Some people just love the feeling of love. Some people love being treated to dates. Some people love treating others to dates. And some people go through so many god damn lovers in their lives it’s hard to keep track. These are the people we like to call “serial daters.” We all know one, and if you don’t think you do you’re wrong because we see them all the time on magazine stands on television and on the internet. Celebrities have got to be the worst offenders when it comes to serial dating and who can blame them? True love can he hard to find, and even harder if you’re in the public eye or perhaps dealing with man-eating or womanizing egocentric fellow celebs as lovers.
Hollywood relationships are no rarity, but successful Hollywood relationships? That’s a different story. Dating in general can be pretty complicated for anyone, but imagine having every bit of every relationship you’ve ever had out in the media for everyone to see. It could be a long-term relationship, it could be a fling or it could only be one measly date, but if a celebrity is involved it’s a big deal to Hollywood gossip hounds. Not everyone can find true love on the first try, or the second…or the tenth apparently in some cases. There are tons of fish in the sea they say and perhaps the following celebs just enjoy the catch and release. Here is our list of the 10 most infamous celebrity serial daters.
10 Gigi Hadid
At the tender age of 21, I think it’s safe to call Gigi Hadid a serial dater in training. Since stepping onto the scene in around 2011, she has only had three high-profile love interests. However, like any good serial-dater they all seem to be one right after the other.
Hadid’s first and longest noteworthy relationship was with Australian singer Cody Simpson from 2013-2015. After that she moved onto Joe Jonas whom she later split with after only five months of dating. It wasn’t long until Gigi found new love with Zayn Malik (who looks creepily similar to Joe Jonas). Gigi and Zayn have been on-again-off-again for about eight months now.
9 Jennifer Aniston
At some time or another we have all felt for Jen Aniston. Back in 1998 when she married Brad Pitt the two seemed perfect together. However, in 2005 the marriage came to an end when Brad had an affair with Angelina Jolie. This heartbreak sent Jen on a serial dating spree.
The spree began when Jen dated her The Break Up co-star, Vince Vaughn. When that ended after a year, she went the bad boy route and started dating John Mayer (who obviously made our list too). That came to an end and Jen had a brief secretive hookup with Gerard Butler. A few flings later she finally found true love in 2011 with her now husband Justin Theroux. Like Mom always said, “Sometimes you have to kiss a few frogs to find a prince.”
8 George Clooney
George Clooney, the serial dating expert. As one of Hollywood’s hunkiest and most eligible bachelors for over 22 years, he is a master of the craft usually leaving mere months between each of his relationships. Some of Clooney’s more well-known lovers include Kelly Preston, Lucy Liu and Stacey Keibler. However, added to his list of lovers is a whole slew of lesser known actresses and models including ex-wife Talia Balsam, and former girlfriends Lisa Snowdon, Krista Allen, Sarah Larson, Elisabetta Canalis — the list goes on.
Thankfully, the heartbreaker retired the dating scene when he married Amal Alamuddin in 2014. The two got hitched after less than a year of dating which means Amal must be one special woman for George to put a ring on it that fast. Let’s hope the two live happily ever after.
7 Khloe Kardashian
Another woman we can’t help but feel for is Khloe Kardashian. She seemed to find true love back in 2009 with NBA player Lamar Odom whom she married after a month of dating. Unfortunately, the two called in quits back in 2013 when some of Odom’s demons of substance abuse and infidelity came to light. After losing the love of her life Khloe found her way back to the dating scene and has had fling after fling.
Rapper The Game was rumoured to be one of Khloe’s first post-Lamar rebounds. After him, she dated rapper French Montanna. The two apparently split because she wasn’t ready for how serious the relationship was getting after Lamar. Going back into the NBA world, Khloe then dated player James Harden. She is now rumoured to be dating NFL player Odell Beckham Jr.
Khloe’s constant relationship jumping might have something to do with the fact she’s still incredibly close with her ex-husband. She’s never been shy about announcing the love she still has for him and he is still a solid member of the Kardashian clan. Any of her new boyfriends will have to put up with the fact that Lamar will be in her life no matter what. Despite their tight “friendship”, the two getting back together does not seem to be in the cards.
6 Katy Perry
Katy’s first high-profile relationship was with Gym Class Heroes’ frontman Travie McCoy from 2007-2009 when he was actually more famous than her. She played Travie’s love interest in the music video for "Cupid’s Chokehold" — which is ironically about serial dating.
After their break up Katy fell in love with and married comedian Russell Brand, the two seemed adorable together until they split just one year into the marriage. In 2012 Katy moved onto John Mayer. They two even collaborated together on the song “Who You Love”. However the relationship ended in 2014 and then it was onto the next one (for both of them of course). DJ Diplo was next on Katy’s list and they lasted for about a year. Now, Katy has seemed to have settled (for the moment) with heartthrob Orlando Bloom — let’s see how long this one lasts!
