These Superstars Have Avoided Marriage or been Singletons for so Long, that We’ve Forgotten Who They last Dated!
Even as we see many Hollywood couples who have lasted the test of time, there are plenty of famous examples of celebrities who choose to remain fabulously single and always wooing. They’ve avoided marriage like the plague, or have been single or widowed for so long, that they can’t remember the last time they dated someone!
Of course, these famous singletons can use dating apps and online dating services, but in reality, they never have any shortage of attention from admirers. But no marriage means no divorce attorneys, family lawyers or divorce settlements, so is that win-win for them?
Lets a look at the celebrity who have never been married or simply love their single status too much!
Queen Latifah, Age 50 – Rumored to be a New Mom and Engaged
As approachable and friendly rapper and actress Queen Latifah looks in real life and on screen, she is fiercely protective of her private life. So much so that we didn’t know that she was dating a gentleman by the name of Sean Moon in the 90s, until he was shot in a foiled carjacking incident on her automobile!
These days, however, the Beauty Shop actress is spotted with long time partner Eboni Nichols pushing a stroller! You see, after breaking up with her personal trainer Jeanette Jenkins, she was rumored to be engaged to Eboni, who was sporting a huge baby bump. In 2019, their son Rebel was born.
Adrienne Arsenault, Age 53 – Never Married
Canadian viewers of The National news program since 2017, know Adrienne Arsenault as the co-host and charismatic journalist who has been working as a senior correspondent with CBC News. Since 1991, when she joined CBC, she has steadily risen the ranks due to her hard work.
While Adrienne has had a very successful career in broadcasting, her personal life seems to be shrouded in mystery. She is said to be so career focussed, that she simply does not have the time to date! Or she’s just really good at keeping her personal life under wraps, as she is dating history is totally unknown.
Keanu Reeves, Age 55 – In a Relationship
This one’s a sad tale, really. Keanu Reeves, the star of The Matrix movies was in a serious relationship with actress Jennifer Syme between 1998 and 2000. They even has a child together, but she was stillborn, and this tore the couple apart and they split. Just a year later, Jennifer would pass away after crashing her car.
For the longest time, Reeves was devastated and could not sustain a relationship for long – allegedly paired with China Chow and Charlize Theron. But that was before he met Alexandra Grant in 2009. The visual artist collaborated with Reeves on the book Ode to Happiness, but they only made their relationship red carpet official in 2019.
Sheryl Crow, Age 57 – Single Mom of Two Adopted Sons
Singer Sheryl Crow’s most famous pairing has been with disgraced retired cyclist Lance Armstrong, who she dated for six years and he even gave her a diamond engagement ring. The ‘All I Wanna Do’ singer ended her engagement with Lance, but she has also dated other high-profile men.
In her file labelled “ past loves,” you will find the names of musician Eric Clapton, actors Owen Wilson and Josh Charles, producer Steve Bing and her own bandmate Doyle Branham II. But these days, she has no time to spend on dating apps, as she’s busy with child care… she has two energetic adopted sons to run after, as she is raising them alone.
Charlize Theron, Age 44 – Single Mom to Two Adopted Kids
If there’s ever an actress who is wholly and unapologetically single, it is Monster and The Italian Job star Charlize Theron. The South African beauty, with her signature charms and smile, has ruled the box office for many years now and is one of the top earning ladies out there. So why need a man to take care of her, right?
Theron has been linked to actors Keanu Reeves, Sean Penn, and Stuart Townsend, besides musician Stephan Jenkins, although she has never walked down the aisle in a wedding dress. She finds solace in her adorable adopted kids and is giving them the best upbringing in Los Angeles, even as she is busy making her movies.
Diane Keaton, Age 73 – Single for more than 3 Decades
Hollywood legend Diane Keaton is such a show-stealer that she has not needed a man by her side for 36 years, as she revealed in a 2019 magazine interview! The Annie Hall and Godfather actress has never wed, even though she has been linked to the who’s-who of Hollywood.
Her list of lovers (and some rumored lovers) include Woody Allen, Al Pacino and Jack Nicholson. One of her most public relations was with actor Warren Beatty, who she dated for 2 years but split after their movie Reds was released. Man or no man, Diane is one sassy diva!
