15 Hollywood Stars Who Have More Than One Girlfriend

Stargazing used to mean staring up at the sky during the night. But these days, there are lots of people that would first think of watching the famous among us when hearing that term. It makes some sense, as celebrities seem to have lives that are all glitz and glamour considering that many of them are rolling in money and have access to things we’ll never know. In some cases, that can mean that they are able to be intimately involved with more than one woman at a time. While we do think that they are missing out on the joys of a monogamous relationship unless all involved are able to know and trust one another, there is no doubt that people are tantalized by this idea. Realizing that is what inspired us to put together this list of fifteen stars who have more than one girlfriend.

In order for a celebrity to be up for consideration for possible inclusion on this list, he/she first and foremost has to be a celebrity. For our purposes, it doesn’t matter what he/she did to earn his/her following so you may find actors, musicians, directors, athletes, or others here as long as they have a substantial following. Next, we want to make it clear that these people don’t need to be involved with multiple people now as long as they have in the past. There needs to be something that points to them being involved with someone while also having another woman/man in their life at some point. For our purposes, that can be cheating as the relationships seem to have some meaning. Otherwise, these are people that are in open relationships of some kind.

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15 Tilda Swinton

Via newyorker.com

A little bit of a cheat as you may not have expected us to include a woman, plus she is involved with both a man and woman instead of only ladies, we still feel that Tilda Swinton fits the spirit of this list. Best known for the Chronicles of Narnia film series, as well as The Beach, Constantine, We Need to Talk About Kevin, and Snowpiercer, she is immensely talented, to say the least. Somebody who seems like she was born to be an artist, first and foremost, when we think of her, authenticity comes to mind. Reportedly linked to with a female live-in lover while also still attached to a male paramour, it seems as though they all make for quite the threesome.

14 Ashton Kutcher

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An actor that started out his time in the spotlight as part of the sitcom That ‘70s Show, Ashton Kutcher found further TV success as part of the show Two and a Half Men as well. Also a movie star, he is notable for his work in films like The Butterfly Effect, What Happens in Vegas, Valentine's Day, and No Strings Attached among many others. Also somebody who has gotten a lot of attention for his work outside of films and television, he has found a lot of success as an entrepreneur on top of being a part of some high-profile relationships. Previously married to Hollywood superstar Demi Moore, he would end up divorced after reports surfaced that he had stepped out on her, which is why he belongs on this list.

13 Jude Law

Via mashable.com

Somebody who comes off like quite the charmer, Jude Law has proven time and time again during his acting career that he can play characters that come off in a wide range of ways. Best known for his work in movies like The Talented Mr. Ripley, Road to Perdition, Cold Mountain, Closer, and The Holiday, it seems as though he has had his fingers in pretty much every genre. Also a mainstay of tabloids throughout much of his career, his relationship with the gorgeous Sienna Miller seemed like it was destined to be for a long time. Then it came to light that he had been sleeping with his children’s nanny, something he apologized publicly for, which seems like something a lot more serious than a fling to us.

12 Gerard Butler

Via hollywoodreporter.com

Somebody who seemed to become a huge star overnight, when Gerard Butler’s work as King Leonidas in 300 was released to the masses, it was a star-making role since he exhibited so much charisma. Able to take advantage of that momentum for a while, he went on to lead other movies like RocknRolla, The Ugly Truth, Gamer, Olympus Has Fallen, and the underrated movie Law Abiding Citizen. Unfortunately, he has had more misses than hits over the last several years, but he still lands major roles consistently and is famous around the world. Involved with someone for a quite a while, he earned his spot on this list because he broke up with her in 2016 partly because so many women were interested in him, and he wanted to spread his affections around.

11 Ethan Hawke

Via Imgur.com

Without a doubt one of the fastest rising stars during the nineties, there was a time when it seemed as though Ethan Hawke was on his way to being as famous as people like Tom Cruise or Tom Hanks. Best known for movies like Alive, Reality Bites, Gattaca, Training Day, and Boyhood, he has been in a good mix of blockbusters and smaller films too. However, arguably his greatest achievement in the film industry is starring in and working on the screenplay for the Before trilogy, which are three of the most compelling relationship movies ever made. That is kind of funny, though, as his marriage to Uma Thurman ended in horrible fashion when he was caught sleeping with his nanny. Going on to marry her after that, it is clear that she held a big spot in his heart.

10 T-Pain

Via hypebeast.com

A rapper that has been a part of a long list of songs that got people off their chairs and on the dance floor, T-Pain has been around for far longer than many expected already at this point. Noted for his use of auto tune, an effect that many music connoisseurs have disdain for, there is no doubt that he uses it to great effect and has a great ear for creating catchy music. Best known for his contributions to songs like “Low,” “Buy U A Drank (Shawty Snappin’),” “Kiss Kiss,” and “Blame It” among many more, there is something about him that makes it feel like fun times are coming. Married to the same gorgeous woman since 2003, he has spoken publicly about their agreement that allows for other women to be brought into their relationship.

9 Leonardo DiCaprio

Via independent.co.uk

One of the biggest stars in the world ever since he starred in the movie Titanic, it isn’t a coincidence that Leonardo DiCaprio was a part of a movie that was the most successful of all time for several years. Not only a part of a flick that goes far beyond deserving to be called a blockbuster, in the years since then, he has gone on to star in a series of films that have been acclaimed by critics and audiences alike. Best known for other films like Gangs of New York, Catch Me If You Can, The Aviator, The Departed, Inception, and The Wolf of Wall Street, his work will last the test of time. Someone who gets a lot of attention for the fact that he seems to be with a different model all of the time, there have been times that he has schmoozed two girls during different dates on the same day.

