They Get Around: 15 Celebrities Who Are Serial Daters (Taylor Swift ain't the only one!)

They Get Around: 15 Celebrities Who Are Serial Daters (Taylor Swift ain’t the only one!)

News of a Hollywood relationship gets around almost as fast as the celebrities on this list do. They took casual dating to a whole other level.

Check out these 15 celebs who are serial daters! Taylor Swift ain’t the only one!

Lil Wayne


Lil Wayne has so many baby mamas they could start their own reality show. In addition to Nivea, Lauren London, Toya Wright and Sarah Bellew who are the mothers of his 4 children, Lil Wayne also dated rapper Trina (whom he also impregnated but had a miscarriage), Karrine Stephens (a video vixen and best selling author who also dated Bill Maher), hip-hop model Tammy Torres, and singer Shanell.


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We all know from her music that Rih Rih likes to get down with the dudes. Those dudes happened to be Shia Labeuf, Josh Harnett, Chris Brown, Drake, Andrew Bynom, and Matt Kemp.

John Mayer

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While most people who date around seem to do so out of fun, John Mayer seems to date strictly to avoid his inevitable boredom. Women seem to fall for his bad boy, brooding, broken, nonchalant rockstar routine but often end up hurt by the very same thing.  Mayer has made of a show of many of his relationships with Hollywood starlets which include Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Jennifer Aniston, Minka Kelly, Taylor Swift, and now Katy Perry.

Joe Jonas


The 23-year-old cutie has made quite a reputation for himself being a bit of a ladies man aka player. Joe has dated singer/actress AJ Michalka, Taylor Swift whom he broke up with over the phone to be with actress Camilla Belle, Demi Lovato, Twilight‘s Ashley Greene, Extra correspondent Renee Bargh, model Elizabeth Zayas, and former model turned graphic designer Blanda Eggenschwiler. Not to mention all the “rumored” romances that we won’t mention.

Taylor Swift

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Photo: WENN

The phrase, “you can’t play a player” usually rings true, except in Taylor Swift’s case when it came to at least two of her former flames. Swift is a serial dater who dated serial daters Joe Jonas and John Mayer, both of whom ditched her for someone else. Still, Taylor is probably the most popular serial dater in Hollywood right now. In addition to Joe Jonas and John Mayer, she’s dated Jake Gyllenhaal, Taylor Lautner, Conor Kennedy (yes the Kennedy family), Glee’s Cory Monteith, actor Toby Hemingway (The Covenant), and most recently Harry Styles from One Direction. And once again we’re not even counting a host of rumored flings that include Patrick Schwarzenegger, Tim Tebow, and Tron Legacy‘s lead Garrett Hedlund. That’s us not counting them.

Amber Rose

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Photo: DJDM /

Amber Rose suddenly appeared out of nowhere a few years ago and became famous for…dating celebrities?  We’re not really sure, but the former video vixen has shared a romance with Kanye West, obscure rapper Ryan Banks, Reggie Bush, Amar’e Stoudemire, Fabolous, and Chris Brown but Wiz Khalifa is the only one to be able to call Amber his baby mama.


Justin Timberlake

Justin Timberlake

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JT is mostly a long-term kind of guy but he’s gotten around a bit in Hollywood, too. Three years before Justin dated Britney he dated Stacy Ferguson better known as “Fergie.” After the very high-profile relationship with first love Britney Spears, Justin went on to date his backup dancer Jenna Dewan (now wife of Channing Tatum), Alyssa Milano, Cameron Diaz, and of course Jessica Biel but he was also linked to Olivia Munn, Janet Jackson, Ciara, Rihanna, and Olivia Wilde. No word on if there is any truth to those rumors, though.

Wilmer Valderama

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Judy Eddy/

Valderama has a thing for  young White celebs, sometimes of the troubled variety. The actor of That 70’s Show fame  has dated Jennifer Love Hewitt, Mandy Moore, Lindsay Lohan, Ashley Simpson, Avril Lavigne, Demi Lovato, and Minka Kelly.

P. Diddy

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Photo: Steve Granitz/WireImage

Cassie may be Diddy’s official girl now but he’s had quite a few others along the way. The music mogul has dated Karrine Stephens (a video vixen and best selling author who also dated Bill Maher and Lil Wayne), Jennifer Lopez, Lil Kim, Naomi Campbell, Sienna Miller, and rumored to have had a fling with Cameron Diaz. And let’s not forget Diddy’s other official girl Kim Porter.

 Nick Jonas


Nick has taken after big bro Joe in the dating department. Serial dating the likes of Miley Cyrus–who was his first love–, Singer Jordan Pruitt (of Disney fame), Selena Gomez, Australian singer-songrwriter/actress Delta Gooderm (8 years his senior), Model Gigi Hadid (a Real Houswives of Beverly Hills’ daughter), and actress/singer Samantha Barks.

Derek Jeter

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Jeter is a player both on and off the field. The baseball star used to date Mariah Carey, Gabrielle Union, Vanessa Minnillo, Minka Kelly, Jessica Alba, Jordana Brewster, Joy Enriquez and Jessica Biel. Andd you thought A-Rod was bad…

Ryan Gosling

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Photo: Ian Wilson/

Ryan Gosling can do no wrong, so if Ryan wants to date, he can date! And we don’t think anything of it. Ryan’s list of lovers includes Sandra Bullock, Rachel McAdams, Olivia Wilde, Kat Dennings, Blake Lively, and most recently Eva Mendes–yeah, that last one is odd to us, too.

50 Cent

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Photo: WENN

50 Cent doesn’t exactly seem like a ladies man (like  Joe Jonas) or a man-ho (like John Mayer) but he sure gets around. The rapper has been romantically involved with Vivica Fox, Ciara, Khloe Kardashian, Chelsea Handler, Elise Neal, Paris Hilton, and Tahiry Jose.

Leonardo DiCaprio

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Photo: WENN

Leo has a thing for supermodels from Naomi Campbell (1995) to Gisele Bündchen, to Bar Rafaeli, and Erin Heatherton but he doesn’t leave out the actresses altogether. DiCaprio has dated Kidada Jones (Quincy Jones’ daughter once engaged to Tupac), Blake Lively, and had a host of “rumored” romances with actresses from Demi Moore to Linsday Lohan.

George Clooney

George Clooney PF WENN

Photo: WENN

Clooney is the quintessence of a terminal bachelor. While he has an extensive list of romances, most are with women who only came to prominence with dating him. His Hollywood flames include Karen Duffy,Traylor Howard, Krista Allen, and Stacy Keibler. And since the 51-year-old actor says he’s never getting married again, he has the rest of his life to play the field. For better…or for worse.

  • momofthree

    I think some of these male “serial daters” are in the closet which is the reason they won’t commit to a woman.

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