Ann Coulter, 58 – Single
According to Coulter’s friend, Kellyanne Conway, Coulter started dating her security guard because there is no one else for her to date. The fiery writer and lawyer has gotten under many people’s skin with her far-right sentiments, often to the detriment of her love life.
But she has been in relationships and has been engaged many times. Some of her relationships include Spin Magazine founder Bob Guccione Jr and writer Dinesh D’Souza. Coulter was even recently linked to actor and comedian Jimmie Walker, but Walker has since denied this, saying that they’re just good friends. She may not have a husband, but at least she has two friends.
Sheryl Crow, 58 – Single
Sheryl Crow once wrote a song called Love Is A Good Thing, and she has practiced what she preached, finding love on several occasions. The only thing is she’s never turned one of her relationships into a marriage. Crow came close when she got engaged to retired cyclist Lance Armstrong, but they broke off their engagement after two years.
She also dated in various circles and once was involved with guitar supremo Eric Clapton, even though they had a 17-year age gap between them. Crow also once had a romantic relation actor Owen Wilson, who she dedicated a song she wrote called Safe and Sound to.
Bill Maher, 64 – Single
It’s not that Bill Maher isn’t married yet. It seems like he doesn’t want to be married at all. He even admits on his website that he is the last of his guy friends still unmarried and doesn’t get to play with them much because of that.
Queen Latifah, 50 – Rumored to be Engaged
Queen Latifah can talk. She does it in her movies, she does it in her rap albums and even started her talk show called The Queen Latifah Show from 2013 to 2015 so that she could talk. The one thing she doesn’t talk about, though, is her love life. But there has been speculation.
Latifah, who has never been married, once dated her trainer Jeanette Jenkins for nine years. They broke things off, and eventually, in 2013, Latifah started dating dancer Eboni Nichols. Their relationship appears to be on and off again, but they do share a child born in 2019. They’re rumored to be engaged.
Keanu Reeves, 55 – In a Relationship
Whether as Ted “Theodore” Logan or as Neo, Keanu Reeves’s film storylines always have the fate of the world at stake. This is probably why the actor and philanthropist is such a hit with the ladies. At one point, he had dated Charlize Theron and Sandra Bullock, both of whom he starred with in films.
Reeves has never been married though. But he is in a relationship with artist Alexandra Grant, officially since 2019, although the couple met in 2009 and collaborated on a few books. Reeves is currently busy and set to save the world again as Neo in Matrix 4 and Ted in Bill and Ted Face The Music.
Betty White, 98 – Widowed
Everyone’s favorite Golden Girl, Betty White, has been married three times in her long life but hasn’t married again since she lost her last husband, Allen Ludden, in 1981. White appears to have no intention of marrying again as she was once quoted saying, ‘when you’ve had the best, who needs the rest.’
Oprah Winfrey, 66 – In a Relationship
So the queen of all media has never been married, but she has had her fair share of relationships that have, in many ways, shaped her into the strong woman she is today. Many of her relationships were either abusive or drug-fueled, and she attributes that to her weight issues in the early part of her career.
Seth MacFarlane, 46 – Single
Seth MacFarlane hasn’t written off the idea of marriage, but between Family Guy and American Dad, it seems he is too busy for almost anything, nevermind romance. There was a significant relationship he’s had, that’s with Game Of Thrones star, Emilia Clarke.
Things didn’t work between them (Seth was probably too busy), but they’re still on good terms. That was in 2013, though, and he has been very private about his relationships since them. But it was reported in May 2020 that he had broken up with artist, singer, and alleged genius Semenona Martinez. They had been dating for four years.
Jon Hamm, 49 – Allegedly in a Relationship
Actor John Hamm and actress Jennifer Westfeldt started dating in 1997 before any of them had made it big. Together they achieved their success, particularly Hamm, who got his breakthrough role in Mad Men. They even opened a production company together and also adopted a dog.
Then in 2015, they released a joint statement announcing their separation. The announcement came after Hamm got out of rehab for alcohol addiction, and 18 years after they started dating. In June 2020, it was reported that Hamm was back in the dating game with former co-star Anna Osceola.
