Maybe they just aren’t cut out for marriage, and honestly, has being single ever looked better than it does for Leonardo DiCaprio? Or maybe they’re happy in their long-term partnership, no paperwork necessary (here’s looking at you Oprah), but these celebs have chosen to skip the altar entirely, in favor of living life a little less conventionally. And while marriage isn’t necessary to ride off into the sunset with your beloved by your side, some of these celebs may still take the plunge. You never know which of these celebs might pull a George Clooney and say goodbye to the single life when we’re least expecting it.
1. Owen Wilson
No one will be crashing Wedding Crashers actor Owen Wilson’s wedding. Why? Because he won’t be having one. Wilson’s had a few high profile romances in his youth, but he’s happily settled into life as a single dad since then, and we think that’s swell (for now).
We’ll never say never to wedding bells for Wilson, especially considering the actor has confessed that he is growing “more sentimental” as he gets older. Maybe it’s time the actor tried dipping back into the Hollywood dating scene — may we suggest calling his Marley & Me screen-wife and fellow eligible bachelorette Jennifer Aniston up for a date?
2. Naomi Watts
We were pretty broken up over the breakup between Naomi Watts and Liev Schreiber — they killed it on red carpets, were raising two cute kids, and taking on New York City. But all good things must (apparently) come to an end and the couple called it quits after 11 years.
Let’s call a spade a spade, breakups suck, but we bet it was made a lot easier for Watts and Schreiber to split without the hassle of divorce papers. The A-listers were never actually married, but we’d argue, and they probably would too, that nothing binds quite like kids, and these amicable exes will always be in each other’s lives (and maybe one day, back in love?).
3. Diane Keaton
Patron Saint of Single Ladies, Diane Keaton is in her 70s, has never been married, and is happy as can be. And why not? She has had/continues to have an incredibly successful career, raised two children, and Keaton rocks a suit better than most men.
She’s dated some high profile actors but Keaton is a-okay having never walked down the aisle with anyone, saying, “I don’t think it would have been a good idea for me to have married and I’m really glad I didn’t.” Keaton confesses she’s “an oddball” and she’s absolutely unapologetic about it. If only we could all age with that kind of confidence.
4. Charlize Theron
She’s an award winning actress, an active humanitarian, and on top of it all a mother of two — if Charlize Theron has time to go on a date, it should be held as a testament to how incredibly capable she is. That being said, the actress is open to a long term partnership, marriage however? Not so much.
Assuming some guy does manage to measure up to Charlize’s standards (and honestly, is any man good enough for our girl?), Theron has said on multiple occasions that matrimony isn’t for her, “…I don’t need to have a wedding. My heart and my life and how I am with that guy is going to be exactly the same.”
5. Kourtney Kardashian
We’re not trying to break up any happy couples out there, but we’re pretty sure we’re not alone in saying we really miss the days when Kourtney Kardashian and Scott Disick were reality television’s top couple. They may be dating other people these days, but we’re not sure we’re ready to give up on a possible reunion.
Together for nine admittedly tumultuous years, Kourtney and Scott have three incredibly cute kids together – can’t these two just work things out? Scott could pop the question on a Keeping Up With The Kardashians super special episode – we’re sure the ratings would be through the roof!
6. Queen Latifah
Rapper/actress/producer Queen Latifah has been in the spotlight for several decades, and despite all the details we crave about the lives of our favorite celebs, Latifah has managed to keep her personal life impressively private. If anything, the only thing we can say for certain about Latifah’s love life, is that we know she’s not married.
Rumors have been circulating for years now questioning Latifah’s sexuality and possible romantic partners, and somehow the public is still no wiser as to what’s really going on in her life. If and when Queen Latifah does get married, how long would it take for word to get out?
7. Tyra Banks
As the originator of “the smize,” otherwise known as smiling with your eyes, Tyra Banks sealed her place in pop culture history — the selfie generation really owes the supermodel an enormous debt. And it’s not just aspiring models that ought to look to Tyra as a role model, she’s got good advice for all the single gals out there too.
Banks isn’t exactly anti-marriage or anything, but she’s also not waiting around for anyone to be her end-all-be-all. “My mom never taught me to be waiting for some prince on a white horse to sweep me off my feet.” Banks is all smizes about her single status, successful career, and baby boy — she’s her own prince.
8. John Cusack
He’s played some of our favorite sentimental suitors, starting with Lloyd Dobler in Say Anything…, Rob Gordon in High Fidelity, and definitely Jonathan Trager in Serendipity, but John Cusack hasn’t had a romantic movie-like marriage of his own, and that’s okay! Marriage isn’t for everyone.
Whether or not Cusack is looking to tie the knot one day or not, he’s not talking about it — the actor is pretty private about his personal life. Truth is, we don’t care either way, he’s obviously a good enough actor to play the romantic lead, and we’re happy to live in la la land with Lloyd Dobler and his boombox.
