Sheryl Crow
Sheryl Crow has never had much truck with the idea of a long-term relationship, seemingly happy living an independent lifestyle. Crow’s most famous relationship has been with cyclist Lance Armstrong, who she started dating in 2003. By 2005 the pair were even engaged, but they called it quits just a year later. Shortly after, Armstrong was involved in a major doping scandal. Crow remained single and has since adopted two children.
Oprah Winfrey
Oprah Winfrey is a self-made billionaire who has managed to rise from very humble beginnings. Winfrey does have a long-term partner, Stedman Graham, her significant other for approximately 30 years. There have been rumors regarding why the two have never married, with some even speculating that Oprah doesn’t want to have a messy, high-profile and expensive divorce should the relationship ever sour. But her friends would simply say that Oprah thinks, “If it ain’t broke, don’t fix it!”
Jacqueline Bisset
Jacqueline Bisset has attracted hundreds of men over the course of her adult life, and while she hasn’t shied away from relationships, wedding bells have never rung in her favour. Bisset’s last known relationship, with Turkish martial arts instructor Emin Boztepe, ended in 2008. As for children, Bisset has gone on record as not having them for their own sake. “I couldn’t in all conscience do what I do and have children,” she once said. “Could you imagine being the daughter of Raquel Welch? I’ve heard such horror stories, about the children in Hollywood.”
Mary-Louise Parker
Mary-Louise Parker initially found fame with films, but her TV roles, most notably in The West Wing and Weeds, cemented her legacy as an actress. Relationship-wise, Parker was involved with fellow actor Billy Crudup, with whom she had a child, before he left her for Claire Danes. Parker then met, began dating and got engaged to Jeffrey Dean Morgan on the set of Weeds. Their engagement was later called off and by all accounts, Parker has remained single ever since.
Chris Evans
If Captain America can’t find love, then honestly, who can? That’s right, Chris Evans is single (as far we know), and has been since the end of his last relationship to Jenny Slate in 2018. Prior to that, Evans had dated Jessica Biel from 2001 to 2006 and Minka Kelly from 2007 to 2014. In and around that, Evans has been on the touchlines of love, which is probably fantastic news to his legions of fans out there.
Jon Hamm
Jon Hamm, despite being a hot commodity in Hollywood in more ways than one, has been leading a bachelor life in recent years. From 1997 to 2015, he was in a relationship with actress and writer Jennifer Westfeldt. “We may not have a piece of paper that says we’re husband and wife, but after 10 years, Jennifer is more than just a girlfriend,” Hamm once said. Alas, the two never married or had children, and they split in 2015.
Coco Chanel
Born in a “poorhouse” at the tail end of the 1800s, Coco Chanel is one of the 20th century’s greatest success stories, having revolutionised the world of haute couture. Though she did enjoy a string of affairs over the course of her life, Chanel never settled down for good. One of her most infamous flings was with Hugh Grosvenor, the 2nd Duke of Westminster, who later tried to get her to negotiate a peace deal between Churchill and the Nazis. Chanel was a Nazi sympathiser who was involved with a party spy at the time.
Lady Gaga
Lady Gaga has had a few close calls when it comes to marriage and happy-ever-afters. Her relationship with actor Taylor Kinney seemed untouchable for a while, but Gaga broke the news of their break-up on her Instagram in 2016. She later shacked up with agent Christian Carino, who she also became engaged to. Sadly, things were not meant to be and the relationship came to an end. She has since been rumoured to be dating tech bro Michael Polansky.
Diane Keaton
Diane Keaton came to public attention in 1972 with the release of The Godfather. Around the time, she was dating co-star and on-screen partner Al Pacino, though the tryst petered out. She went to date a few more leading men: Jack Nicholson, Warren Beatty, Keanu Reeves. To this day however, Keaton remains happily unmarried, having once said: “Don’t think that because I’m not married it’s made my life any less. That old maid myth is garbage.”
Lucy Liu
Lucy Liu made simps drool in her portrayal of the ballsy and bloodthirsty head of the Yakuza, O-Ren Ishii back 2003’s Kill Bill. Before that, she’d starred in the rebooted Charlie’s Angels films. Despite her sex symbol status, Liu hasn’t attracted “the one”. She has a son, Rockwell, who was born in 2015 via gestational surrogate. “I was working and I didn’t know when I was going to be able to stop,” she said of the decision.
Matt Dillon
Matt Dillon seems like the kind of celebrity that would have had loads of kids with a high school sweetheart he met in 1974. The reality is a lot different. Though a fine addition to various films, there is one role that has always evaded Dillon: the doting husband. One of his most high-profile relationships was back in 1990s when he dated Cameron Diaz.
