John Cusak, 53

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John Cusak is perhaps best known for his performances in Con Air and Hot Tub Time Machine (among an abundance of other gems). Yet, throughout his thriving career he has never decided to get married. 

Among the numerous stars he has dated, Neve Campbell, Minnie Driver, and Lili Taylor are among the best known. But still, for whatever reason, the bachelor has decided to keep himself unbequethed. 

Oprah Winfrey, 66

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Oprah Winfrey has one of the most inspiring backgrounds on the planet. And because of this, it’s no wonder that she grew to be the megastar that she became. I mean, she even has her own magazine. 

Anyways, like the others on this list Oprah has never married. And for her, the reasons are simple: Why do it? While she has been dating her partner, Stedman Graham, for 25 years, they have never tied the knot. 

Hugh Grant, 59

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Hugh Grant has had a very successful acting career. Some of the more popular movies he’s starred in include Love Actually and Notting Hill. He’s become something of a common face in the so-called rom-com.

Throughout much of this career, the man has been dating nonother than Elizabeth Hurley, another actor who has had her own very successful career. Still, however, after dating for 13 years they called it quits.

 

Winona Ryder, 48

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Winona Ryder is one of the most successful actresses on the planet. Not only has she starred in blockbuster films like Girl, Interrupted and Edward Scissorhands, but she’s also starred in some extremely popular TV shows — namely, Stranger Things

And, perhaps to everybody’s surprise, the actor has never been married. She has, however, dated people like Matt Damon and Soul Asylum’s frontman, Dave Pirnir. She was even engaged to Johnny Depp. But never married…

Al Picino, 76

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Say hello to my little friend? This friend apparently wasn’t a little diamond ring. The famous actor, having won his way into our hearts as the notorious gangster Michael Corleone, quickly took Hollywood by storm. 

While the actor has dated many others in the movie industry, he has surprisingly never married. He has, however, had children — two of them with Beverly D’Angelo and another with Jan Tarrent. 

Ricky Gervais, 58

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Ricky Gervais has had an interesting career. Perhaps gaining his initial ascendency with the original showing of The Office (and then later by producing the remake), the man has had a successful career. 

Meanwhile, Gervais has never married. While some might say this is due to his teeth (just kidding), he says himself that he has no desire. He has been with his current girlfriend, Jane Fallon, for over 30 years. 

Diane Keaton, 74

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Diane Keaton is one of those female actors that set the trend for style and elegance. She’s starred in movies like Annie Hall and Something’s Gotta Give. This thriving career has painted her as a premier actor. 

Despite having played a leading actress in so many romantic comedies, the actress has never married. While she’s dated the likes of Woody Allen and Al Pacino, she’s never found anyone with whom she’d like to tie the knot. 

Jon Hamm, 48

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Jon Hamm is one of those actors that you wouldn’t really expect to get married. Having been in the movies as a typical “stud” character, you’d expect him to live as a sort of bachelor in real life. And so he has. 

Over the course of his career, the man has dated plenty of people. To Jennifer Westfeld, however, he was shackled up with for 18 years. While the two didn’t tie the knot, they did remain together for a long time. 

Tim Robbins, 58

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Tim Robbins has been in an abundance of movies. Among these have been timeless hits like Mystic River and Shawshank Redemption. But would these hits lead him to an everlasting marriage? You can likely guess the answer to that question. 

While Robbins hasn’t gotten married per se, he has definitely done some dating. With his current partner, Susan Surandon, he has been dating her a total of 20 years. Still, he doesn’t want to do the whole marriage thing. 

Bill Maher, 64

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Bill Maher, while not a movie star, is a TV and HBO personality that many of us know. And, whether you like him or loathe him, you still might be curious about those he seems to date. 

While Maher has dated many people — among them include Cara Santa Maria, Karrine Steffans, and Coco Johnson — the man has never wed any of them. It seems as if marriage is far from his mind. 