9. Sarah Silverman
Funny lady Sarah Silverman wasn’t joking around when she declared how she feels about the idea of one day walking down the aisle, and is very much against making herself a Mrs. one day. Long term relationships are great, but according to Silverman, weddings are the worst.
Back in 2014 Silverman proclaimed that marriage is “barbaric,” elaborating, “Why would I want the government involved in my love life?” But before anyone goes and gets offended by her comments, she’s explained that she’s happy to watch others wed, but don’t wonder if she ever will – she really really wants you to know that she most definitely won’t.
10. Matt Dillon
Are we the only ones who would classify Matt Dillon as a man of mystery? He bounces between projects with seemingly no intentional trajectory, and as for his personal life? Well, since his split with Cameron Diaz in 1998, it’s as big an unknown as where or when you’ll next see him on screen.
Having once admitted that he’d be interested in one day settling down and starting a family, Matt Dillon hasn’t necessarily changed his mind on matrimony, but whatever he decides, it’s nobody’s business. “I don’t believe that my life has to be a model for anyone, I’m entitled to a life that’s not flawless.”
11. Leonardo DiCaprio
Leo, Leo, Leo, never change. Leonardo DiCaprio, the modelogamist (it’s a mix between model and monogamist and we’re standing by it) has been in some high profile relationships with some high fashion strutters, but at the end of the day, no one seems to stick. And we’re not shaming DiCaprio for being choosy – don’t settle!
Marriage is a serious commitment, and while Hollywood couplings haven’t gained a great relationship for longevity, looks like Leo prefers to be safe not sorry and maybe just not marry at all. Leonardo DiCaprio doesn’t seem to be lonely, and love is all you need in life. We all love you Leo, so keep at it, we’re on your side.
12. Oprah Winfrey
It’s not easy being Oprah, and having a strong support is important, which is why the media mogul is thankful to have a special someone by her side — and no, we’re not talking about her bestie Gayle King (this time). Oprah and Stedman Graham have been together for decades, and they don’t see that changing anytime soon.
In fact, Oprah seems certain that marrying Graham would have meant disaster,“What I realized is, I don’t want to be married…because I could not have the life that I created for myself.” Looking at the empire Oprah has built, with Graham at her side, who would dare say she should have done anything differently?
13. Kylie Minogue
We just can’t get Kylie Minogue out of our heads (or her hit song “Can’t Get You Out Of My Head”) and we’re all just wondering, how’s Kylie’s love life as of late? Asked and now answered: the Australian singer is single, happy and still very happenin’.
After breaking off her engagement to British actor Joshua Sasse, the singer is questioning accepting the proposal in the first place, saying, “I thought ‘Maybe I’ve got it all wrong and I should go for it.’” But looking back she’s sure that staying single is what’s best for herself, saying “I don’t think marriage is for me.”
14. Paris Hilton
Every child of the 90s still has a special place in their heart for Paris Hilton. Remember when she used to wear head to toe pink velour, because we’ll certainly never forget. And while few people remember her first fiancé Jason Shaw, who could forget that time Paris was engaged to Greek shipping heir, Paris Latsis.
Paris and Paris were the perfect pair. Or, they were for a few months. Most recently everyone’s favorite socialite got engaged to actor Chris Zylka, who popped the question with an impressive 22-carat diamond ring. But even Paris’ dream diamond wasn’t quite right for the star, so she’s single, and to steal her own catchphrase, “That’s hot.”
15. Jake Gyllenhaal
Singletons of the world take note, Jake Gyllenhaal may be single for now, but don’t expect him to stay that way forever. The actor told Howard Stern that he “loves love” and we all love him, so it seems like pretty simple math that the in-demand actor will be as in-demand in the dating world.
So why hasn’t the ever-charming Gyllenhaal said “I do” to anyone yet? He just hasn’t found the right girl, and we get that. “…I believe in monogamy I believe when you meet somebody who is right it will be right and you will stay there.” Jake, we’d like to say, you can stay with us anytime.
16. Jamie Foxx
Relationship conspiracy theorists rejoice! It finally happened! Jamie Foxx and Katie Holmes, who have been rumored to be in a relationship for years now, have at long last confirmed that they are indeed together by appearing on the red carpet of the Met Gala together in 2019. So next step, is down the aisle, right?
Wrong. Foxx still says, “I don’t know if I’m built for marriage…When it comes to connecting with somebody then being like there…I know I could be long term in our connection.” And it looks like he’s true to his word with Katie Holmes. No wedding necessary, we’re just rooting for these two.
17. Jon Hamm
Don’t get him confused with his iconic character Don Draper — Jon Hamm isn’t half as serious as his fictional counterpart. On Mad Men, Don was twice divorced, but the actor has never been married, well, legally anyway, we’re not sure what the rules are for common law marriages.