Tyra Banks, 46 – In a Rumored Relationship
How is one of the world’s most recognized supermodels not married? Well, it’s not like she is the only unmarried catwalk superstar, and Tyra Banks is renowned for not being in many relationships. She has been in a few relationships, most notably with photographer Erik Asla.
The two share a child, conceived and birthed via a surrogate in 2016, but their relationship didn’t last. Banks has been outspoken about her previous abusive relationships. It was reported in 2019 that she had moved in with Canadian Businessman Louis Bélanger-Martin. Banks also hinted at having another child, saying her mother wants more grandchildren.
Tom Cruise, 57 – Single
Tom Cruise is no stranger to marriage. He just hasn’t been in one for eight years. And he’s been married for extended periods as well. His first marriage to Mimi Rodgers was the shortest at three years. His second marriage was to Nicole Kidman, his longest at 11-years. Then there was his marriage to Katie Holmes, which was six years.
His last marriage ended in 2012, and he hasn’t been very active since. But in 2019, rumors surfaced that he was in a relationship, set up by the church of Scientology, with Handmaid’s Tale star Elisabeth Moss. Moss recently debunked the rumors in a 2020 interview with Andy Cohen.
Kourtney Kardashian, 41 — Possibly Single
It’s hard to believe that after dating on and off for nine years and sharing three children, that Kourtney Kardashian and Scott Disick never married. Although, if you’ve watched Keeping Up With The Kardashians, you may have a different opinion.
Monica Lewinsky, 46 — Single
Monica Lewinsky will probably always be remembered for the scandal that rocked the Whitehouse in the mid-’90s, where her “inappropriate relationship” with then US President Bill Clinton became public. Despite her role in the scandal, Lewinsky has moved on and is now an activist, fashion designer, and writer.
She never married, and there isn’t any news about her relationships, although there was a rumor that she dated writer Jeff Boggs after the scandal. But after escaping the limelight by studying in the UK, she returned to America and started her new chapter as an anti-bullying advocate.
Lucy Liu, 51 — Single
Lucy Liu has chosen to be a single parent. She has a son that was birthed by gestational surrogation named Rockwell and is a huge advocate of multidimensional family structures. But does that mean she doesn’t ever want to be married?
Well, she has tried and was even engaged to writer and director Zach Helm. Their dream wedding never materialized, but Liu kept looking for love and had a three-year relationship with the actor will McCormack and a four-year stint with Israeli-American tycoon Noam Gottesman. She was even rumored to have dated heavyweight champion boxer Wladimir Klitschko. Lucy Liu is still a single mom in 2020.
Simon Cowell, 60 — In a Long-Term Relationship
If you’ve watched Idols or America’s Got Talent, you know that Simon Cowell has a reputation for being a bit harsh. You’ll probably also wonder what kind of women would want to be with him. But he is quite the ladies man and has had his fair share of relationships.
Drew Carey, 62 — Possibly Single
If you put Drew Carrey on paper, he would be the perfect marriage material. He’s funny, had a show called Whose Line Is It Anyway, so can improvise and is also tough as nails since he was in the US Marine Corp. But despite these positive, he has never been married.
Carrey has tried, though, and was engaged to Amy Jaracz in 2007 and later on to intimacy therapist Amie Harwick. But somehow these weddings never materialized, although he is still close to Jaracz’s son, who sees him as a father figure. In February 2020 Harwick was found dead in her apartment, her boyfriend was eventually arrested as a suspect.
Shakira, 43 – In a Long-Term Relationship
Colombian Pop queen Shakira and decorated soccer star Gerard Pique have been dating since 2011, a year after Pique won the Soccer World Cup. Surprisingly, and despite always being in the public eye, the two have never married. They do have two children, though.
Before then, Shakira was in a relationship with Argentine lawyer Antonio de la Rúa. She once said that their relationship was like a marriage, and they didn’t need papers for it. In August 2010, they announced that they were splitting by mutual consent. Shakira is gearing up for another world tour in 2021.
Robin Roberts, 59 – In a Long-Term Relationship
Robin Roberts has had many ups and downs in her life. She has been inducted in the WNBA Hall of Fame for her contribution to the women’s game. Roberts has also been diagnosed with breast cancer, and bone marrow disease on separate occasions. But she beat both diseases, and with long time partner amber Laign by her side.
