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Zac Efron: The actor, 25, had a romance with his High School Musical co-star Vanessa Hudgens and also has been linked to Lea Michele, Taylor Swift, and Lilly Collins. And The National Enquirer reported that Efron’s life is falling apart--he had a shocking collapse due to an alleged heroin overdose while partying in his New York City hotel suite.
Simon Cowell: The X Factor mogul, 53, has never been married and has lived a playboy lifestyle for years, with his many girlfriends including TV reporter Terri Seymour, singer Sinitta (who has claimed she aborted Cowell’s baby), makeup artist Mezhgan Hussainy, and actress Carmen Electra. In a shocking scandal this summer, the public learned Cowell had impregnated Lauren Silverman, the wife of his best friend. The Silvermans divorced, and Cowell has hinted he might marry his baby mama. However, as RadarOnline.com recently reported, Cowell and pregnant Silverman were spotted in their SUV arguing heatedly over “trust issues.”
Kanye West: The “Yeezus” singer, 36, is Kim Kardashian’s baby daddy—but he hasn’t married her. During Kardashian’s pregnancy, shocked fans also saw West cuss out photographers in front of her and neglect to open doors for his baby mama.
Al Pacino: Pacino’s The Godfather character had a memorable wedding scene, but in real life, the actor, now 73, has never made it down the aisle! Still, he hasn’t lacked for female company, as his list of past girlfriends includes Diane Keaton, Tuesday Weld, Marthe Keller, Kathleen Quinlan, and Lyndall Hobbes. Pacino had a daughter in 1989 with girlfriend Jan Tarrant and twins with Beverly D’Angelo during a long relationship from 1996-2003, but never put a ring on it.
Justin Bieber: Since Bieber’s on-again, off-again relationship with Selena Gomez finally ended, the pop singer, 19, has been linked to various brunette babes, including model Ashley Moore. Bieber cause a stir earlier this year when he visited the Anne Frank House and suggested she “would have been a belieber” if she were alive today. And while on tour in Germany, the star who’s been plagued by legal issues and reports of wild behavior invited a group of Playboy bunnies onto his concert bus.
Andy Dick: The comedian, 47, has had a turbulent love life, fathering a child with his only wife and then having two more kids with a girlfriend. Dick won new fans with a heartwarming stint on Dancing with the Stars last season but told shocked reporters at the reality show’s finale about his Real Housewives of Beverly Hills star girlfriend, Jennifer Gimenez, “I’ve had my eye on a couple of other people. I want to open up the relationship. I’m going to play the field.” The couple soon split up. As RadarOnline.com has reported, Dick recently was caught on video peeing on a public street and fled rehab after an intervention attempt by friends.
Chris Brown: The singer will never live down his 2009 assault on girlfriend Rihanna. And incredibly, in 2012, Brown, 24, resumed his relationship with Rihanna while also simultaneously dating Karrueche Tran. He allegedly broke up with Tran, then got back together with her after things didn’t work out with Rihanna. And after a judge revoked Brown's probation stemming from the Rihanna assault incident, Brown was seen partying at the Playboy Mansion with an unidentified woman this summer.
Jon Gosselin: After a nasty split from his wife Kate during the filming of their reality show Jon & Kate Plus 8, Jon went on a playboy spree with young girlfriends Hailey Glassman, Morgan Christie and Kate Major. Glassman later claimed Gosselin cheated on her and tipped off the paparazzi who wanted pictures of them. Major told RadarOnline.com that “Jon was always trying to ruin Kate and accuse her of being a bad mother.” Kate recently sued Jon for allegedly hacking her computer and phone to help an author write a tell-all book. The former reality TV dad, 36, is now working as a waiter and admitted he doesn’t pay Kate any child support for their eight kids.
Bill Maher: Comedian Maher, 57, has made his never-married status a punch line! Maher said on his website, "I'm the last of my guy friends to have never gotten married, and their wives — they don't want them playing with me. I'm like the escaped slave — I bring news of freedom." His former girlfriend, Playboy Cyber Girl Coco Johnsen, sued him in 2004, claiming he had promised to marry her; the lawsuit was dismissed. He’s also dated hip hop model Karrine Steffans and science educator Cara Santa Maria.
Jude Law: The English actor got a divorce from his only wife, actress Sadie Frost, in 2003. Two years later, following tabloid reports, Law admitted that he'd cheated on his fiancee Sienna Miller with his children's nanny. Law made a public apology, saying, "I am deeply ashamed and upset that I've hurt Sienna." But the now 40-year-old actor didn’t stop his womanizing ways after an on-again, off-again relationship with Miller. Model Samantha Burke had his love child in 2009 and while Jude first denied being the daddy, a paternity test proved otherwise. In 2012, he dated actress Ruth Wilson, and this year, he was linked to model Alicia Rountree, 25.
Leonardo DiCaprio: The Titanic actor is 38 and has never settled down--instead, he’s been a modelizer! DiCaprio’s model ladies have included Kristen Zang, Emma Mille, Gisele Bundchen, and Bar Refaeli. He also reportedly had a brief relationship with actresss Blake Lively before dating yet another model, Erin Heatherton. But since May 2013, DiCaprio has been photographed with German model Toni Garrn.
Scott Disick: Kourtney Kardashian’s baby daddy is known for avoiding work, making himself a “Lord,” partying with other women, dressing like a dandy, and dissing her postpartum weight after she gave birth to their second child, Penelope. Disick, 30, told Ryan Seacrest in 2013 that he and Kourtney have no plans to wed. “I think if it's not broke, don't fix it. You know what I mean?,” he said, adding, in a not-so-enthusiastic relationship endorsement, “We’re decently happy.”
