It's so much fun to speculate about celebrity romances, but it's a given that relationships made in Hollywood don't always have the longest staying power. After all, dating as the world watches (and weighs in) can't be easy. So it totally makes sense that celebs end up in a number of short relationships rather than just a couple of long ones, and that tends to leave room for quite a few serial daters among the A-list crowd. It is what it is!
It doesn't have to be a negative thing, though. Dating around means truly figuring out what you want in a long-term partner, right? And these celebs — who include Justin Timberlake and Katy Perry — have definitely tested out the waters in that regard. There's no shame in it, and they've definitely seemed to be having fun! That said, some celeb relationships — Taylor Swift and John Mayer for example — definitely end with a bit of Hollywood drama.
Read on for the most prolific serial daters in Hollywood. Though some of them have since settled down, gotten married, and started families after sowing their wild oats, their hookup histories are seriously impressive and will probably never be forgotten.
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Harry Styles
Harry has so much swagger it's no surprise he's made his rounds with the ladies. The thing is, he also comes off as just really sweet and compassionate. Not exactly a player, but he still gets all the ladies, including Olivia Wilde, Kendall Jenner, Emily Ratajkowski, and of course, Taylor Swift herself.
Leonardo DiCaprio
Leonardo DiCaprio's dating history is extensive — especially when it comes to supermodels, who seem to be his type. He has history with models including Naomi Campbell and Gisele Bündchen, and he even had flings with megastars such as Blake Lively and Rihanna in the past. At one point, he seemed to have settled down with Camila Morrone, but recently, he was spotted hanging with Gigi Hadid.
John Mayer
It's easy to see how John Mayer has managed to snag so many ladies — not only is he good looking, but have you heard his voice? He's been in relationships with everyone from Taylor Swift and Jennifer Aniston to Katy Perry and Jessica Simpson. The list goes on and on …
Pete Davidson
It's like as soon as Pete Davidson started dating Ariana Grande, suddenly he became a total hot commodity in Hollywood. Though their engagement didn't last, it wasn't long before he was spotted with women including Kate Beckinsale and Bridgerton star Phoebe Dynevor. And then, of course, there was his whirlwind relationship with Kim Kardashian.
Chris Evans
Lizzo isn't the only one with a major crush on Captain America! Though his full dating history hasn't been confirmed, Chris Evans has been in long-term relationships with stars including Jessica Biel and Jenny Slate, and had reported romances with Kate Bosworth, Emmy Rossum, Kristin Cavallari, and more.
Cameron Diaz
These days, Cameron Diaz has settled down with Benji Madden, but that wasn't always the case. Before she was keeping it low-key, her exes included Justin Timberlake, Alex Rodriguez, Matt Dillon, and Jared Leto, just to name a few of her most high-profile hookups.
Jennifer Lopez
Sure, we're all head over heels for Jennifer Lopez and Ben Affleck's reunion, but let's not forget that J.Lo's been engaged a whopping five times: to Ben, Alex Rodriguez, Marc Anthony, Ojani Noa, and Cris Judd. And that's not counting her other flings and relationships with stars including Diddy and Casper Smart. She finally wed Ben Affleck in 2022, wihch was her fourth marriage.
Channing Tatum
Before Channing Tatum's marriage to Jenna Dewan, he was rumored to be dating Amanda Bynes, his costar from She's the Man. Then after his divorce, he quickly moved on to date Jessie J, and though that relationship ultimately didn't work out, he's recently been linked to Zoë Kravitz. Who's next, Channing?
Justin Timberlake
Today, Justin Timberlake seems happily settled down with wife Jessica Biel, but it was a roller coaster getting there! He famously dated Britney Spears in his boy band days, followed by high-profile relationships with Jenna Dewan, Cameron Diaz, and Alyssa Milano.
George Clooney
Before he married Amal Alamuddin in 2014, we had a feeling that George Clooney would be a bachelor forever. He was once married to Talia Balsam and has dated fellow celebrities including Lisa Snowdon, Stacy Keibler, Kelly Preston, and Krista Allen.
Scarlett Johansson
It seems like Scarlett Johansson's heart is now set on Colin Jost (especially now that they've welcomed their first child together), but she's had a pretty storied dating history before this. She was married to Ryan Reynolds and then to Romain Dauriac, and she's been linked to Jared Leto, Sean Penn, and Josh Hartnett in the past.
Drew Barrymore
Drew Barrymore has a few marriages under her belt — to Jeremy Thomas, Tom Green, and Will Kopelman, though it seems like she might be single these days. She's also dated Justin Long, Spike Jonze, Luke Wilson, and Edward Norton, among other Hollywood men.
Katy Perry
Katy Perry is now living happily ever after with fiancé Orlando Bloom and their daughter, Daisy Dove, but before that? Well, besides her short-lived marriage to Russell Brand, Katy's dating history includes the likes of John Mayer, Travis McCoy, and Diplo.
Bradley Cooper
With a face like that, of course Bradley Cooper is a serial dater. Since his split from Irina Shayk, he's been rumored to have dated Jennifer Garner and Lady Gaga. And before Irina? Well, there are his relationships with Renée Zellweger, Jennifer Lopez, Zoe Saldana, Suki Waterhouse …
Taylor Swift
Taylor Swift gets a bad rep for her dating history, despite the fact that she was actually settled down with Joe Alwyn for years. But before that, she was linked to stars including John Mayer (whom she keeps penning songs about), Joe Jonas, Jake Gyllenhaal, Tom Hiddleston, Harry Styles, and Calvin Harris. And immediately after her split with Alwyn, she was linked to singer Matty Healy.
Matthew McConaughey
Before Matthew McConaughey met Camila Alves in 2006, he had a pretty impressive dating record. Matthew ended up with girlfriends who shared his huge star power, dating women including Sandra Bullock, Ashley Judd, and Penélope Cruz.
