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Celebrity Serial Daters

Erin Demchak Erin Demchak
September 16th, 2008 9:15am EDT
John MayerIn Hollywood, the dating circle seems to be so small that most celebrities share boyfriends and girlfriends and swap spit left and right. The time between significant others seems to get shorter and shorter as well. Last week's tabloid cover may show a huge celebrity breakup and the week after it will feature the same exes and who they're already dating next. And although this isn't the case with all of Hollywood, there are a few we like to call Celebrity Serial Daters.

John Mayer uses his smooth rock star status to make the ladies fall for him, but seems to break their hearts just as fast. He's dated Jennifer Love Hewitt, Jessica Simpson, Cameron Diaz, Minka Kelly and Jennifer Aniston just to name a few.

John Mayer



Sienna Miller is quite the little player herself and loves a good married man. She has been involved with Jude Law, Puff Daddy, James Franco, Matthew Rhys, Rhys Ifans and Balthazar Getty.

Sienna Miller



Derek Jeter is a good player both on and off the baseball field. He goes through women as fast as Amy Winehouse goes a bottle of Jack Daniels. He's had relations with Mariah Carey, Gabrielle Union, Vanessa Minnillo, Minka Kelly, Jessica Alba, Dayanara Torres and Jessica Biel.

Derek Jeter



Jennifer Love Hewitt's body must be a wonderland! Before she was engaged to Ross McCall, she dated half of young Hollywood. She reportedly dated Carson Daly, Andrew Keegan, Will Friedle, Joey Lawrence, Will Estes, Rich Cronin, Wilmer Valderrama, John Mayer and Stephen Dorff.

Jennifer Love Hewitt



Kirsten Dunst may not be the cutest crayon in the box but the boys always seem to pick her first! She's allegedly been involved with Jay Hernandez, Jake Gyllenhaal, Adam Levine, Zach Braff, Andy Samberg, Ryan Gosling and Justin Long.

Kirsten Dunst



Kate Hudson probably tops the list of serial daters. She was off the market for awhile when she was married to Chris Robinson, but she made up for that lost time soon after. She's dated Owen Wilson, Lance Armstrong, Justin Timberlake and Dax Shepard.

Kate Hudson



Cameron Diaz may have been involved with Justin Timberlake for about three years, but she's had her share of men since. She's been with Matt Dillon, Kelly Slater, Criss Angel, Jared Leto, Ed Norton, Robbie Williams, John Mayer, Vincent D'Nofrio, Djimon Hounsou, Bradley Cooper, Gerard Butler and Paul Sculfor.

Cameron Diaz



Kelly Slater loves the ladies as much as her loves to surf. He's reportedly shacked up with Cameron Diaz, Pamela Anderson, Gisele Bundchen and Bar Rafaeli.

Alyssa Milano has been dating for a long time and has dated a lot of boys. She's allegedly been with Kirk Cameron, Jason London, Corey Haim, Scott Wolf, Eric Neis, Justin Timberlake, Mark Wahlberg, Fred Durst and Eric Dane.

Alyssa Milano



Paris Hilton has not only made sex tapes with most boys in Hollywood but she's actually dated them too. She's shacked up with Criss Angel, Benji Madden, Simon Rex, Ryan Gosling, Rick Soloman, Adrian Grenier, John Mayer, Nick Carter, Stavros Niarchos, Paris Latsis, Brandon Davis, Edward Furlong, Deryck Whibley, Jason Shaw, Tom Sizemore, Chad Michael Murray, Matt Leinart, Jack Osbourne, Adam Levine, Fred Durst, Travis Barker and Brody Jenner.

Paris Hilton



Lindsay Lohan doesn't discriminate against either sex and has supposedly dated Wilmer Valderrama, Criss Angel, Aaron Carter, Brent Bolthouse, Brett Ratner, Jared Leto, Harry Morton, Brandon Davis, Jude Law, Courtenay Semel, Calum Best and Samantha Ronson.

Lindsay Lohan



Criss Angel, although still married, also loved to play the field. He's hooked up with Lindsay Lohan, Paris Hilton, Pamela Anderson, Cameron Diaz, Britney Spears and Minnie Driver.

Criss Angel



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Erin Demchak
Story by Erin Demchak

Starpulse contributing writer


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