5 Kim Kardashian
No doubt that Kim K made our list. After all, it was one of these relationships that made her famous in the first place, remember? If you keep up with the Kardashians at all, you’ll know that Kim is a hopeless romantic and has always been on the quest for love. Before she made it big, she was married at 19 to Damon Thomas, a music producer who was 10 years her senior. Following that divorce, she dated singer Ray J for three years with whom she made the infamous sex tape that skyrocketed her career. When their relationship went south, Kim was on the hunt for some more arm candy and perhaps someone who could keep her in the spotlight. Kim casually dated stars like Nick Lachey, The Game, Benji Madden, Evan Ross and Nick Cannon. She had a long-term relationship with Reggie Bush and following their split was linked to stars like 50 Cent, Cristiano Ronaldo and Miles Austin.
In 2011 Kim finally decided she was ready for her fairytale wedding and married basketball player Kris Humphries. However, after 72 days of being husband and wife Kim decided she had jumped into things too fast and filed for divorce. Luckily for Kim, the man of her dreams had been right under her nose the whole time. She had been good friends with Kanye West for years but apparently she’d never give him the time of day. In 2012 the two decided to give dating a shot. Fast forward four years, the two are now happily married with two children.
4 John Mayer
John Mayer is known to Hollywood for his soulful music, but also for being smoulderingly sexy and a total heartbreaker. Names in his little black book include Jennifer Love Hewitt, Jessica Simpson, Minka Kelly and Jennifer Aniston. In 2009 when John was 31 he had a quick one-month relationship with a 19-year-old Taylor Swift. The fling ended in Taylor writing that famous break-up song “Dear John”. In the lyrics, Taylor calls out John for messing with her at such a young age and playing “dark twisted games.” I wonder how many of John’s exes were praising “amen” to that one!
Following Taylor, John stayed off the dating radar and then in 2012 dated Katy Perry on and off for about a year. The two songbirds almost seemed like they were ready to tie the knot until breaking it off for good in 2014. I guess getting too serious just wasn't in the cards for the two serial daters.
3 Collin Ferrel
Collin Farrell has a ton of famous names on his dating roster — some unproved rumours, but a lot factual. Colin’s famous flings include Michelle Rodriguez, Angelina Jolie, Britney Spears, Carmen Electra and Lake Bell. Some rumoured flings are said to be with Ashley Scott, Demi Moore, Lindsay Lohan and Rihanna.
On The Ellen Degeneres Show in 2013 Colin divulged one of his most surprising affairs of all — a two year relationship with Elizabeth Taylor. At the time Colin was 32 and Elizabeth was 76. Towards the end of her life, Colin revealed he and Elizabeth became very close in what he considers a romantic relationship although it was never consummated. The irony? Elizabeth Taylor was probably the queen of serial daters concluding her life with seven ex husbands. Colin said he wished he could have been the eighth husband however the two ran out of time.
2 Leonardo DiCaprio
Leonardo DiCaprio is another Hollywood stud with a bunch of rumoured flings. But when you think about how handsome, talented and smooth this guy is, chances are the rumours are probably true. Although he has had relationships with actresses like Claire Danes, Demi Moore and Blake Livley, Leo’s true romantic calling seems to be with supermodels.
Whether it was one date, or a six-year relationship, Leo knows how to pull them in. His long-list of model hotties include Naomi Campbell, Gisele Bündchen, Bar Refaeli, Miranda Kerr, Erin Heatherton, Toni Garrn, Kelly Rohrbach and currently Roxy Horner. Will he ever settle down? Who knows, but when you can have multiple supermodels at your disposal why would you want to?
1 Taylor Swift
Last but certainly not least, Taylor Swift. If Elizabeth Taylor is the serial dating Queen, then we’ll call Taylor the princess. Not only does Taylor thrive off love and relationships, so does her music career. Taylor has made a killing selling albums recounting her multiple failed relationships.
Some men in Taylor’s life inspiring her super successful break-up songs include Joe Jonas, John Mayer, Taylor Lautner, Jake Gyllenhaal and Harry Styles. She has also been rumoured to have dated Eddie Redmayne, Patrick Schwarzenegger, Matthew Gray Gubler and Alexander Skarsgård. In more recent years Taylor has seemed to move away from the heartbreakers dating nice guys like Connor Kennedy and Calvin Harris.
Taylor’s most recent boyfriend is actor Tom Hiddleston. The two have been dating for a month and already seem head over heels for each other. However, fans are counting down the days until a breakup ensues and a record gets released — sorry Taylor but we know you too well!
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