13 Celebrities Who Surprisingly Dated People

Dating in Hollywood, the expiration date of relationships seems much shorter than in our own boring realities. Celebrities have short and torrid affairs with each other, you think they’re going to get married, and then they move onto the next. Here are the worst serial daters of Hollywood!

 

 

1. Cameron Diaz
This blonde bombshell has dated a fair share of Hollywood hotties, including Justin Timberlake, Matt Damon, Bradley Cooper, Jared Leto, and Gerrard Butler. She’s not biased to just actors though! She dated magician Criss Angel and athlete A-Rod too.

 

 

2. George Clooney
This guy is known to be a womanizer – but who wouldn’t want to be womanized by him? Before settling down with his goddess Amal, he spent time with the likes of Teri Hatcher, Kelly Preston, Lucy Liu, and Stacy Kiebler, amongst others.

3. Taylor Swift
Taylor the heartbreaker has been known to turn her heartbreak into hit records. Her scorned lovers include fellow teeny boppers Harry Styles and Joe Jonas along with Jake Gyllenhaal, Taylor Lautner, John Mayer, and most recently Calvin Harris. Muses, am I right?

4. Ciara
An R&B goddess has to kiss some frogs before she finds her Prince Charming (super fine Russell Wilson). For Ciara, those were 50 cent, Trey Songz, Bow Wow, and Future.

 

 

5. Madonna
An 80’s pop star with some torrid love affairs, including that notorious one with Sean Penn. She also bedded Guy Ritchie, Alex Rodriguez, Warren Beaty, and Vanilla Ice (we know.) We all make mistakes, Madonna.

6. Johnny Depp
This once-babe is on our naughty list this Christmas for messing with most recent ex Amber Heard, but his Hollywood GF track record is generally pretty impressive. Supermodel Kate Moss and him were a famous thing, and same with Juliette Lewis, Vanessa Paradis, and Winona Ryder. Wino 4ever.

7. John Cusack
The “High Fidelity” star ain’t got no type! He dated a lot of ‘90s baes, including Rebecca Romijn, Minnie Driver, Lili Taylor and Neve Campbell. Ugh, so much ‘90s nostalgia for all these couples.

 

 

8. Justin Timberlake
The ladies Justin has hung out with are of a surprising range – this guy really gets around. He dated Lindsay Lohan (pre breakdown), Beyonce (should have held on to that one), Fergie, Britney Spears (denim on denim memories), Alicia Keys, and Olivia Munn. Dang, Jessica Biel must be one confident gal!

9. Leo Dicaprio
If you can believe it, Leo once dated Naomi Campbell. We’re just gonna assume that she dumped him on this one. He also was with Gisele Bundchen for a while, then hanging with a younger model Blake Lively. He’s also dated Demi Moore, Paris Hilton, Rihanna, and Miranda Kerr (three VS angels! Leo, you got a type.)

10. John Mayer
This guy is a notorious player in Hollywood. He’s spent time with Jen Anniston, Katy Perry, Jessica Simpson (that one makes us feel old), Vanessa Carlton, Jennifer Love Hewitt, and Taylor Swift.

 

 

11. Kate Hudson
The carefree California daughter of Goldie Hawn has a lot of notches on her belt, from a lot of serious hotties. We would not be ashamed of this track record. Let’s start with the gorgeous Heath Ledger, RIP. Then she dated Lance Armstrong, funnyman Owen Wilson, Adam Scott, Matthew Bellamy, Chris Robinson, Justin Timberlake and once again, A-Rod. Jeez, these actresses love baseball players!

12. Paris Hilton
“The Simple Life” star and heiress has had arm candy like Adam Levine (we’re pretty jealous of that one) Chad Michael Murray (teenage girl inside of us screaming), mega-hunk Adrien Grenier, Brody Jenner, John Mayer, and Ryan Gosling. If we knew looking like Paris Hilton would get us this far ahead, we would have been rocking frosty pink gloss and a chihuahua years ago.

 

 

13. Alyssa Milano
This star isn’t super relevant in 2016, but her list is impressive enough to garner her a spot on ours. Mark Wahlberg, Kirk Cameron, Fred Durst (ugh), Corey Haim (and Corey Feldman!), Jason London and Justin Timberlake! She really is “Charmed”. Sorry, we had to!