Hamm was in an 18 year relationship with fellow actor Jennifer Westfeldt, but they never actually made it official. Apparently it was for the best or they’d both be divorced, after the two went their separate ways in 2015. And as the child of divorce, it doesn’t matter who he’s with, Hamm is happy to skip the altar.
Surprised to find out that Shakira isn’t actually married? We don’t blame you, she’s been with Spanish footballer (soccer player to all the Americans out there) Gerard Piqué for 10 years, and the couple share two children. They’re clearly committed to one another, so why not make it official?
Well, like she sings, whenever, wherever, they’re meant to be together, and no piece of paper will change that. As far as the singer is concerned, she’s “semi-married.” Although it’s enough for them right now, Shakira says that if she does decide to marry, Piqué’s definitely the one, and as we know, Shakira (and her hips) don’t lie.
19. Marisa Tomei
Worried about bumping into your ex? Not Marisa Tomei, she’ll work with two former flames without batting an eyelash. Her longest-lasting love Logan Marshall Green, and ex-beau Robert Downey Jr. were both on the set of Spiderman: Homecoming and there’s no doubt there was no drama – Tomei is too cool for that.
Maybe it’s the fierce independence that comes from being a native New Yorker (riding the subway as a child instills a specific brand of boldness) but Tomei doesn’t feel she’s missing anything by not settling down. “I’m not that big a fan of marriage as an institution, and I don’t know why women need to have children to be seen as complete human beings.”
20. Winona Ryder
Despite Johnny Depp tattooing “Winona Forever’” to his upper arm during his three year engagement with Winona Ryder, the two would sadly not last forever (nor did the tattoo, which was famously edited to “Wino Forever”). But despite the devastation she felt after they ended, Ryder really thinks it was for the best.
Ryder’s happily dating her long-term beau, fashion designer Scott Mackinlay Hahn, and beyond that she’s not sure it’s worth the risk. “I’d rather never have been married than been divorced a few times.” And, according to the actress, and even director Francis Ford Coppola, she may have actually married Keanu Reeves on the set of The Guardian, so maybe she’s not so unwed after all?
21. Mary Louise Parker
Don’t go feeling sorry for Mary Louise Parker, she’s all the stronger for how her life has turned out. Splitting up from your boyfriend and the father of your unborn child, all while seven months pregnant doesn’t sound ideal, but ultimately, Parker’s made peace with the past.
Parker eventually went on to adopt another child, and has found her mission in life through motherhood. And as for men? Parker actually thinks her father is to blame for her pickiness in selecting a potential partner — he was just too good a father, her expectations are too high, “but you know what? That would be the least of my problems,” she says.
22. Sheryl Crow
There’s not much missing from Sheryl Crow’s life. She’s having fun fun fun raising her two sons by herself, songwriting whenever the single mom has a spare few seconds. That being said, she hasn’t shut herself off to the idea of marrying sometime in the future.
When her dream guy does come knocking, Crow has learned a few things she’d do differently her next time in love. “I think I would skip the engagement part [next] time, having been engaged a couple times. If I was that close to getting married, I would just go do it.” We like that decisiveness! Do it Sheryl, we support you!
23. Lauren Graham
Spoiler alert: Lorelai’s wedding to Luke in the bonus season of Gilmore Girls had us in tears. Watching those two tie the knot in the most whimsical wedding we’ve ever seen will satisfy our craving to see Lauren Graham as a bride, which is for the best because the actress isn’t interested in a walk down the aisle.
Graham has been dating actor Peter Krause for almost a decade now, but they don’t need to say “I do” to make it official, they’re married in their minds. While talking to Ellen DeGeneres Graham explained that what they have is “good the way it is.” If it’s good for them, it’s good for us.
24. Lucy Liu
We’d just like to say, Lucy Liu is a seriously cool lady. We love anyone who lives their life by their own rules, and that’s exactly what Liu did when she decided to have her son through a gestational carrier. Liu is taking on single motherhood with style, but she’s not entirely alone in life.
Liu has the support of a close group of friends for when the single mama needs a helping hand or a few hours off, and maybe even to go on a date? The actress is notoriously tight-lipped about her love life, but if her “nontraditional” path to motherhood is anything to go by, any relationship she’s in won’t be too conventional either.
25. Chelsea Handler
Oh Chelsea, may you never cease to surprise us with your outrageous, and hilarious antics. Bawdy comedienne Chelsea Handler hasn’t taken anything too seriously all her life, so why would anyone expect her stance on relationships to be any different? The funny lady is all about having fun, full stop.
After realizing that the stress of a big commercial wedding wasn’t required to be married, Handler has actually changed her mind on marriage. “So now I’d get married. Now that I’m single and have no viable options,” she said through laughter. We’re sure loads of dudes would be happy to date Handler, funny girls finish first.
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