Matt Dillion, 56

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Matt Dillion is another of those characters who has played a bad boy on the big screen. Starring in movies like There’s Something About Mary and Drugstore Cowboy have solidified this.

The actor, however, has never married. Despite having made his way through a whole suite of relationships — including one with Cameron Diaz — where you think such a proposal might emerge, the possibility never showed. 

Owen Wilson, 51

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Owen Wilson isn’t exactly somebody we’d characterize as a playboy. He might not categorize himself that way either. Wilson, having starred in movies like The Royal Tenenbaums and Wedding Crashers, you think might have tied the knot. 

Nope. He’s dated the likes Sheryl Crow and Kate Hudson, to whom he was engaged. He also had a son with his ex-girlfriends Jade Duell and Caroline Lindqvist. But to none of these women has he ever married. 

Marisa Tomei, 55

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Marisa Tomei was an actor most of us know from her thriving career in the ‘90s and early 2000s. She starred in My Cousin Vinny, Anger Management, and What Women Want. But through it all, she never married. 

Tomei did, however, date a number of notable people, including Lenny Kravitz and Robert Downey Jr. She was even engaged to Logan Marshall-Green. But, again, with none of these people did she ever get married. 

Matthew Perry, 50

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Most of us know Matthew Perry from his role in Friends, playing Chandler. But he has also gone on to star in a handful of movies. He’s acted in The Whole Nine Yards, for instance, as well as Fools Rush In. 

But through it all, he never married. He dated his costar for Fools Rush In, Julia Roberts, and Lauren Graham and Lizzy Caplan. But the question of marriage had never emerge. Maybe one day…

Joan Jett, 61

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Joan Jett, a founding member of the band The Runaways, is one of those rockstars who helped to define a genre. While not an actor per se, she is somebody who’s dating life you might be curious about. 

Well, we can tell you one thing: she never married. While having been rumored to date the likes of Carmen Electra and Chuck Zito, a celebrity bodyguard, she never really came out into a public dating life. 

Alan Rickman, 69

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Alan Rickman we all likely know from his leading antagonist role in Die Hard or as Snape in the ever-popular movie series Harry Potter. But wherever you know him from, you should also know that he never married. 

But despite never being married, this doesn’t mean the man hasn’t maintained long-term relationships. He has been dating his partner Rima Thourton, for example, since they were 18. That’s practically a marriage without the ring. 

Jeremy Piven, 54

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Jeremy Piven (on the right) is an interesting character. He’s starred in Entourage, Serendipity, and the very popular TV show Will and Grace. But throughout all of this, he has never shackled up. 

Unlike many of the other celebrities on this list, Piven is a bit more exclusive. This might be because he likes to maintain his privacy. I mean, who wouldn’t? Anyways, this is one of the many actors who has never married. 

Benicio Del Toro, 53

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Benicio Del Toro is well-known in the acting community and beyond. Having starred in the likes of Traffic and Sacario, this makes sense. And while the man has had an enduring relationship, the two have never married. 

Currently, Del Toro is dating the likes of Rod Stewart’s daughter, Kimberly Stewert. The two have a daughter. Yet still, tying the knot with marriage does not seem to be in the cards. But hey, that’s a personal decision. 

Seth MacFarlane, 46

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Seth MacFalane is likely known to most of us through his extraordinarily popular TV shows, including Family Guy and American Dad. But other than these, he has written and starred in a few movies as well, including Ted and A Million Ways to Die in the West

But, throughout it all, the man has never been married. While this doesn’t mean he hasn’t dated his fair share — most famously having dated Emilia Clarke from Game of Thrones — the man has never tied the knot. 

Adrian Brody, 46

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Adrian Brody has been in many high-profile movies. Some of these include films like The Pianist, and others the likes of Predators. But other than this, he has been a favorite of Wes Anderson. 

Anyways, the man has never married. He’s dated Tori Amos, Keira Knightely, and January Jones, but never married any of them. Perhaps the man just likes to live his life as a bachelor. It’s difficult to say. 

