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15 Celebrities Who Dated Over 50 People (Some Over 1,000!)

Entertainment
15 Celebrities Who Dated Over 50 People (Some Over 1,000!)

Being a celebrity has many advantages, although, stars are not automatically exempt from the day-to-day struggles that common folk deal with. The quest for love is one area where some celebrities shine and others fail. Sure, there are the long-lasting romance stories in Hollywood that prove that love and fame can co-exist, but more often than not, hot love affairs fizzle out within a few years and it’s back on the celebrity dating train.

With so many beautiful people in the industry, limitless funds for dating and going out, it’s no wonder some celebs are serial daters. Many young stars get overwhelmed with the glitz and glamour of Hollywood and want to enjoy the clubs, the social gatherings, and the dating pool of beautiful people. In the age of Instagram, dating apps, and excess, it’s no wonder that some fall into the trap of profusion.

But how many dates are too many? Is there a point where celebrities should take a deep breath and re-evaluate their actions? Is love being suffocated by a hedonistic need for the next best partner? Who are the stars with the most names in their little black books? We’ve dug deep and found the 15 of the biggest serial daters in the entertainment world. Young and old, men and women alike, this list is compiled of some surprising (and some very unsurprising!) offenders. Here are 15 Celebrities Who Have Dated Over 50 People.

15. John Mayer

John Mayer is one of the music industry’s most notorious playboys. Since his music career kicked off in 1998, John has had his fair share of famous girlfriends. Jessica Simpson, Jennifer Love Hewitt, Katy Perry, and Jennifer Aniston have all dated him. He has also been linked to Taylor Swift, Kim Kardashian, Cameron Diaz, and Miley Cyrus. Unfortunately, his reputation with the ladies is not squeaky clean. Many of his exes have accused him of cheating, and his alcohol dependency didn’t help matters of the heart. Things seem to be shaping up for the 40-year-old singer, however. He recently celebrated one year of sobriety, and he seems to be taking a break from dating to focus on his wellness. Maybe this bad boy has found redemption!

14. Taylor Swift

If you count all of the ex-boyfriends in Taylor Swift’s songs, you come up with a number that is probably a conservative estimate of how many she has dated. The pop star has had a slew of famous boyfriends, which include Taylor Lautner, Jake Gyllenhaal, John Mayer, Harry Styles, and Tom Hiddleston. The blonde bombshell is definitely boy crazy, but doesn’t have much luck when it comes to longevity in love. Not one to stay single for long, Taylor has perfected the art of jumping from man to man with very little down time in between relationships. She is currently dating British actor Joe Alwyn, who was introduced to her by pal Emma Stone. Time will tell if Taylor has what it takes to settle into a long-lasting romance or if she’ll keep bouncing around and writing songs about jaded lovers.

13. Colin Farrell

Dreamy Irish actor Colin Farrell has been a long-time favorite amongst the ladies. The reformed bad boy has been linked to Britney Spears, Angelina Jolie, Demi Moore, Paris Hilton, and Lindsay Lohan. The 41-year-old was briefly married to actress Amelia Warner in 2001. They split after 4 months of matrimony; clearly it was not in the stars! Additionally, Colin has two sons with two different women, and he is no longer with either of them. The complexities of his life were only exaggerated by his battle with drugs and alcohol. He went to a rehab clinic in 2005, however, and has been living sober ever since. He has been single for quite some time now, but he still joins the gang of serial daters for his past history!

12. Paris Hilton

Once upon a time, Paris Hilton was the most recognizable and important face in Hollywood. She grazed covers of magazines, appeared on TV shows, and was all over entertainment websites. People were equally interested in her wild outfits as they were with her dating life. She notoriously romanced Benji Madden, Jared Leto, Andy Roddick, DJ AM, Rick Salomon, and Nick Carter. This party girl was switching men almost as quickly as she was switching outfits. These days, she is far less of a big deal in the entertainment world, though, she tries desperately to stay current. She’s slowed down ever so slightly and has been with her boyfriend, River Viiperi, since 2012. That’s definitely a personal record for the heiress.

11. Tommy Lee

Motley Crue frontman Tommy Lee was one of the biggest playboys in rock and roll in the 90s. He was famously married to blonde bombshell Heather Locklear from 1986 to 1993. Locklear put up with close to a decade of Tommy’s wild ways, which included drugs, women, and touring. In 1995, Lee would marry Playboy model and Baywatch star Pamela Anderson after knowing her for a mere 4 days. They had two sons together and split in 1998, only to reunite briefly after Lee was released from prison; he had served 6 months for spousal abuse. The thrice-divorced rocker has also been linked to Shauna Sand, Daisy De La Hoya, Tara Reid, Naomi Campbell, and Carmen Electra. He is currently dating Internet comedian Brittany Furlan.

10. George Clooney

Silver fox George Clooney might be a happily married man, but before he met his wife Amal, he was one of Hollywood’s most famous bachelors. He was married briefly to Talia Balsam, from 1989 to 1993, but in the aftermath of their divorce, he swore he would never marry again. He spent the better part of the next two decades jumping from woman to woman, but never getting too serious. He has dated Charlize Theron, Kelly Preston, Teri Hatcher, Lisa Snowdon, and Stacy Keibler. He definitely had his fair share of dating, but he seems to be in a very good place now. Married to Amal since 2014 (together since 2013), the happy couple have twins, Ella and Alexander.

