12 Celebs Who've Dated A Shockingly High Number Of People

Hollywood’s serial daters have always been unabashedly open about their relationships and longevities (or lack thereof) of those relationships, and are of course seriously unconcerned with the shortness of their bounce back times, too. While some may be surprisingly circumspect regarding the reasons for their breakups, others are openly vile in their public accusations and insinuations.

We all enjoy knowing about who’s dating our favorite stars, and of course, who has dumped whom. Thanks to the paparazzi or certain legit sections of the media, Hollywood relationships are always reported on, so our missing out on something totally is quite rare. Of course, the worldwide interest in celebrity relationships also helps in this regard.

Yet, while Hollywood is notorious for short (really short) relationships, there are a few players that are flag bearers for even faster rebounds. The following 10 A list celebrities are the official serial daters of the industry, having reportedly dated a shockingly high number of people! Some of them are truly surprise entrants on the list, considering that they never appeared the type to go on serial dating sprees. Others that are on here are of course completely expected, as in anyone could have guessed that!


12 Cameron Diaz

Most men would gladly accept and love to date the hot and happening actress, model Cameron Diaz. Others might not be so open about expressing these wishes but they’d never pass up on the opportunity for sure, should it ever present itself. Hollywood actors seem to feel the same, for the glamorous damsel has gone through them like a packet of Lay’s chips. From Carlos De La Torre, to Matt Damon, A-Rod, Justin Timberlake and Paul Sculfor, the actress has sure shown an eclectic taste in her men! She’s reportedly also been involved with Criss Angel, Robbie Williams, Jared Leto, Gerard Butler, Bradley Cooper and a list that goes on and on.

11 Taylor Swift


Soulful love songs might indeed be Taylor Swift’s thing, but another thing that goes hand in hand with her famous name is a list containing a long string of stars that she’s dated. Her list of elite exes contains names like John Mayer, Jake Gyllenhaal, Taylor Lautner, Joe Jonas, Harry Styles and Conor Kennedy. She’s recently been spotted hand in hand with her (reportedly) current flame, DJ Calvin Harris. It seems that while the singer may be crooning about her love, she is actually quite the heartbreaker.

10 George Clooney

Considering George Clooney’s enviable list of stars that he’s dated after his marriage to Talia Balsam ended, it seemed that the star was using relationships as therapy (and we would never again see him at the altar taking new vows again). Yet, now that the actor has settled down with hotshot lawyer Amal Alamuddin, we can safely put the ghosts of his past girlfriends to rest. Of course, an elite list that contains names such as Kelly Preston, Krista Allen, Teri Hatcher, Lucy Liu, Elisabetta Canalis and Lisa Snowden (to name just as few) can hardly be put totally to rest.

9 Sienna Miller


Golden haired actress Sienna Miller, seems to have quite a few handsome notches on her dating history post. Starting from 2001, Sienna has had over 14 public relationships which include with high flying celebs such as Jamie Dornan (of the recent Fifty Shades of Grey fame), Orlando Bloom, Mark Hildebrandt, Daniel Craig, Jude Law, Nico Malleville, Hayden Christensen, James Franco, Sean Combs, Josh Hartnett, Matthew Rhys, Balthazar Getty, Tom Sturridge, George Barker and even Puff Daddy.

8 Kate Hudson

This one might be one of those surprising entries. Though Kate Hudson was no longer actively playing the dating field while being married to Chris Robinson, she covered a lot of distance once that was officially over. Her real long list of ‘loved and then discarded’ celebs include Lance Armstrong, Owen Wilson, Justin Timberlake, Dax Shepard, Chris Robinson, Baron Davis, Shannon Leto, Heath Ledger, Adam Scott, Matthew Bellamy, Darren Ankenman and Alex Rodriguez, to name a few.

7 John Mayer


Being a rock star grants special statuses and one of them is that privilege of loving people and then breaking their hearts (unintentionally, of course). This smooth operator has previously dated stunning beauties like Jennifer Love Hewitt, Jennifer Aniston, Cameron Diaz, Jessica Simpson, Minka Kelly, Vanessa Carlton, Rhona Mitra, Milana Vayntrub, Taylor Swift, Scheana Marie, Katy Perry and Reena Hammer. Needless to say, he must definitely know his way with words and charming the ladies.