Tim Robbins, Age 61 – Rumored to be in a Relationship
On the sets of their movie Bull Durham, a young Tim Robbins, who we know from the movie The Shawshank Redemption, met and fell in love with Dead Man Walking actress Susan Sarandon in 1988. Susan was 12 years his junior, and they moved in together shortly and had two kids, after which they split in 2009.
Seems like Tim prefers his romantic interests much younger than him, as he has been spotted in the company of the rather young Gratiela Brancusi. While the two do make for a handsome pair, and Tim may be wooing her with flowers, vacations and gifts, but it doesn’t seem like he will be tried down, as he has never been married!
Oprah Winfrey, Age 65 – In a Relationship
The Queen of Talk Shows and Media Mogul Oprah Winfrey had a very difficult childhood and strained family life. She had dated a few famous people before, like critic Roger Ebert and composer John Tesh. But when she met business owner Stedman Graham, she was finally home.
Oprah and Graham met at a charity donation event and started dating the same year that her famous eponymous show The Oprah Winfrey Show aired in 1986. While the show wrapped up a couple of years ago, the couple has been together for 34 years now. They were once engaged in 1992, but the wedding never happened and they called of their engagement even as they continued to date.
Betty White, Age 97 – Widowed
We can’t even imagine the shows The Golden Girls and Hot in Cleveland without the inimitable Betty White in it! With a record breaking 80 years in entertainment, this actress, comedian and producer has made a permanent place in all our hearts. And the diva is 98-years-young!
On the personal front, Betty’s first marriage to an Air Force pilot was a short lived affair, after which she married Hollywood agent Lane Allen, only to divorce him 2 years later. In 1961, she appeared on the game show Password and fell in love with its host Allen Ludden! They would end up marrying, but sadly, he passed away in 1981 from cancer and she has remained his widow ever since.
Kourtney Kardashian, Age 41 — Possibly Single
You’ve seen her on Keeping Up with the Kardashians, but unlike her sister Kim and Khloé who have been divorced already, big sis Kourtney Kardashian never got married! She does have her hands full with her TV show, businesses and her 3 kids, but she’s making the time to find the right guy for her.
Kourtney has been open that she doesn’t believe in marriage, and that’s why she never wed her baby daddy and long-time partner Scott Disick, who she dated for 9 years. She is now is the company of her on-again-off-again flame, model Younes Bendjima, who is much younger than she is.
Owen Wilson, Age 51 – Rumored to be in a Relationship
Owen Wilson is a slippery fish! Just when we think he’s found “The One” and is finally ready to get married, he’s single again. The Wedding Crashers star has had a slew of girlfriends, including his on-again-off-again flame actress Kate Hudson, who he dated for 3 years.
Oh, and Owen also has three kids from 3 different baby mamas. His first born’s mom is Jade Duell, who he split from in 2011. Then his on-again-off again relationship since 2011 with his personal trainer Caroline Lindqvist led of the birth of another son. And he last had a daughter from another ex, Varunie Vongsvirates. Owen is often spotted indulging in PDA with Lindqvist again these days!
Tom Cruise, Age 58 – Single
Mission: Impossible and Top Gun star Tom Cruise has an impressively long list of lady loves, who are surprisingly all famous people themselves — older, younger, same aged women included! There’s Cher, Melissa Gilbert, Heather Locklear, Cher, Penélope Cruz, Sofia Vergara and Laura Prepon.
Phew! That list includes more ladies, but only three of them have had the distinction of being married to him. He was previously married to actresses Mimi Rogers, Nicole Kidman and Katie Holmes, but all those unions ended in divorce. His last known girlfriend was actress Olga Kurylenko, who he dated in 2013, and has reportedly been single since then. We wonder, why!
Drew Carey, Age 62 — Possibly Single
Drew Carey is a very funny comic and actor who made us laugh with his improv show Who’s Line Is It Anyway? and then played host on the gameshow The Price is Right. While he generally hits Hollywood red carpet events alone, he has actually had a long list if lady loves who keep away from the media.