9. Cameron Diaz

Cameron Diaz is another famed starlet who famously frolicked with quite a few gentleman. The 45-year-old actress got married to Benji Madden in 2015, but before that, her love life was quite colourful. She spent four years with Jared Leto from 1999 to 2003, and then another three years with Justin Timberlake from 2003 to 2006. Her history doesn’t only include long-term relationships, though. She has also been linked to Alex Rodriguez, Adam Levine, Keanu Reeves, Gerard Butler, Bradley Cooper, and surfer Kelly Slater. Prior to getting married, she was rather against the idea of marriage. She referred to matrimony as a “dying institution” that did not serve humanity. I guess that Benji Madden has something really special that made her change her mind!

8. Jennifer Love Hewitt

Jennifer Love Hewitt is no longer at the peak of her acting career, but there was a time when this beauty was the hottest thing. She was boy crazy from the very start. Jennifer would date quite a slew of famous faces before settling into marriage with her hubby Brian Hallisay in 2013. Before she turned in her little black book, she was linked to Jamie Kennedy, John Mayer, John Cusack, Joey Lawrence, Wilmer Valderrama, and Carson Daly. In total, she dated over 25 A-listers, and the total is much higher when you account for the little flings and non-celeb hook-ups! She was definitely busy with the boys, but somehow still managed to have a very successful acting career.

7. Justin Timberlake

As one of the most successful pop singers of all time, it’s no wonder Justin Timberlake had no trouble attracting interesting women to date. From his NSYNC days to now, he has dated many, many famous and beautiful women. He has traded in his playboy ways, though, for a happy family life with his gorgeous wife, Jessica Biel. The two have been together for close to a decade and have one daughter together. Before his Jessica days, Justin dated Britney Spears, Fergie, Jenna Dewan, Alyssa Milano, Cameron Diaz, Scarlett Johansson, and Mila Kunis. He definitely had quite a lot of lady time before he settled into his new role as husband and dad.

6. Leonardo DiCaprio

Oh yes, Leonardo DiCaprio, the man who only dates beautiful swimsuit models, has had quite the luck when it comes to dating. Although, he does seem to play the role of bachelor quite well. At 42 years old, he’s almost like a younger version of George Clooney. However, it’s yet to be determined if he will find his forever love (sadly, it’s not Kate Winslet). His dating repertoire includes Kate Moss, Claire Danes, Alicia Silverstone, Demi Moore, Gisele Bundchen, Paris Hilton, Sienna Miller, and Bar Rafaeli. He is, allegedly, currently dating 23-year-old German model Lorena Rae. This ladies man has definitely had his share of experiences with beautiful and successful women.

5. Charlie Sheen

Charlie Sheen’s life has been a major whirlwind of sex, drugs, and partying. This wild child has experienced extreme living and has struggled with addiction to alcohol, drugs, and women. Nowadays, he is focusing on getting healthy. Since he’s admitted to being HIV-positive, he has tried to get his life on track and rid himself of his crippling dependencies. Before he took charge of his life, he certainly had his fair share of women. The 52-year-old is thrice divorced, with ex-wives including Brooke Mueller, Denise Richards, and Donna Peele. He also dated Kelly Preston, Bree Olson, Stephanie Seymour, Tara Phillips, and Brittany Ashland. He has reportedly been with over 5,000 people intimately, which made the news of him being HIV positive all the more troublesome for his past partners.

4. Jack Nicholson

Jack Nicholson might’ve turned 80 this year, but he effortlessly claims a spot on this list. The self-proclaimed romantic split from his partner of 16 years, Angelica Huston, back in 1990, and subsequently became a serial lover. He has claimed to have been with more than 2,000 women in his prime years, miraculously, only fathering 5 children in that timeframe. He has been linked to (mostly younger) women all over the map. Kate Moss, Paz de la Huerta, Lara Flynn Boyle, and Melanie Griffith are just some of the celebrities that have been romanced by the smooth talker. Sadly, it seems that Jack has retired from women. A few years ago, he discussed his sadness at not attracting women the way he used to. You had a good run, old boy!

3. Simon Cowell

Simon Cowell has had a reputation of being Hollywood’s bully since the beginning of American Idol, back in 2002. His dry and sarcastic sense of humour didn’t keep the women away, however. According to Cowell, he has had over 2,000 lovers. He has been with his girlfriend Lauren Silverman since 2013; their relationship started when she was still married, and the pair ended up having a baby together quite soon after the affair went public, in 2014. Before settling into family life, Cowell has been linked to Carmen Electra, Dannii Minogue, Danielle Delaney, Paula Hamilton, Georgina Law, and Terri Seymour. His cockiness and arrogance might stem from his bedroom stats; he certainly has one of the most active histories in the celebrity world.

2. Gene Simmons

One of the most famous rock’n’ roll bands of all time, Kiss, hosts member Gene Simmons, who has claimed to have had over 5,000 lovers in his very active career. The 68 year-old rocker has been with the same woman, wife Shannon Lee Tweed, for over 28 years. Before meeting Tweed, however, Simmons was busy romancing women at bars and clubs, where his fame made him a natural with the ladies. Prior to kicking off his long-term relationship with Tweed, Simmons had dated Cher, Diana Ross, Katey Sagal, and even Liza Minnelli. Due to his rock-star lifestyle, many of his past lovers are groupies, strippers, and people that he met on the road.

1. Aaron Carter

Lately, Aaron Carter has been making news for his troubles with the law and substance abuse issues. The former golden child hit a bad patch in his 20s and has had a hard time ever since. He claimed bankruptcy in 2013, got arrested several times, and has been trying desperately to re-establish his music career and stay on track. He is currently single, but has amassed quite a list of dating partners over the years. He has been linked to Lindsay Lohan, Hillary Duff, Kaci Brown, Madison Parker, and Kat Stacks. He was also briefly engaged to Maile Hochuli and Kari Ann Peniche, although both of those engagements ended up being called off.

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