TV host Roberts and Massage Therapist Laign started dating in 2005, and, although not married, have had each other’s backs devoutly. Roberts eventually went public about her orientation in 2013, although those closest to her were already aware. She earned a Peabody award for the coverage of her bone marrow disease treatment.
Gerard Butler, 50 – Possibly In A Relationship
Who doesn’t want an action hero with a sense of humor for a husband? Well, as far as Gerard Butler goes, there are at least 23 known women who have tried. Some of the women linked to him include Cameron Diaz, Madalina Ghenea, Brandy Glanville, and Jeniffer Aniston.
Rachel Maddow, 47 – In A Long Term Relationship
Rachel Maddow is renowned as a liberal commentator and as the host of the Rachel Maddow show on MSNBC. She has also been in a 21-year relationship with artist Susan Mikula. Although they’re not married, the couple has been through a lot together.
They met in 2009 while Maddow was studying, and some of the challenges they’ve had included Maddow Cyclical depression. She went public with her issues in a 2012 interview, saying that it helped her to learn from other survivors through coming out about it. Gay marriage has been legalized since 2015. Maybe we’ll finally see Maddow married.
Matt Dillon, 56 – In a Relationship
Matt Dillon may have been living the bachelor’s lifestyle for most of his life, but in a 2006 interview, he said he was still open to marriage. Some of his relationships include the early ’80s romp with Brooke Shields, a fling with Melanie Griffiths, and a three-year relationship with Cameron Diaz, who starred with him in There’s Something About Mary.
But Dillon has never been married although he has been seen around with Italian actress Roberta Mastromichele. Dillon starred in the 2020 film Capone, alongside Tom Hardy. The film was released on several major digital platforms after the COVID-19 lockdown prevented a theatre release.
Maggie Smith, 85 – Widowed
She may have taught a bunch of film wizards how to wingardium leviosa, but acclaimed actress Maggie Smith hasn’t been floating on air in a long time. She married twice in her life: once to Actor Robert Stephens, with whom she had her two sons but later divorced. The second time with playwright Alan Beverly Cross.
Cross, however, died in 1988 at the age of 67, and Smith hasn’t married since. Despite not having a husband, the Oscar-winning actress has said that it’s pointless not sharing life with someone. Smith could have been referring to some secret partners, or her two sons and five grandchildren.
John Cusack, 54 – Single
John Cusack may not be a Hollywood heartthrob, but he is still a hit with the ladies and has dated the likes of Minnie Driver, Neve Campbell, Jennifer Love Hewitt, and Uma Thurman. Cusack is such hit with the ladies he was even stalked by one named Emily Leatherman, who was arrested in front of his home in 2008.
But despite his success in the relationship department, he hasn’t managed to score in the marriage department. It seems that Cusack doesn’t mind, though. In 2009, when asked about getting married and why he hasn’t, Cusack vehemently answered that society wouldn’t tell him what to do.
Mary-Louise Parker, 55 – Single
Mary Louis Parker has not had the rub of the green when it comes to men in her life. She was famously left by actor Billy Crudup, who went on to date Claire Danes. Later in 2006, she would meet actor Jeffrey Dean Morgan.
Parker and Morgan even got engaged in 2008. But, just before they were meant to marry, they broke off their engagement. These days Parker is happy with her two children, one for Crudup and the other adopted before she and Morgan broke up. She is set to reprise her role, Nancy Botwin, in a sequel to the hit series Weeds.
Jack Nicholson, 83 – Single
When you’ve been around as long as Jack Nicholson, you’re bound to have a long list of lovers. Nicholson was married to Sandra knight for six years in the ’60s but never married again after he divorced her in 1968.
He did, however, have some high profile relationships with the likes of Anjelica Huston, Rebecca Broussard, and most recently, Lara Flynn Boyle, among others. His unmarried relations have also garnered him, five children, including Lorraine Broussard Nicholson, who is also an actress. Nicholson retired from acting in 2013. He appears to have retired from romantic relationships as well.
Winona Ryder, 48 – In a Relationship (and possibly married to Keanu Reeves)
Winona Ryder stepped back in the big time when she starred as irate concerned mother Joyce Byers in the Netflix series Stranger Things. It took her back to the days when she was starring in films like Beetlejuice and Edward Scissorhands and dating Johnny Depp and Matt Damon.