Drew was engaged to be married to two lovely ladies Nicole Jaracz and Amie Harwick. Both these relationships did not end up in marriage and later, sadly, Hollywood-based therapist Amie was found dead in her home. Drew is said to be single now, but we hope he finds love again soon.
Jon Hamm, Age 49 – Rumored to be in a Relationship
Even as he played the unfaithful playboy, Don Draper in his famous show, Mad Men, actor John Hamm is nothing like his on-screen character. For 18 years, he has been with actress Jennifer Westfeldt (Kissing Jessica Stein and Friends With Kids) and although they never had a formal marriage ceremony, they were as good as married.
But their relationship ended in 2015, when Hamm finally went to rehab for his alcoholism problem. This strained their relationship beyond repair, and they went their separate ways. He is now said to be dating his Mad Men co-star Anna Osceola after being spotted practically everywhere with her!
Tyra Banks, Age 46 – Single mom of One
Model and America’s Next Top Model Tyra Banks really surprises us with her long list of past boyfriends! Ever since she became the poster gal for diverse models all over the world, she has been getting attention from all quarters. She reportedly dated Rick Fox, Will Smith, John Singleton, and Seal.
One of her more serious relationships has been with businessman John Utendahl who she dated between 2007 and 2011. But her relationship with photographer Erik Asla (2013 – 2017) was at just another level, as she welcomed their child together, via surrogacy. Tyra has never been married, but she says her life feels complete now.
Cote de Pablo, Age 40 — Single
Cote de Pablo is famous for her on screen role as Agent Ziva David from the show NCIS, where she is mighty flirty with leading man Michael Weatherly. They might have had you convinced with their on-screen chemistry, but in reality, Cote was taken and in a long time relationship, but she never married.
The actress was dating Diego Serrano, of The 24 Hour Woman and Our Italian Husband fame. They were together for 15 long years until they ended it in 2015. The two only speak well of each other even today and she credits him for helping her step out of her comfort zone. We wonder who she is dating now!
Dana Delany, Age 64 — Single
Body of Proof and Desperate Housewives actress Dana Delany was adamant that she would be no house wife, or any kind of wife to anyone! Although the star has been in many relationships over the years, she just couldn’t be tied down.
Her known relationships include actor Henry Czerny, musician Don Henley, actor Treat Williams and writer Dave Holmes. Her name has also been associated with John Kerry, Michael O’Keefe and Robert Blake. Even though she exclaimed at age 50 that she was finally ready to marry, she remains single.
Shakira, Age 43 — In a Long-Term Relationship
With a glorious voice, amazing dancing skills and looks to kill, Columbian-born singer and performer Shakira has us all dancing to her tunes with her first English hit, Hips Don’t Lie. After that, she has had a string of successful albums and is one of the most famous Latina singers out there.
Someone along the way to success she met and was engaged to lawyer Antonio De la Rua, and the pair were together for over 10 years. He continued to manage her business after their split but ended up suing her for unpaid dues! Shakira still dodges marriage as she has been with Spanish footballer Gerard Piqué since 2011 and they have 2 kids together.
Rachel Maddow, Age 47 — In a Long-term Relationship
Rachel Maddow is the hilarious MSNBC host with her own show, The Rachel Maddow Show. Since 2005, she’s been a large liberal voice on TV and her political science degree makes her the best person to give us an insight into American and World politics.
Since 1999, she has been happily dating her partner Susan Mikula, who is an artist by profession. Maddow met her when she was doing odd jobs during her doctoral study break and worked on Susan’s backyard. They have been together since then, and Rachel credits her girlfriend for puller her out of her depression.
Simon Cowell, Age 60 — In a Long-term Relationship
Notorious Bachelor Simon Cowell may not be tied down with a marriage license, but he enjoys a great family life thanks to his long time love Lauren Silverman, who he has dated since 2009. They even have a son together, Eric, who was born to them in 2014.
The sharp tongued British producer and judge of shows like Britain’s Got Talent, America’s Got Talent, and American Idol, has had plenty of short relationships – 14 to be precise! Some famous names include Debbie Spears, Terri Seymour, Carmen Electra, and Tara Miller.