George Clooney: No one was surprised when Hollywood’s most confirmed bachelor, 52, recently split from his latest girlfriend Stacy Keibler. The Gravity star – who was only married once, to actress Talia Balsam from 1989 to 1993 – said he won’t wed again because his priority is his work and he doesn’t want any children. A long list of women have found that Clooney is a commitmentphobe, including actresses Kelly Preston and Krista Allen, TV personality Lisa Snowdon, waitresses Celine Balitran and Sarah Larson, and model Elisabetta Canalis. In an interview with Esquire, Clooney said of Balitran, his girlfriend from 1996-99, "She lasted as long as I think she was going to last."
Charlie Sheen: “Winning” Sheen is a three-time loser in marriage, after divorcing Donna Peele, Denise Richards, and Brooke Mueller. The 48-year-old now single Anger Management actor has never lost his penchant for porn stars and he spent thousands on Hollywood madam Heidi Fleiss’ prostitutes in the ‘90s. Early in 2013, Sheen Tweeted that Richards -- who is raising her kids with Sheen as well as his and Mueller’s -- is his “favorite ex-wife. She’s smoking hot.” Sheen went ballistic when news of his planned meet-up with Teen Mom turned porn star Farrah Abraham got leaked.
David Arquette: After the actor and wife Courteney Cox announced their split in 2010, Arquette told Howard Stern that he and Cox hadn't had sex in four months. The new bachelor then threw himself into partying and wound up in rehab for alcohol abuse. As RadarOnline.com recently reported, Arquette, 42, took his girlfriend Christina McLarty out to dinner in Los Angeles –but just a few hours later, he was spotted flying solo at the Crazy Girls strip club. Arquette has admitted going back to his old drinking and drug using ways
Bradley Cooper: The Silver Linings Playbook star, 38, had a short marriage to Jennifer Esposito from 2006-07 and has been footloose ever since. Cooper’s girlfriends have included Jennifer Aniston, Renee Zellweger, and Zoe Saldana. Earlier this year, Life & Style reported that in a three-day period, the Hollywood Romeo asked MTV host Laura Whitmore for her phone number, danced with Alice Eve at a BAFTA after party but left the bash with Gemma Arterton, and flirted with Suki Waterhouse at the Elle Style Awards. As of August 2013, it appeared that Waterhouse was his steady girlfriend.
John Mayer: The “Your Body Is A Wonderland” singer, 35, hasn’t hesitated to explore! Worse, he’s a kiss and tell playboy. In 2009, Mayer blabbed outside a New York gym about his breakup with Jennifer Aniston. In another TMI moment, he said ex-girlfriend Jessica Simpson “was like….sexual napalm." The musician has also romanced Jennifer Love Hewitt, Cameron Diaz, Minka Kelly, and Taylor Swift (whose song “Dear John” reportedly concerns his manipulations). In a New York Times interview, Mayer said, "I should be having sex with more girls," and amazingly, famous women continue to date him. His latest gal is Katy Perry.
Ryan Phillippe: The actor who was married to Reese Witherspoon and fathered her two kids allegedly cheated on her with his Stop Loss co-star Abbie Cornish, causing their 2006 divorce. Phillippe and Cornish lived together but broke up in 2010. The star, now 38, fathered another child during a brief relationship with actress Alexis Knapp. Since then, Paulina Slagter, just 21, has been his on-again, off-again girlfriend – but he’s also been spotted with Twilight actress Ashley Greene.
Jack Nicholson: The notorious ladies’ man, now 76, knew he’d be unfaithful when he married—for the only time--to Sandra Knight in 1962. They divorced, and Nicholson’s reported list of conquests included actresses Michelle Phillips, Susan Anspach (with whom he had a love child), Rachel Ward, Julie Delpy, and Laura Flynn Boyle. He also allegedly bedded models Veruschka Von Lehndorff and Winnie Hollman (with whom he had another love child). When Nicholson impregnated Rebecca Broussard, it ended his longterm relationship with Anjelica Huston; he never married Broussard despite two kids. “I’m preoccupied with sex,” the Oscar-winning actor has shrugged.
Brad Womack: The 40-year-old Texas winemaker was The Bachelor twice on ABC TV -- during season 11 in 2007 and season 15 in 2011. The first time, Womack rejected all of the bachelorettes and the second time, he proposed to Emily Maynard but they split up soon after the show’s finale aired. In 2012, Womack said ungallantly of Maynard, “I think I dodged a bullet with that relationship.” He’s still single but it was reported in summer 2013 that he was dating Bachelor season 17 contestant, Ashlee Frazier.
Michael Lohan: Lindsay Lohan’s father has had a troubled history with women. Michael’s wife Dina divorced him in 2007 and in 2012, it was revealed he’d fathered a child while they had still been married. In 2011, Lohan was arrested for harassing his ex-girlfriend Kate Major. But incredibly, they patched things up and Major had his sixth child, son Landon, earlier this year; recovering addict Lohan, who hasn’t married Major, gushed about “new beginnings.”
Wilmer Valderamma: The That ‘70s Show actor, 33, won himself a permanent place in the doucebag hall of fame after telling Howard Stern in 2006 about all his ex-girlfriends! Valderamma rated Jennifer Love Hewitt “an eight” in bed, mused about Lindsay Lohan’s breasts, and claimed he took Mandy Moore’s virginity. Outraged Moore said, “That is utterly tacky, not even true,” while Hewitt denied having sex with him. Valderamma boasted that he was well-endowed: “It’s over eight inches.” He’s now reportedly seeing The X Factor judge Demi Lovato, 21.