Ryder was engaged to Depp in the early ’90s, but they broke up before they could reach the altar. She is currently dating actor Scott Hahn, but it was recently revealed that she might be married to Keanu Reeves. The two had a wedding scene in 1992s Dracula, with a full wedding ritual done by a real Romanian Priest.
Leonardo DiCaprio, 45 – In a Relationship
Let’s get this out of the way nice and early, Leonardo Di Caprio has never been married because he’s always looking for a younger partner. This was proven by a chart posted by a Reddit user claiming that Di Caprio has never dated a woman older than 35, and the average age of his partners is 22.9.
They all also apparently must be supermodels, as the list of names like Kristen Zang, Gisele Bundchen and Bridget hall show. His recent partner is a change though: she’s still under 25, but she’s an actress instead of a model. Di Caprio recently starred Quentin Tarantino’s Once Upon A Time In Hollywood.
Jacqueline Bisset, 75 – Single
Actress Jacqueline Bisset came straight out and said she never married because she didn’t want to deal with the bad habits of a long relationship. Funnily this didn’t stop her from having long relationships, and she pursued quite a few in her heyday.
Bisset shot to fame in the sixties and had several lengthy relationships with actors like Michael Sarrazin for six-year, and Russian dancer Alexander Godunov for seven and more recently two stints with Emin Boztepe that totaled 12 years. She may not be looking for relationships at the moment, but at 75, she is still working and has an upcoming film called Birds Of Paradise.
Ricky Gervais, 59 – In a Relationship
It could be his career or his atheist views. But Ricky Gervais has never felt the need to be married. He has been in a relationship with producer and author Jane Fallon since 1982. Even being together for nearly 40-years doesn’t matter, because as British citizens, they are not subject to common-law marriage.
But the are a couple who have been together for a half a lifetime. Strangely, Gervais and Fallon have opted against having children as well, saying that they didn’t want to dedicate 16-years of their life to children, and merely saying that there are enough children in the world.
Kristin Davis, 55 – Single
In her role as Charlotte York Goldenblatt in S** and the City, Kristen Davis was married twice. In real life, Davis has never married, and according to an interview she did in 2013, she was too busy to think about being in a romantic relationship.
Davis has dated actor Leiv Schreiber and screenwriter Aaron Sorkin. She has also been linked with actor Damian Lewis and Rick Fox as well as photographer Russell James. The irony of all of this is that Davis hosted the Fox dating gameshow Labor of Love, where a woman is looking for the perfect man to start a family with.
Laura Ingraham, 57 – Single
Laura Ingraham may not have been married, but she does have three children. The girl and two boys were adopted between 2008 and 2011, and keep the talk show host busy enough to not think about love and marriage. Of course, that doesn’t mean she’s out of the dating game.
Ingraham dated her co-worker and sports commentator Keith Olberman, and also had a relationship, that turned into engagement, with Author and filmmaker Dinesh D’Souza. They never married, but she defended him in court when he was being tried for fraud. They remain, friends, even after other conservatives turned against him for his controversial tweets.
Charlize Theron, 44 – Single
Oscar-winning South African born actress Charlize Theron has played married women in plenty of her movies. But she has never been married in real life. Theron has, however, been in a few high profile relationships. Including sweet November co-star Keanu Reeves, and Third Eye Blind frontman Stephan Jenkins.
She was also in a high profile relationship with fellow actor Sean Penn, but they eventually broke up in 2015. Theron will star in Superhero film The Old Guard and is also up for reprised her role as Cipher in the Fast and Furious franchise.
Marisa Tomei, 55 – Single
Wonder why the MCU Aunt May and Tony Stark had such a steamy hot on-screen chemistry? Because Oscar winner Marissa Tomei and Iron Man Robert Downey jr once dated in the early ’90s. Their friendship lasted longer than their relationship did, and it was Downey Jr who put her name forward for the role.
Tomei is pretty tough about marriage, saying she’s not a fan of it as an institution. She also says she doesn’t see why women must have children. Tomei has been in a relationship with actor Logan Marshall-Green from 2008 to 2013. She can be seen in the 2020 film, The Kings of Staten Island.
