Fabulous Single and Ready to Mingle – Maybe! – Celebs

Oprah Winfrey

Life hasn’t been easy for Oprah Winfrey, but she made it through the detours and roadblocks along her way. Now dubbed as the “Queen of All Media,” Oprah showed us she didn’t need a king to achieve what she has now. Not that we’re questioning her long-term relationship with her partner Stedman Graham, it’s just that marriage isn’t an option for the 66-year-old talk show host.

Oprah has been vocal that she doesn’t want to get married and that her career is her priority. Looking at the empire she has built, what more could she ask for? Oprah is North America’s first black multi-billionaire, and her net worth is now $3.5 billion. With that amount, she probably has many financial advisors to guide her.

Diane Keaton

Diane Keaton can be considered as one of Hollywood’s most elusive bachelorettes. Known for her idiosyncratic personality and style, Keaton is a successful Academy Award and Golden Globe Award winner for performances in films like The Godfather series, Play It Again, Sam, and Annie Hall.

The role was specifically written for Keaton, which can be seen in her performance. However, to avoid being typecast, she branched out to more dramatic roles in films like the Interiors, Reds, and Something’s Gotta Give.

Her personal life is almost as storied as her film career, with former beaus such as Woody Allen, Warren Beatty, and Al Pacino. Now that she’s getting older, Keaton remains adamant about not using marriage as an insurance plan and happily stays single with her adopted children.

Sheryl Crow

Sheryl Crow is a known voice to many. She’s an American singer-songwriter with ten studio albums with songs incorporating many genres. Like a smart financial advisor, she doesn’t put all her eggs in one basket and has since explored acting in shows like 30 Rock, Cougar Town, and Cop Rock.

Her career started way back in the late ‘80s and has since grown and changed over the decades, much like her personal life and relationships. In the ‘90s, she dated Eric Clapton, her senior of 17 years. After Clapton, she dated Owen Wilson, for whom she wrote Safe and Sound and other songs. Her last beau is Lance Armstrong. They were engaged at one point in 2005 but broke up in 2006.

Goldie Hawn

Goldie Hawn has a career that spans over sixty years, starting in the 1960s when she appeared in the Rowan & Martin’s Laugh-In television show before making it big as a Golden Globe Awardee of the Best Supporting Actress award for her performance in the film, Cactus Flower.

Although she doesn’t take as many projects as before, Goldie Hawn remains to be an institution in Hollywood with films like Private Benjamin, Overboard, and Bird on a Wire. Her storied career is almost as storied as her personal life. Unlike younger actors and actresses in this list, Hawn has made her investments in marriage twice – with Gus Trikonis and Bill Hudson.

Currently, she’s with Kurt Russell, who she has been with since 1983 but still hasn’t tied the knot with.

Jon Hamm

Jon Hamm may not be as dapper as his on-screen character after all. Best known as Don Draper from the AMC television drama series, Mad Men, Hamm took a while before coming to his big break. He started in the mid-’90s with small roles in TV series like Providence, The Division, and What About Brian.

Although this may be, it seems that he made investments in his skills thus landing the role of Don Draper for which he won Best Actor. However, it seems that fame took its price. He broke up with his long-term girlfriend, Jennifer Westfeldt, after almost two decades of being together.

However, who knows? Maybe his big break in love is just around the corner!

Matt Dillon

Matt Dillon has a career spanning more than three decades. He got his start as a teen idol in a film entitled Over the Edge, which was succeeded by a successful streak of other movies. He’s made investments in the industry with landmark films like On the Road and There’s Something About Mary.

Most of his relationships were known to the public but he still hasn’t tied the knot with any lucky lady. However, one of the most well-remembered of his affairs is his relationship with Cameron Diaz back in the ‘90s. They met when they were shooting different films in Minnesota. According to an interview with Rolling Stone, Matt said that it was long-distance that eventually ended their relationship.

Naomi Watts

Sometimes, serious long-term relationships still don’t end in marriage. Whether it’s a personal choice, a matter of finances including cash loans and investments, or what-not, some people just don’t prefer getting married.

The case may be applicable to Naomi Watts. The beautiful and talented British actress was in a long-term relationship with fellow actor, Liev Schreiber. The couple were together for eleven years and have two children together. Luckily, Watts and Schreiber remain to be friends and continue to co-parent their children peacefully.

Since the split, Naomi continues to produce beautiful films such as The Glass Castle, Luce, Twin Peaks, and the Divergent franchise. She also continues to be an active ambassador for the Joint United Nations Programme on HIV/AIDS.

Lady Gaga

This lady can really do it all. Given the number of songs and choreographies taking up her time, she still finds herself in serious relationships. As a matter of fact, she even met one of her former boyfriends on the set of a music video of one of her songs. She met Taylor Kinney in July 2011 and was, at one point, engaged to him.

She publicly spoke about their relationship in the documentary of her career, Gaga: Five Foot Two. After her break up with Taylor Kinney, Lady Gaga next felt the electricity of true love with Christian Carino. They were engaged as well but they broke it off back in 2019. Rumor has it, the reason behind the breakup was Bradley Cooper, Lady Gaga’s co-star from Shallow.

Kylie Minogue

Kylie Minogue is referred to by the European press as the Princess of Pop. She’s been in the industry with hits such as I Should Be So Lucky, and Hand on Your Heart. Her hard work and talent have won her different awards such as a Grammy, a Brit, and seventeen ARIA Music awards.

She’s also a cancer survivor. While she has the income to pay for her treatment, it’s best to assume that she also had her insurance to alleviate the bills. Given her battles and victories, it seems that marriage won’t be one of them.

Kylie claims that she’s not the type to get married but this doesn’t mean that she didn’t have long-term relationships. At one point, she was dating Joshua Sasse.

Lucy Liu

It seems that at one point in time, every young boy and man had a crush on Lucy Liu. As one of Charlie’s Angels, she played the role of Alex Munday. Another one of her iconic roles is Ren Ishii in Kill Bill. Aside from being a multi-awarded actress, she also made investments in films that she directed. Some of her works as a director include Meena and episodes for television shows such as Why Women Kill, Luke Cage, and Graceland.

Ever since her break up with none other than George Clooney, one of the most popular actors of all time, Lucy Liu hasn’t been with anyone since. She’s continued to be active in the industry with a Netflix film, Set It Up, while raising her child born through a surrogate back in 2015.