8 Mario Lopez

Via thefamouspeople.com

One of the stars of a show that is remembered by legions of people as a fantastic part of their youth, Mario Lopez was a key part of the success of the series Saved by the Bell. Continuing to play A.C. Slater after that show came to an end, he played one of the main characters in the spin-off Saved by the Bell: The College Years as well. These days making his living as a television host, he has been a part of Extra, America's Best Dance Crew, The X Factor, and MTV's Top Pop Group, on top of guesting on a number of other shows. Seen as pretty squeaky clean throughout much of his career, his image took a major hit when he married Ali Landry only to have her annul their marriage two weeks later since he’d already cheated on her.

7 Scott Disick

Via zimbio.com

An amazing part of pop culture for a number of years now, the fact that Scott Disick has been and continues to be famous blows our mind. Becoming a known entity because he was involved with Kourtney Kardashian for many years, he became a star by dating a woman that was a celebrity for dubious reasons herself. Made all the worse because his brand had a lot to do with coming off as a jerk, he appeared in a series of “reality” shows alongside the Kardashian-Jenner clan for several years. Single now because he was caught with other ladies again and again during his relationship, he has stepped things up a great deal more now as he is photographed with throngs of women sometimes.

6 Russell Brand

Via hellomagazine.com

An actor, comedian, TV presenter, writer, and all-around personality, on top of all of that, Russell Brand has spent time as both a radio and podcast host in the past. Somebody whose energy level is incredibly off-the-charts, his manic levels of intensity make it seem like he has to keep going night and day which is probably why he has struggled with things like drugs. Previously married to one of the biggest singing stars in the world today, Katy Perry, that relationship went down in flames in a very public way. Seemingly somebody who has also gone nuts in his intimate life for several years, he has spoken about his love for threesomes and has also been photographed on dates with several women at a time.

5 David Letterman

Via dailymail.co.uk

Without a doubt one of the most beloved talk show hosts in the history of the business, if you ask us, the only person that has beaten him out in that industry is the legendary Johnny Carson. Debuting on late night TV all the way back in 1982, David Letterman continued to be a staple of that all the way up until his retirement on May 20th, 2015. However, he wasn’t as through with hosting as the world initially thought as he has since signed on to host a series of hour-long programs for Netflix that will be available to their customers in 2018. Historically someone who has kept his personal life out of the spotlight, aside from anecdotes on his shows, he was the focus of a great deal of controversy for a time when a lasting affair of his came to light. Tackling it head on, he came clean during a memorable episode of his show and in doing so put an end to the stories that had dogged him.

4 Ben Affleck

Via tvguide.com

An actor with four distinct eras of his career, Ben Affleck started out as an actor on the rise before becoming a star with movies like Good Will Hunting and Armageddon. Then, pretty much everywhere, he was a constant tabloid presence during his relationship with Jennifer Lopez, and he had several films bomb before he disappeared from the spotlight for a while. Able to have a come back because of his impressive directing career, his films Gone Baby Gone, The Town, and Argo earned him Hollywood’s respect again. Now a huge movie star that gets attention for playing Batman, as well as starring in Gone Girl, his career is at an all-time high. However, his name is also being mired in controversy again as it came to light that he is now involved with a Saturday Night Live producer he had a long-running affair with while still married to Jennifer Garner.

3 Floyd Mayweather, Jr.

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One of the best boxers of all time, Floyd Mayweather, Jr. deserves to be in the same conversation as people like Mike Tyson, Muhammad Ali, Sugar Ray Robinson, and Evander Holyfield. Currently possessing a perfect record of fifty wins and zero losses, he has beaten some legendary fighters and recently garnered headlines for his bout against Conor McGregor. A member of several boxing Hall of Fames and an immensely wealthy person, he isn’t just good at the part that happens in the ring but his boastful ways make him a promotional machine. Recently speaking about his personal life during a very unorthodox interview, in September of 2017, he claimed to have seven girlfriends which made him a total shoo-in for inclusion on this list.

2 Charlie Sheen

Via torontosun.com

A star since the mid to late eighties, Charlie Sheen is a part of a family that is an acting dynasty including his father, Martin Sheen, and brother, Emilio Estevez. The star of movies like Platoon, Wall Street, Young Guns, as well as the Major League and Hot Shots series of films, that alone makes for an impressive resume. However, he also spent years as the star of a show that was a massive rating hit with audiences, Two and a Half Men. Impressive career aside, he also has a well-publicized history of public controversies in his personal life including being a customer of former “Hollywood Madam” Heidi Fleiss. That said, it was during his public meltdown involving tiger blood and winning that he earned his way on this list because he had a relationship with three women at the same time, his so-called goddesses.

1 Arnold Schwarzenegger

Via mensjournal.com

Unquestionably one of the biggest action stars to ever live, Arnold Schwarzenegger has anchored so many beloved films that it is simply incredible. Starting out his time in the spotlight as a bodybuilder, he was so jacked that he won the Mr. Olympia contest seven times which is what led to him getting a chance to act in the first place. Also able to become a successful politician, he served as the Governor of California from 2003 until 2011 which is proof positive that he seems to be able to kill it no matter what he tries to do. Also quite the ladies’ man in his time, prior to getting married, he spoke often about sleeping with many women. But then, the world thought things calmed down during his marriage. However, years later, it came to light that he and his housekeeper’s relationship was more than it seemed to be as she gave birth to his son, a revelation that led to his divorce.

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