taylor Swift Has Shared Boyfriends With Katy Perry & Selena Gomez

Burtland Dixon | November 20, 2024 3:00 pm

Being a celebrity means you have an increased chance of dating someone that another celeb already dated. It's pretty commonplace, but it still can get tricky at times. Here are some celebs that share exes. Are any of these a surprise?

Big Sean And Pete Davidson Mingled With Ariana Grande

big sean, arianna grande, pete davidson
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Photo Credit: Jason Merritt/TERM / Staff / Bobby Bank / Contributor / Getty Images

All three stars here have a pretty lovely dating history with other celebrities, so the crossover was inevitable.

Big Sean and Ariana Grande dated in 2014 for some time. They lasted for eight months. Skete Davidson, or Pete, got with her in 2018 after her previous ex, Mac Miller.

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John Mayer Is Swift With Katy Perry

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katy perry, john mayer, taylor swift
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Photo Credit: Christopher Polk / Staff / Mark Metcalfe / Stringer
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John Mayer clearly likes dating musicians. He and Taylor Swift first connected on Twitter and collaborated on a song in 2009. They would go on to date until 2010.

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After her, he ended up with Katy Perry in 2012. Unfortunately, they broke things off in 2013, one month after engagement rumors started to swirl.

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All The Love For Selena Gomez

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Justin Bieber, Selena Gomez, The Weeknd
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Photo Credit: Kevin Mazur / Contributor / Christopher Polk / Staff / Getty Images
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Have you ever wondered why The Weeknd and Justin Bieber haven't made a song together yet? Let's just say Selena Gomez has something to do with it.

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Bieber was with her first in 2009. Then, The Weeknd dated her almost as a rebound after a short split with Bella Hadid in 2017.

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Sandra Bullock Knows What She Likes

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Matthew McConaughey
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Photo Credit: Stephane Cardinale - Corbis / Contributor / Vivien Killilea / Stringer / Getty Images
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Sandra Bullock met Ryan Gosling and Matthew McConaughey on separate movie sets and ended up with both of them.

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McConaughey was first, in '96 through '98. Gosling came along in 2002 and lasted until 2003.

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Lisa Bonet Must Like Men With Long Hair

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Lenny Kravitz, Jason Momoa, Lisa Bonet
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Photo Credit: Dimitrios Kambouris / Staff / Vinnie Zuffante / Contributor / Getty Images
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Before Jason Momoa came on the scene, Lisa Bonet and Lenny Kravitz eloped in the mid-'80s. They went on to have a kid but divorced in '93.

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Some years later (2017), she married Momoa. Sadly, those two announced their split in 2022.

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They Both Lost A Kardashian

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Kanye west, Ray J, Kim Kardashian
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Photo Credit: Frederick M. Brown / Stringer / Rodin Eckenroth / Taylor Hill / Contributor
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According to Ray J, he had Kim Kardashian first. They released a "special" video together in 2007 to commemorate their love.

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Fast forward to 2011 when Ye and the most famous Kardashian began dating. None of them have her now.

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Scandal? Angelina Jolie, Jennifer Aniston, And Brad Pitt

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Angelina Jolie, Brad Pitt and Jennifer Aniston
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James Quinton/WireImage
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Do you remember this wild scandal? While married to Jennifer Aniston, Brad Pitt met Angelina Jolie on the set of Mr. & Mrs. Smith.

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Aniston quickly filed for divorce after Pitt met Jolie, before the new couple married in 2014. We all know how that one ended.

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Miley Cyrus Plays For Both Sides

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Miley Cyrus,
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Photo Credit: Alberto E. Rodriguez / Staff / Robert Kamau / Contributor / Getty Images
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It was like fans witnessed Miley Cyrus break Liam Hemsworth right before their eyes. It was a tough 2020 for Hemsworth after they split.

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The same day outlets revealed the Cyrus and Hemsworth break, there were already photos of Cyrus kissing Kaitlynn Carter (Brody Jenner's ex). It wasn't until the end of that month they said they were better off as friends.

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Early 2000s Romances For Taylor Swift

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Jake Gyllenhaal Taylor swift and John Mayer
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Photo Credit: Brendon Thorne / Stringer / Dimitrios Kambouris / Staff / Getty Images
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Jake Gyllenhaal dated Taylor Swift for all of two months and broke up with her right before New Year's 2010.

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She and John Mayer ended things because of a huge age gap. She was only 19 when they started dating in 2009. He was 32.

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Johnny Depp Was The Biggest Heart-Throb

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Winona Ryder, Johnny Depp, Kate Moss
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Barry King / Contributor / Getty Images /
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Johnny Depp used to be one of the most beloved men in Hollywood. He and Winona Ryder got engaged in 1990, but would part ways in '94 due to the media pressure.

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Depp met Kate Moss in '94 as well, and they would quickly begin seeing each other. They lasted a year shorter, ending things in '97.

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It's Hard To Resist An Avenger

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Scarlett Johansson Reynolds
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Photo Credit: Kevin Mazur / Contributor / Getty Images
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There are plenty of Hollywood stars who would love to date Scarlett Johansson. She and Jared Leto had a brief fling in 2004.

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Things were much deeper with Ryan Reynolds. After two years of marriage, they called it off. "We entered our relationship with love, and it's with love and kindness that we leave it," they said in a joint statement.

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Seal Loves Supermodels

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Seal and heidi Klum and Tyra Banks
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Seal dated Tyra Banks in 1996 for nine months. He was 32 and she was 22 as they moved under the radar.

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Eight years after Banks, he and Heidi Klum got engaged on a glacier. They remained married from 2005 to 2014 and share four children.

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Can't Get Enough Of Bella Hadid

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Weeknd Bella hadid and Drake
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Photo Credit: Samir Hussein / Contributor / Frazer Harrison / Staff / Getty Images
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Bella Hadid is The Weeknd's ultimate muse. He temporarily dated Selena Gomez but would get back with Hadid before eventually calling it quits in 2021.

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Drake is borderline sneaky with who he dates. His fling with Hadid was very short.

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Jaden Smith Saw The Potential In Kylie

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Jaden smith, Tyga, Kylie Jenner
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If fans remember correctly, Jaden Smith was the first high-profile person Kylie Jenner dated. They were both still pups then, but it counts.

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After him, she got with Tyga, who had to wait to make a move because she wasn't 18 yet. Tyga and Jenner would last a long time before she moved on to Travis Scott.

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Demi More Doesn't Really Have A Type

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GettyImages-Ashton Kutcher & Bruce Willis
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Photo Credit: Chris Weeks/WireImage
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Demi Moore met Bruce Willis in 1987 at a movie premiere and they eloped two months later. Three daughters later, they split in 1998.

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In 2003, Ashton Kutcher was her next man as they married in 2005. Their divorce came in 2013.

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Kendall Jenner Loves Athletes

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Photo Credit: Neilson Barnard / Staff / James Devaney / Contributor / Getty Images
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If you look at Kendall Jenner's dating history, there are plenty of basketball players on that list.

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First, there was Blake Griffin from 2018 to 2019. Shortly after, she fell for Ben Simmons.