Leonardo Dicaprio, 45

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Leonardo DiCaprio is perhaps one of the most famous bachelors on this list (and, in fact, famous for how much of a bachelor he is). He is often pictured partying on his yacht with many, many women. 

Anyways, the ones he has officially dated are the likes of Bridget Hall, Brittany Daniel, Naomi Campbell, Kristen Zang, Helena Christensen, and Natasha Henstridge. But, of course, he has never married any of them. 

Charlize Theron, 44

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Charilze Theron is one of the top actresses out there. She’s been in movies such as Monster, the remake of Mad Max, and starred as the lead villain in the movie Snow White and The Huntsman

Throughout her career, she has dated the likes of Craig Bierko, Stephen Jenkins, Stuart Townsend, and Keanu Reeves. She’s even dated Sean Penn. But to none of these actors was she ever married. 

Eva Mendes, 46

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Eva Mendes is a star many of us know from the movies Hitch, The Other Guys, and The Place Beyond the Pines. She’s been in so many movies you’d be hard pressed not to recognize her. 

But has this recognition driven her to get married? Of course not. The actress instead has continued her long-term partnership with her costar in The Place Beyond the Pines, Ryan Gosling. The two have two children together. 

Drew Carey, 61

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Drew Carey has created quite the persona for himself. Having starred, written, and produced his own show, this makes sense. Not only does he have the Drew Carey Show, but he starred and hosted the popular Who’s Line Is It Anyways?

But through all this, Carey has never married. While he dated Nicole Jarazc for 12 years, the two never tied the knot. In fact, they split in 2012. It could have been because people kept asking them if they were going to get married. Who knows? 

Lauren Graham, 53

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Lauren Graham is perhaps best known for her performance in Gilmore Girls. While she has been in a handful of movies, including Bad Santa and Sweet November, her most flourishing roles have been in Gilmore Girls

Still, however, throughout this long acting career she has never married. Of the people she has dated, however, are the likes of Peter Krause, Tate Donovan, Matthew Perry, and Marc Blucas. 

Sarah Silverman, 49

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Sarah Silverman is an extremely popular comic. But beyond her comedy she has earned herself a role in a handful of movies and TV shows, including Wreck-It Ralph and School of Rock

But the comedian has never married. Rather, she’s dated the likes of Jimmy Kimmel and Michael Sheen, but never felt the need to tie the knot. Maybe she just wouldn’t find it funny.

Chris Evans, 38

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Chris Evans has had an interesting career, jumping from minor protagonist in the teen-type movie, he moved from tiny star to mega star. Now he helps lead superhero movies like The Avengers

Anyways, despite his rise to stardom, the actor has never gotten married. While he’s dated actors like Jenny Slate, Jessica Bell, and Minka Kelly, he’s gotten married to precisely zero of them. 

Sheryl Crow, 58

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Sheryl Crow has performed some of the most pop songs we can think of. Just to name a few of these, she’s performed the songs “If It Makes You Happy” and “The First Cut Is the Deepest.”

But throughout all of her music career, the performer has never gotten married. A few of the notable people she’s dated were Owen Wilson, Eric Clapton, and even Lance Armstrong. But with none of them was she willing to tie the knot. 

Tyra Banks, 46

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Tyra Banks, much like Oprah, has erected her own dynasty of TV shows and magazines to surround her. She’s had the Tyra Show, for instance, and the increasingly popular America’s Next Top Model

Through all of this, the men she’s dated range from John Singleton, Seal, Chris Weber, and now Erik Asia. While her relationships have varied in length, none have unfolded into marriage.. 

Simon Cowell, 60

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Simon Cowell, the TV persona to the show America’s Got Talent, often offers harsh criticism to those he watches perform. He is, in fact, what many consider to be the most notorious critic there is. 

While extremely critical on the show, his personality is not so bitter off air. Yet still, he has never married. Instead, he has been with Lauren Silverman, his long-term partner. The two have a son together.