Lucy Liu, Age 51 — Single
Here’s a lesson for all the strong independent single ladies out there! Lucy Liu, who starred in hits like Charlie’s Angles and Kill Bill, has been in 5 public relationships so far, but when she in her late 40s, and single once again, she decided to not wait for a man to welcome her child via a surrogate.
Just a year before her son Rockwell was born in 2015, she was in a relationship with business owner and hedge fund manager Noam Gottesman. Before that she was engaged to movie director Zach Helm, and has been previously linked to George Clooney, Will McCormack, and Wladimir Klitschko.
Robin Roberts, Age 59 — In a Long-Term Relationship
Anchor and Newscaster Robin Roberts is the lady with the big smile who greets us on the show, Good Morning America on ABC network. But for 15 years before that, she worked as a sportscaster for ESPN. She usually keeps her private life away from the limelight, but that changed in 2013.
That was when she came out publicly and announced that she was dating massage therapist Amber Laign. And that’s not all, they have been in a relationship since 2005! All we know about Amber is that she is 14 years younger than Robin and had helped immensely when the anchor was undergoing cancer treatment.
Gerard Butler, Age 50 — Possibly Single
We can’t vouch for all the men from Scotland but actor Gerard Butler is one handsome Scot! And behind the star of blockbusters like 300 and P.S. I Love You, there have been many arm candies over the years, such as Lizzie Cundy, Chiara Conti, and Josie D’Arby, but only one constant – Morgan Brown.
He and Morgan have been in an on-again-off-again relationship between 2014 and 2016. He just couldn’t keep away from her and the couple rekindled their relationship in 2019. But Morgan is famous is her own right, as she was a model, and now runs in famous circles as she flips houses and is also an interior designer for celebs.
Matt Dillon, Age 55 – In a Relationship
Right after the movie There’s Something About Mary released, it’s lead stars Matt Dillon and Cameron Diaz split up after dating for 3 years. This isn’t the only high profile relationship the low profile actor has been in, as he has previously wooed actress Heather Graham.
We also found some really cute photos of a very young supermodel and actress Brooke Shields and Dillion together, when they were dating in the early 80s. Since 2015, he is said to be with actress Roberta Mastromichele, who starred in the 2010 Johnny Depp movie, The Tourist and 2009’s Nine. Matt and Roberta may be engaged, but there are no official announcements made as yet.
Mary-Louise Parker, Age 56 – Single Mom of Two Kids
She has lived her life with and without men, and she’s just fine either ways! Actress Mary-Louise Parker, who is known for her roles in Weeds, Red and Red 2, even wrote a book titled Dear Mr. You, about all the men in her life — those she knew intimately and some even fleetingly.
The actress has two children (a biological son and adopted daughter) but has never been married before. She was in a long term relationship with actor Billy Crudup from 1996 until 2003, when he cheated on a pregnant Mary-Louise with actress Claire Danes and left. Parker was also engaged to Weeds co-star Jeffrey Dean Morgan in 2008, but they split soon enough.
Winona Ryder, Age 48 – In a Long-term Relationship
Here is one famous face who is not a big supporter of marriage, as The Stranger Things and Edward Scissorhands actress Winona has never taken her vows! She jokes that she is technically “married” to work-husband Keanu Reeves, as a real priest performed their marriage on-screen in the 1992 movie Dracula!
In real life, though, she was in a serious relationship with Hollywood’s bad boy Johnny Depp for 3 years, and according to reports, even secretly dated actor Matt Damon. Since 2011, she has found love with fashion designer Scott Mackinlay Hahn, and they burn up the red carpet together often.
Marisa Tomei, Age 55 – Single
If you thought that the fabulous actors Robert Downey Jr., and Marisa Tomei looked very comfortable with each other on the screen in the movie Spider-Man: Far From Home, it’s because they way dated back in the 90s! They eventually broke up, but they still remain friends.
Shunning marriage in the future, too, the My Cousin Vinny actress chose to date the handsome Logan Marshal-Green in 2008. They were together until 2012 and then went their separate ways. Marisa has been previously linked to actors Christian Slater, Dana Ashbrook and singer-songwriter Lenny Kravitz.