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Pete Davidson -

If anyone deserves to be at the top of this list, it's Pete Davidson. The guy dated several major celebs in 2021 alone! He's photographed here on a date with 'Bridgerton' star Phoebe Dynevor, whom he dated for a few months over the summer. In November, it was confirmed that he had started dating Kim Kardashian.

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Pete Davidson -

He was famously engaged to Ariana Grande for five months in 2018. After their breakup, he briefly dated Kate Beckinsale, Margaret Qualley, and Kaia Gerber.

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Taylor Swift -

If you've listened to any of Taylor Swift's songs, then you know she's had a tumultuous dating history! She's been happily partnered up with English actor Joe Alwyn for years, but before that she dated Calvin Harris. The relationship ended in drama and several iconic Swift songs, including ‘I Forgot That You Existed.'

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Taylor Swift -

Before Calvin Harris, Swift dated Joe Jonas, John Mayer, Harry Styles, and Jake Gyllenhaal, to name a few.

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John Mayer -

If anyone could match Taylor Swift in the quantity of exes and nasty breakups, it's John Mayer! They dated for around a year in 2009 when Swift was 19 and Mayer was 32. She wrote the breakup anthem 'Dear John' after their split. Mayer called it "cheap songwriting."

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John Mayer -

Mayer's many exes include Jennifer Love-Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston, and Katy Perry.

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Jennifer Aniston -

Jennifer Aniston has been in and out of the Hollywood dating pool for more than 20 years now! Before her marriage to Brad Pitt, she dated '90s stars Charlie Schlatter, Daniel McDonald, Counting Crows front man Adam Duritz, Tate Donovan (pictured), and Paul Rudd.

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Jennifer Aniston -

In the post-Pitt era, she had relationships with Vince Vaughn, the prolific John Mayer, and finally her second husband Justin Theroux. They split in 2017. 

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Gigi Hadid -

Gigi Hadid was coupled up with Zayn Malik for the past two years until their dramatic breakup in October of 2021. They previously dated from 2015 to 2018. Hadid was linked to 'The Bachelorette’s' Tyler Cameron in between her two stints with Malik.

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Gigi Hadid -

In the past, Hadid has dated Joe Jonas, Cody Simpson, and was rumored to have dated Formula One star Lewis Hamilton for a short time! No doubt she'll be getting back out there with some new famous faces after her breakup from Malik.

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Bradley Cooper -

Bradley Cooper has dated more than his fair share of beautiful, talented women. He has dated Cameron Diaz, Denise Richards, Zoe Saldana, Renée Zellweger, Olivia Wilde, and Jennifer Lopez. He was also married to actress Jennifer Esposito from 2006 to 2007.

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Bradley Cooper -

His longest relationship was with supermodel Irina Shayk. They dated between 2015 and 2019 and even share a daughter. 

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Jennifer Lopez -

Jennifer Lopez has been married three times and was engaged to baseball star Alex Rodriguez before breaking it off in 2021. She then returned to one of her most famous exes to the delight of their fans! She and Ben Affleck reunited in 2021 and are now engaged for the second time. 

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Jennifer Lopez -

Her past romances include P. Diddy, Cris Judd, and Casper Smart, and reportedly Rodrigo Santoro, Bradley Cooper, and Drake.

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Cameron Diaz -

Cameron Diaz has more or less retired from acting and settled into family life with her husband Benji Madden and their daughter, Raddix. Back when she was more involved in the glitz and glamor of Hollywood, she dated many eligible stars. For instance, she dated Jude Law in 2006 after they finished filming 'The Holiday' together.

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Cameron Diaz -

Diaz also dated Matt Dillion, Jared Leto, Edward Norton, Bradley Cooper, Alex Rodriguez, and Justin Timberlake. Not bad!

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Justin Timberlake -

Speaking of Justin Timberlake, the pop star and actor has also had countless high-profile relationships. Timberlake and Britney Spears were the most iconic couple of the decade when they got together in 1999.

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Justin Timberlake -

After Britney Spears, Timberlake dated Fergie, Cameron Diaz, Alyssa Milano, and Jenna Dewan. He was also rumored to have dated Scarlett Johansson after she starred in the music video for his song 'What Goes Around/Comes Around.' He has been married to Jessica Biel since 2012.

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Chris Evans -

In 2021, Chris Evans was seen flirting on TV with Lizzo and was rumored to be dating Selena Gomez. He briefly dated Kate Bosworth way back in 2001, followed by Jessica Biel, and Emmy Rossum.

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Chris Evans -

He later dated Christina Ricci, Kristin Cavallari, Amy Smart, Dianna Agron, Ashley Greene, Sandra Bullock, Jenny Slate, and Lily Collins.

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Madonna -

Madonna has been married twice, first to Sean Penn and then to Guy Ritchie. She divorced Ritchie in 2008 and has been a serial dater ever since! She has been linked to many young men, often dancers and choreographers like Timor Steffens (pictured) and Brahim Zaibat.

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Madonna - When she first moved to New York in the 1980s, she dated the famous artist Jean-Michael Basquiat, followed by actor Warren Beatty in the 1990s.

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Matthew McConaughey -

Matthew McConaughey has been married to Camila Alves since 2006, but before he settled down he dated many famous women. These include Sandra Bullock, Ashley Judd, and Penélope Cruz.

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Drew Barrymore -

Drew Barrymore had two short-lived marriages in the late '90s and early 2000s, back when she was a bit more of a wild child. She was married to Jeremy Thomas for a year when she was 19, and Tom Green for a year when she was 26.

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Drew Barrymore -

Around that time she also dated David Arquette, Luke Wilson, Edward Norton, Spike Jonze, and Sam Rockwell. She married Will Kopelman in 2012 and had two children before separating in 2016. She's still good friends with many of her exes!

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George Clooney -

George Clooney dated Kelly Preston in 1988 before marrying actress Talia Balsam in 1989. The relationship lasted for three years before they divorced, and Clooney moved on to Kimberly Russell, Celine Balitran, and Krista Allen. 

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George Clooney -

He was rumored to date Renée Zellweger after they filmed 'Leatherheads' in 2008. He had several more short-lived relationships with various actresses and models before meeting Amal Alamuddin, the amazing woman who has been his wife since 2014.

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Cara Delevingne - Cara Delevingne has dated both men and women from all over the world and from various areas of the entertainment industry. In the past, she has been linked to Paris Jackson, St. Vincent, actress Michelle Rodriguez, Miley Cyrus, and British singer Jake Bugg.

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Cara Delevingne -

Her most recent confirmed relationship was with 'Pretty Little Liars' star Ashley Benson. They dated for approximately two years before breaking up in April 2020.

Sources: (TheThings) (Cafe Mom)

See also: Every famous woman Cara Delevingne has dated (or been rumored to date)

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