Many celebrities date around. I mean, if you can, why not? You can’t really blame them. They are good looking, talented, and famous. They are instantly recognizable on the street, in a restaurant, or at the club. Men and women from all over the world want to be with them. Some celebrities like to keep their personal lives private. Others, though they may try, really don’t try too hard. Because they live their lives in the public eye, we are privy to their friendly encounters, dates, and hook-ups. If a celebrity is a serial dater, it becomes pretty apparent pretty quickly.
Hollywood is pretty forgiving when it comes to the romantic history of its celebrities. I mean, look at how many stars are only stars because their private tapes came to light! Though it has been going on for generations, it is now pretty much acceptable to be publicly open about your romantic liaisons without damaging your celebrity status. There are some who take this to a whole other level. I’m talking about the likes of Wilt Chamberlain, Gene Simmons, and Charlie Sheen, who claim romantic conquests that number in the thousands. No, we’re not going to cover the groupie escapades that they boast on. Instead, this is a list of 15 celebrities who genuinely have dated just about everyone. If you take notice, you might even see how many overlap. What’s that called… being Eskimo brothers? In that case, half of Hollywood is related.
15. Pamela Anderson
Before Kim Kardashian, and before Paris Hilton, there was Pam Anderson. She was a bonafide Baywatch babe who was the object of every young man’s desire. She wasn’t the first celebrity to have her bedroom antics broadcasted to the four corners of the world but she was the first of the Information Age. It shed a light on her personal life like never before and her love life became an open book. Many celebrities before her were known as “serial daters,” but she brought it to a new level. She’s been romantically linked to Scott Baio, Dean Cain, Bret Michaels, Antonio Sabato Jr., Vince Neil, David Charvet, Kelly Slater, Marcus Schenkenberg, Michael Bolton, Fred Durst, Stephen Dorff, and then there’s her marriages to Tommy Lee, Rick Salomon (twice), and Kid Rock. That’s not even mentioning the rumored trysts with Criss Angel, David Spade, Slash, and Sylvester Stallone!
The lady’s man Drake has been beloved since his young television days, and why not? He’s talented, charming, and being a huge music star doesn’t hurt either. He’s been romantically linked on-and-off with tennis superstar Serena Wiliams for years. Then there’s his history with Rihanna, not to mention Tyra Banks, Zoë Kravitz, and reality television star Cat Washington. He once made it known he had something of a crush on the beautiful Kat Dennings, and BAM! She went out with him. He said, “I just always had a huge crush… and she was kind enough one night to oblige me and we went out for dinner.” I never knew that worked (Kat, if you’re reading this, I also have a huge crush – contact me?). Some girls even became famous because Drake took a liking to them. Take the case of Bernice Burgos, the former Bronx waitress who became famous after being photographed smooching with Drake in Australia. Now she’s a popular Instagram model!
13. Lindsay Lohan
Back in January 2013, a list was recovered and published in the tabloids reportedly written by Lindsay Lohan. This list, written when she was gossiping with a group of friends, contained the names of 36 celebrities with whom she had, ahem… relations. Afterwards, she tossed the list, which was found and published. All the single names were shown in full view but the magazine blurred out names of celebrities who were married or otherwise romantically involved. That list included hockey player Aaron Voros, Ashton Kutcher, Adam Levine, Garrett Hedlund, Guy Berryman (from Coldplay), Zac Efron, Evan Peters, Lukas Haas, Justin Timberlake, Wilmer Valderrama, Colin Farrell, James Franco, Benicio del Toro, Jamie Dornan, Joaquin Phoenix, Stavros Niarchos III, Heath Ledger, Ryan Phillippe, footballer Danny Cipriani, Max George, and Orlando Bloom. Conspicuously absent from the list were her known former relationships with Aaron Carter, Shaun White, Jason Segel, Harry Judd, and Samantha Ronson. Even director Brett Ratner admitted he hooked up with her once.
12. Ryan Gosling
He’s young, good looking, successful. Women around the world fell in love with him after he appeared in the romance film, The Notebook. After that his stock with the opposite sex grew with films like Crazy, Stupid, Love and La La Land. Why wouldn’t Ryan Gosling date as many beautiful women as he could before settling down? Sure, we all know he’s found the one in his beautiful wife Eva Mendes (no settling there!). However, before getting hitched and having two daughters together, Gosling was known for hitting the town, always with a beautiful woman on his arm. He’s been linked to some super famous, super-hot women. He counts among his exes the likes of Sandra Bullock, Kat Dennings, Olivia Wilde, Blake Lively, Famke Janssen, and Rachel McAdams. Not too shabby!