Danica Patrick
Danica Patrick may feel the need for speed but not so much the need to walk down the aisle and commit herself to one man for the rest of her life. When you’re literally the greatest female driver in history, petty relationships take a bit of a back seat. Patrick has enjoyed the occasional fling, though, two notable examples being NASCAR’s Ricky Stenhouse Jr and NFL quarterback Aaron Rodgers. As of 2022, Patrick is single and (possibly) ready to mingle.
Charlize Theron
Charlize Theron has long quashed any rumours of her waiting for marriage. After her most recent relationship with Sean Penn between 2013 and 2015, Theron told Howard Stern they were never even engaged, saying of such rumours, “That’s not true. I did not almost get married to Sean, that’s such bulls***. We dated and then we didn’t date anymore… it was for barely a year, he never moved in, I was never going to marry him, it was nothing like that.”
Tracee Ellis Ross
Tracee Ellis Ross was recently asked if she’d ever dreamed of having a large family, with the white picket fence and the bountiful breakfast served every morning. “Well, how could you not?” she said. “Our society spoon-feeds it to you. I used to put myself to sleep dreaming of my wedding. And I would still love all of that, but what am I going to do, just sit around waiting? Shut up. I’ve got so many things to do.”
Tyra Banks
Tyra Banks was one of the original Victoria’s Secret angels in its 90s heyday, earning about as much money as you can as a supermodel. She later made the jump to TV with America’s Next Top Model. Her most publicised relationship was with Norwegian photographer Erik Asla. In 2016, they had a biological son via surrogate. Unfortunately, the pair split a year later. Tyra has been linked to men recently though nothing has been confirmed.
Marisa Tomei
Marisa Tomei was in a relationship with Tom Hardy lookalike Logan Marshall Green between 2008 and 2012. Previous flings include Lenny Kravitz, Robert Downey Jr and Christian Slater. In the mid 90s, a Seinfeld episode saw Jason Alexander’s George Costanza jeopardise his own engagement in order to be with Tomei, to no avail. “I’m not that big a fan of marriage as an institution,” Tomei said in 2009. “And I don’t know why women need to have children to be seen as complete human beings.”
Jared Leto
Jared Leto is an actor, musician, and failed Joker. Known as a bit of a hippy hippy Californian cliche, Leto has had his fair share of fun when it comes to the ladies, dating the heady likes of Cameron Diaz and Scarlett Johansson. But as for endgame, no woman has tickled his fancy. Maybe that’s the key to his youthful skin: never marrying.
Allison Janney
“I’ve never had that instinct to have kids,” Janney has gone on the record as saying. “I’m at peace with it”. Sure, she’s had her share of relationships, but none strong enough to make an honest woman of her. She got engaged to Our Very Own co-star Richard Jenik in 2004 but broke up two years later. In 2012, she met production manager Philip Joncas. They dated for five years before breaking up in 2017.
Lauren Graham
Lauren Graham met Peter Kraus in 1995 on the set of Caroline in the City, but it wasn’t until they starred in Parenthood that they got together as a couple. They remained together for eleven years, but never married or had children. Graham has in the past called herself an observant Catholic so one can only presume that marriage is quite important to her.
Zac Efron
Zac Efron has been breaking hearts far and wide since being catapulted to stardom by the High School Musical movies, and as with any heartthrob, his love life has always inspired gossip column interest. Efron famously dated his HSM co-star Vanessa Hudgens and has also enjoyed trysts with such famous women as Michelle Rodriguez, Alexandra Daddario and Rebecca Ferguson, yet Efron appears no closer to tying the knot.
Joan Jett
Joan Jett may love rock’n’roll, but she has no interest in settling down with anyone, no matter how much it’d shut up journalists. The Runaways singer and guitarist has garnered a bad reputation for being deliberately private, refusing to confirm publicly where she falls on the sexuality spectrum, although it is widely believed she is either gay or bi.
Dana Delany
Dana Delany doesn’t care for your jibes, your sneering remarks about her absence of a conventional family life. In a 2017 interview, she even claimed she was “happily unmarried”, adding: “I do like relationships, but I have to admit. The older I get, the more I love my solitude. I don’t wanna give that up.”
John Cusack
“Society doesn’t tell me what to do,” John Cusack once said when pressed about his lack of a wife or children, which is precisely what you want to hear from an actor. A ludicrous, albeit true, rejection of peer pressure. Cusack hasn’t played by the rulebook throughout his career, both professionally and personally, though he has dated the likes of Neve Campbell and Minnie Driver.