6 Jennifer Love Hewitt

Beautiful actress Jennifer Love Hewitt is a self-proclaimed ‘love-aholic’. Though the actress is currently involved with Brian Hallisay, Jennifer has played the field with Ross McCall, Will Estes, Stephen Dorff, Joey Lawrence, Will Friedle, Andrew Keegan, Carson Daly, Ricj Cronin, John Mayer, Wilmer Valderrama, Fred Savage, Joseph Lawrence, Jason Aaron Baca, Diego Serrano, Enrique Iglesias (rumored), John Cusack, Antonio Sabato Jr., etc. With a list this long, how on earth did she ever have time to focus on her acting career?


5 Paris Hilton


Partying, riches, booze and sex tapes are not the only things Paris Hilton is notorious for. The lady it seems has notched up another title and that is of being a ‘serial dater’; after she’s reportedly dated what seems like half of Hollywood. In her list of ‘people I have dated and dumped’ are names such as Criss Angel, Ryan Gosling, John Mayer, Brody Jenner, Chad Michael Murray, Paris Latsis, Adrian Grenier, Jack Osbourne, Tom Sizemore, Rick Solomon, Matt Leinart, Travis Barker, Brandon Davis, Benji Madden, Jason Shaw, Simon Rex, Nick Carter, Deryck Whibley, Stavros Shaw, Adam Levine, Fred Durst and Stavros Niarchos.

4 Justin Timberlake

Hit singer Justin Timberlake may have settled down with his long time boo Jessica Biel, but his previous list of conquests is just as long and eye-catching as some of the others on this list. From Lindsay Lohan and Beyonce Knowles, to Fergie, Daniella Ditoo, Britney Spears and Alicia Keys, Justin has had a love history with ‘em all. Others on the list include Veronica Finn, Tonya Mitchell, Nicole Appleton, Alyssa Milano, Jenna Dewan Tatum, Emma Bunton, Staci Flood, Cameron Diaz, Tatyana Ali, Scarlett Johansson, Rihanna, Olivia Wilde, Olivia Munn, Thaila Ayala and Kate Hudson, to name a few more.

3 Kirsten Dunst


Another rather surprising entry on this list is Kirsten Dunst. You either love her or simply can’t tolerate her at all, but such opinion polarities don’t seem to have hindered her in any way from making several interesting love conquests. She has been rumored to have been with a whole list of celebrities, including Ryan Gosling, Jay Hernandez, Zach Braff, Adam Levine, Justin Long, Jake Gyllenhaal, Jake Hoffman, Tobey Maguire, Ben Foster, Adam Brody, Johnny Borrell, Fabrizio Moretti, Jason Boesel, Jacob Soboroff and Garrett Hedlund.

2 Alyssa Milano

Alyssa Milano started young when it comes to dating, and hence her dating history is stretched out over the years to contain several male conquests. Having dated a lot of boys, her list extends to Mark Wahlberg, Justin Timberlake, Kirk Cameron, Fred Durst, Jason London, Eric Dane, Corey Haim, Scott Wolf, Eric Neis, Corey Feldman, Wayne McBean, Jonathan Silverman, David Arquette, Scott Wolf, Jason Behr, Cinjun Tate, Brian Krause, Greg Vaughan, Josh Shambaugh, Jimmy Federico, Barry Zito, Carl Pavano, Brad Penny and Dave Bugliari.

1 Leonardo DiCaprio


Leonardo DiCaprio is the original topper on our list of serial daters, for he too has dated a shockingly high number of actresses. His list includes totally awesome names such as Naomi Campbell, Gisele Bundchen, Bar Rafaeli, Blake Lively, Trishelle Cannatella, Bridget Hall, Natasha Henstridge, Kristen Zang, Vanessa Trump, Demi Moore, Kidada Jones, Amber Valletta, Paris Hilton, Erin Heatherton, Kelly Baugher, Alesia Riabenkova, Miranda Kerr, Rihanna, Toni Garrn and Katie Cleary.



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