11. Amber Rose
One of the new generation of stars famous for, well, being famous, Amber Rose is another one who has dated a who’s-who of the entertainment industry. After being a video vixen, she caught the eye of Kanye West and the two shared a high-profile romance. She also was married to rapper Wiz Khalifa, and they have a son together. She’s also been romantically linked to rappers Ryan Banks and Offset, dancer Val Chmerkovsky, basketball players Terrence Ross, Amar’e Stoudemire, and James Harden, football players Myles White, Reggie Bush, and Odell Beckham Jr., and comedic actor Eric André. She’s rumored to have hooked up with Nick Simmons (Gene’s son), Lebron James, Chris Brown, French Montana, and rapper Joe Budden. In 2015, she spoke out publicly against women being shamed for their sexuality and led the Los Angeles Sl*tWalk in honor of all those who have been judged and demeaned. Amber is currently dating rapper 21 Savage. Could she be settling down?
10. Paris Hilton
She’s dated athletes, musicians, and actors. She’s currently seeing Leftovers actor Chris Zylka. The mega-rich heiress has been engaged twice (model Jason Shaw in 2002, and Green shipping heir Paris Latsis in 2005), but never married. Besides that she’s dated, or been caught canoodling with, the likes of Thomas Gross, Josh Upshaw, River Viiperi, director Todd Phillips, DJ Afrojack, Cy Waits, footballer Cristiano Ronaldo, Doug Reinhardt, Benji Madden, Jared Leto, 50 Cent, Brody Jenner, DJ AM (Adam Goldstein), Adrian Grenier, Tyler Atkins, Kid Rock, Andy Roddick, Travis Barker, Jamie Kennedy, producer Scott Storch, Stavros Niarchos III, Val Kilmer, Simon Rex, Chad Muska, Jake Sumner, Fred Durst, Nick Carter, musician Deryck Whibley, Mark McGrath, director Vincent Gallo, Girls Gone Wild creator Joe Francis, Rick Salomon, Edward Furlong, and Randy Spelling. That’s not even mentioning all the guys she’s been rumored to have hooked up with. She’s definitely in the serial dater hall of fame!
9. Justin Timberlake
Justin Timberlake is a quadruple-threat: he can act, he’s funny, he can dance, and he sure can sing. Oh, and he can seal the deal with some hot women! In his single dude days, JT was known to be in the company of some of the most beautiful women in Hollywood, and that was even before he went solo and brought “Sexy Back.” In 2012, all the single ladies in Hollywood collectively cried in disbelief when he married Jessica Biel. As a teen, he dated Stacy Ferguson, who would later go on to become musically known as Fergie. His first high-profile relationship was with his first love, Britney Spears. But after she reportedly broke his heart, he dated his backup dancer Jenna Dewan, now Dewan-Tatum (as in, wife of Channing Tatum). He then became linked to a veritable who’s-who of the entertainment industry, including Olivia Wilde, Olivia Munn, Lindsay Lohan, Rihanna, Scarlett Johansson, Cameron Diaz, Alicia Keys, and Mila Kunis.
8. Kaley Cuoco
Kaley Cuoco is the sweetheart from TV’s The Big Bang Theory, and like everyone else, in real life, she’s looking for love. After dating Thad Luckinbill, Jaron Lowenstein, and Josh Henderson in the early 2000s, Cuoco hooked up with her Big Bang co-star, Johnny Galecki. The pair dated secretly from 2008 to 2010. Unlike their television relationship, their real-life coupling didn’t work-out. She was then linked to Christopher French, Josh Resnik, and musician Bret Bollinger, before she had a brief fling with Superman himself, Henry Cavill. After about a month, in 2013, that ended and she started seeing former professional tennis player Ryan Sweeting. They quickly got engaged, and then married, changing her professional name to Cuoco-Sweeting. By the end of 2015, she was back to Cuoco, and their divorce was finalized in 2016. Since then she’s been seeing equestrian Karl Cook.
7. Leo DiCaprio
Leo DiCaprio is a Toyota Prius-driving, activist-inspiring, acting legend in his own time. You would think would be more public about his incredible serial dating habits. He’s too much of a low-key guy, I suppose. He’s been a super heartthrob since the 1990s and women just can’t help falling for him. Though he can’t seem to catch a break at the Academy Awards, he has no problem winning over the hot ladies with films like Romeo + Juliet, Titanic, and Wolf of Wall Street. He’s been linked with Bijou Phillips, Gisele Bündchen, Bar Rafaeli, Nina Agdal, Blake Lively, Naomi Campbell, Margarita Gauchet, Natalie Denning, Eva Herzigová, Bridget Hall, Kristen Zang, Erin Heatherton, Madalina Ghenea, Toni Garrn, and the beautiful Rihanna! Wow! There sure are a lot of supermodel names in that list.