Edie Falco
Edie Falco has had bigger fish to fry than worrying about going on the pull. In the past, she has faced more serious issues like addiction. Most importantly, she faced them alone, rubbishing the idea of a support network through any man. “Because I’m not married I tend to get a lot of eye-rolling conversations with people about their marriages,” she said. “Why would I want to head there? I want love in my life, no question about that. But I have a ton of it.”
Emilia Clarke
Emilia Clarke has spoken out about the difficulties of dating in the public eye. Of her relationship with Seth MacFarlane, she said: “Well, a con is you have strangers giving you love-life advice like, ‘I’m a big fan of the show, and I’m not sure what you’re doing with that guy,’ which I didn’t react well to. That happened in New York when Seth and I were together. This guy started to give me advice: ‘Can I get a selfie? And by the way…’ Uh-uh, bro.” Clarke has been linked to others in the film industry. No signs of wedding bells yet, though.
Owen Wilson
They say you can win a lady’s heart by making her laugh, and yet noted big screen funnyman Owen Wilson has not found anyone willing to walk down the aisle with him just yet. Infamously, Wilson came close to wedding girlfriend Kate Hudson, but wound up attempting suicide when she called it off. He also has three children by previous girlfriends.
Greta Garbo
Greta Garbo was as famous for her contributions to film as she was being Hollywood’s biggest ever recluse. Like many starlets of the time, she enjoyed numerous flings but never took a relationship further, once admitting to a reporter: “There are some who want to get married and others who don’t. I have never had an impulse to go to the altar. I am a difficult person to lead.”
Jane Austen
It is a truth universally acknowledged that any content writer will make the excuse to use Pride and Prejudice’s opening sentence in any article about or containing Jane Austen. This legendary novelist wrote fondly and authentically about the perils of romance, but never settled down herself. She was engaged once but changed her mind and called it off the next day.
Mindy Kaling
“In my 20s, I was not only boy crazy, but marriage and relationship crazy,” Mindy Kaling once revealed. “Now it’s almost the opposite.” In December 2017, however, Kaling gave birth to a daughter, Katherine Swait, followed by a son, Spencer Avu, in September 2020. She has never revealed the identity of the biological father. In 2022, she talked about being a single mother on Meghan Markle’s Archetypes podcast.
Louisa May Alcott
Louisa May Alcott’s decision to never marry was a lot more controversial in the mid-1800s than it is today, making her a special entry on this list. The beloved novelist behind Little Women, Alcott was once quoted as referring to her married friend’s “nest” as “very sweet and pretty, but I’d rather be a free spinster and paddle my own canoe.”
Condoleezza Rice
Condoleezza Rice has never been married or had children, which is very rogue for a member of the Republican party. Serving as the U.S Secretary of State during George Bush’s second term as president between 2005 and 2009, Rice is more known for her political life than her personal one, though she did date NFL player Rick Upchurch for a brief period before calling it off.
Kimberley Stewart
Rod Stewart may have had a string of marriages to his name but daughter Kimberley is yet to tie the knot. She has been linked to several celebs in her time, though, most famously actor Benicio Del Toro, who fathered her only child. The relationship was never officially confirmed but the hard evidence is right there.
Matthew Perry
Chandler Bing may have initially struggled to find love on Friends but Matthew Perry was doing just fine, boasting relationships with Baywatch’s Yasmin Bleeth and Pretty Woman’s Julia Roberts. But he’s yet to put a ring on any of his girlfriends. His longest relationship was with Lizzy Caplan, who he dated between 2006 and 2012.
Dina Meyer
Dina Meyer is an American TV and movie actress who first became famous in the 1990s on 90210, named after one of Beverly Hills’ five ZIP codes. A code Meyer hasn’t cracked, however, is the one of domestic bliss. No, Meyer doesn’t to seem so bothered by marital life. In fact, she doesn’t seem to bothered by dating life either. Not a lot is known about her relationship history. Could it be that she’s just… private?!
Naomi Campbell
Naomi Campbell shot to fame as one the new wave of supermodels that stormed the fashion industry at the end of the 1980s. As such, she caught the attention of many eligible bachelors, including Leonardo DiCaprio, Robert De Niro and P Diddy. In 1993, she became engaged to U2’s Adam Clayton but they separated the following year. She gave birth to a child in 2021 though the father remains anonymous.