6. Taylor Swift
Here she is, the one you know was going to be somewhere on this list: Taylor Swift. She’s young and young people date; there’s no problem with that. However, when you’re an international star, your dating exploits become tabloid fodder. She is perpetually looking for “Mr. Right,” and I’m sure she’s enjoying the search. The talented singer tends to channel her heartache into her music and it’s made for some of her biggest hits. She’s been linked to John Mayer, Tom Hiddleston, Lucas Till, Taylor Lautner, Zac Efron, Chord Overstreet, Conor Kennedy, Calvin Harris, Eddie Redmayne, Jake Gyllenhaal, Joe Jonas, and the late Cory Monteith. Plus, there are rumors she hooked up with Patrick Schwarzenegger, Tim Tebow, and Garrett Hedlund. Here’s hoping you finally find what you are looking for, Taylor!
5. Ryan Reynolds
When you’re as good looking as Reynolds, I guess you can forgive the fact that fellow Canadian, also named Ryan, once dated your wife, Blake Lively. After all, Ryan Reynolds is no slouch in the “serial dating” arena himself. He’s a great looking guy, funny, and a pretty good actor. In the 1990s, he was dating the beautiful Traylor Howard, co-star on the popular television show Monk. Then he was linked to Kristen Johnston and the adorable Rachael Leigh Cook. In 2002, he married Alanis Morissette, but that ended in 2007. He then found comfort in the arms of the sizzling Scarlett Johansson, whom he married in 2008. Unfortunately, their marriage ended in 2011. He dated Charlize Theron and Sandra Bullock for a time, before finding his true love, Blake Lively. The pair married in 2012. Interesting note: Melissa Joan Hart, star of the 1990s sitcom Sabrina the Teenage Witch, admitted she made out with Reynolds when was 19.
4. James Franco
Though not as publicized as some of the others on this list, James Franco has had quite a few girlfriends in the public eye, not to mention the tons of rumored flings. Who knows if he’ll ever settle down but for now he seems to be enjoying the dating scene. He appears to be single right now, but that could just mean he’s seeing someone outside of the Hollywood mainstay. Being famous is not necessarily a prerequisite to dating Franco, as he’s been known to date outside of the entertainment industry. He’s been involved with such stars as Lana Del Rey, Amanda Seyfried, model Erin Johnson, Lindsay Lohan, Sienna Miller, Marla Sokoloff, Ashley Hartman, model Agyness Deyn, and Ahna O’Reilly. The rumor also has it that back in 2013 he was involved with Game of Thrones star Emilia Clarke, with a possible engagement that was in the works. Neither ever confirmed the rumor.
3. Nick Jonas
Former purity ring-sporter, Nick Jonas dived into to the former-Disney Channel star pool and came out a serial dater. He was always a hit with the preteen crowd in his early days with his brothers. Once he got a little older and released his solo album, women went crazy! At that point, he put his Disney (and purity ring) days behind him. His older brother, Joe, was something of a serial dater and Nick took after him. His first love was Miley Cyrus. When that didn’t work out, he began seeing others like Selena Gomez, Jordan Pruitt, Courtney Galiano, Delta Goodrem, Gigi Hadid, and Olivia Culpo. He’s really close to his brother Joe’s ex-girlfriend, Demi Lovato. The pair appeared together on James Corden’s Carpool Karaoke and admitted, though they are very close, there’s never been any romantic shenanigans (nevertheless, she also admitted that she cares deeply for him, leading fans to believe he’s the inspiration for a few songs).
2. Wilmer Valderrama
Wilmer Valderrama claims he’s “been blessed” when it comes to his talent with the ladies. The sitcom star that portrayed Fez on That 70s Show, certainly has done quite well for himself with the ladies. I guess he burst onto the Hollywood dating radar in 1999, when he was seen dating Ariana Richards (you remember, the young girl from Jurassic Park), then he romanced Jennifer Love Hewitt. In 2000, he entered into a 2-year relationship with Mandy Moore. Then in 2004, he hooked up with a young Lindsay Lohan. They were together two months before they got engaged! That lasted another two months before they broke up. Lohan refers to Valderrama as her “first love.” He then dated Demi Lovato for six years, before they too broke up. He was linked in 2012 to Minka Kelly, and again last year after his breakup with Lovato. In between, he’s been seen with Ashlee Simpson, Avril Lavigne, Mischa Barton, and Rihanna. It was even rumored he had a fling with Mila Kunis.
1. John Mayer
We can’t have a discussion about serial daters and not place John Mayer in your ring of honor. Aside from being an incredibly talented musician, he’s known for his never-ending list of women. The man’s a playboy! Is he a notorious womanizer, or just putting himself out there in hopes that one day he finds “the one?” Even though he has no problem kissing and telling, or crooning about his love life, there are still plenty of women in Hollywood that don’t mind taking a crack at him! Can you blame them? C’mon ladies, imagine the crooner serenading you on the couch as he lies in your lap. See what I mean? Some of his more notable girlfriends include Jennifer Love Hewitt, Vanessa Carlton, Minka Kelly, Jessica Simpson, Mandy Moore, Jennifer Aniston, Kim Kardashian, Scheana Marie, Cameron Diaz, Katy Perry, and, of course, Taylor Swift.
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