Lauryn Hill
The Fugees singer and solo artist was with Bob Marley’s son Rohan for 15 years and a bunch of kids together, though they never married. It was for the best as they split in 2009 anyway amid rumours that Lauryn had gotten pregnant with another man’s child. She hasn’t been a public relationship since.
Emma Watson
Famous since the age of ten, Emma Watson has never known a life outside of media training. As such, she has virtually never spoken about her private life, though she has spoken about not speaking about her private life. “I can’t talk about my boyfriend in an interview and then expect people not to take paparazzi pictures of me walking around outside my home,” she once lamented. “You can’t have it both ways.” She has however been linked to the son of disgraced billionaire Sir Philip Green.
Colin Farrell
Irish Hellraiser Colin Farrell had no interest in settling down when he came onto the scene at the turn of the millennium. Why would he, when all of Hollywood’s delights are right there on a plate for you. Farrell did have a child, a son James, in 2003 among this initial chaos. He sobered up after filming Miami Vice and had another son, Henry, in 2009 with an actress he met on the set of Ondine. Since then, Col hasn’t been linked with anyone seriously.
John Mayer
Former player John Mayer is tired of your bullsh*t. Back in March, he spoke out mid-concert about the pressure on him to settle down. “‘When are you gonna find someone? You don’t want to have kids, do you?’ What the f**k have I done in my life to communicate that I don’t want to have kids? … What are you talking about?” The rant was unleashed in the MGM Arena in Las Vegas. Mayer has dated Jessica Simpson, Taylor Swift, Jennifer Aniston, Katy Perry, and likely countless others we’ve never heard of.
Shakira
Shakira may have devoted many of her years to relationships but she’s never been tempted to walk down the aisle and make it official. She met footballer Gerard Pique in 2010 on the set of the music video for her World Cup song Waka Waka (This Time for Africa). They stayed together for twelve years and had two children. “To tell you the truth,” she one said, “marriage scares the shit out of me. I don’t want [Gerard] to see me as the wife. I’d rather him see me as his girlfriend.” Shakira is currently looking at jail time for tax evasion so it’s not likely she’ll be spotted with a new beau anytime soon.
Eva Mendes
Eva Mendes has been living happily with Ryan Gosling since the met on set of The Place Beyond the Pines in 2011. They share two daughters born in 2014 and 2016. “I’m not, like, anti-marriage or the institution for other people,” she told Chelsea Handler in an interview. “I love the idea of a union, that’s very beautiful. I just don’t think it should be a piece of paper because society tells me to.”
Al Pacino
Al Pacino is one of Hollywood’s biggest screen icons. He’s charming, he’s successful, he’s rich. Why no marriage? Apparently the young Pacino made a vow to himself growing up in a broken home of Sicilian immigrants in the hardened Bronx that he would never marry. He has in the past proven, however, that he is capable and willing to “settle” down with the right woman. He had two children with National Lampoon actress Beverly D’Angelo between 1997 and 2003.
Kurt Russell
Kurt Russell and Goldie have one of the longest enduring relationships in showbusiness, yet have never been lured in by the pressure of putting a ring on it. “For people like us, the marriage certificate wasn’t going to create anything that otherwise we wouldn’t have,” Russell once said. The couple have appeared together in films like Swing Shift and Overboard.
Paul Thomas Anderson
Paul Thomas Anderson is the critically-acclaimed director of Punch-Drunk Love, Magnolia and There Will Be Blood. He’s also the boyfriend and actress and comedian Maya Rudolph, with whom he shares four children. Despite not tying the knot, Rudolph still refers to Paul as her husband. “People know what that means,” she explained. “It means he’s the father of my child, and I live with him, and we are a couple, and we are not going anywhere.”
Leonardo DiCaprio
This is hardly shocking news, is it? Leonardo “Supermodel Addict” DiCaprio. Leo “Hump and Dump” DiCaprio. He has, of course, given a vague, nothing excuse for his lack of domestication to the press at times. “The truth is,” he once revealed. “You can’t predict marriage. You can’t plan it. It’s just going to happen when it happens.” But the thing is, you can plan marriage. In fact, there is probably nothing more planned in this life than a marriage. If you don’t plan a marriage, they don’t happen. Simple as that.
Enrique Iglesias
I can be your hero, baby! I can kiss away the pain (oh yeah!) I can stand by you forever! Except down the aisle, in a nice suit, with a ring in his palm. That is something Enrique Iglesias has no plan on doing when it comes to his long-standing relationship with tennis legend Anna Kournikova. “We’ve been together for 17 years,” he once said. “So what’s the difference? I believe in marriage, but whether we’re married or not, it wouldn’t make such a big difference.”
