Fourth Time’s the Charm? How the Dating Industry Can Give Hope to Singles With Multiple Divorces

Beauty, talent, and wealth: These are among the most highly-valued qualities in our society, and yet, they don’t guarantee romantic success in life. The 673,989 couples who initiated divorces and annulments in 2022 could probably attest to this. 

One of Hollywood’s biggest and brightest stars, Halle Berry, possesses all of those qualities, but has still gone through three divorces. The actress, director, and producer recently opened up about her experiences with divorce, and her perspective sheds light on the thousands of other women who have gone through it, too. 

“I found my guy later in life,” Berry told Drew Barrymore during a recent appearance on the latter’s talk show. Berry and current boyfriend, musician Van Hunt, met in 2020. Berry opened up about how her experience as a multi-divorcee has changed the way people see her — and the way she sees the dating world. 

Barrymore, who has also been divorced three times, asked Berry how people meet these days. “It’s hard in these streets,” Berry said. “I’ve heard people say, ‘Something must be wrong with Halle Berry, she can’t keep a man.’” 

There’s so much stigma surrounding divorce, especially multiple divorces, that even beautiful, successful celebrities like Berry and Barrymore have trouble overcoming it. 

The dating industry has the opportunity to reach out to these divorced singles with new resources and representation, not to mention hope. 

Divorcees Deserve Representation in the Dating World 

Of course, not every divorcee wants to get married again. In 2013, only 15% of previously married women surveyed by Pew said they were interested in getting remarried, while 54% had no interest in it. It’s easy to understand why. Sixty-seven percent of newly divorced women surveyed by Worthy said they were worried about picking the wrong partner, and 68% of women were flat-out scared about dating again. 

A lack of representation for divorced women in the dating world may perpetuate the idea that divorce is a sign of failure. “Who’s to say I want to keep a man?” Berry told Barrymore. 

“In the U.S., the most sentimentalized and celebrated families — nuclear families comprised of married parents and their children, and no one else — account for fewer than 20 percent of all households. The way we live now is limited only by our imaginations,” Bella DePaulo, Ph.D., said for Psychology Today. Divorce rates may have declined in recent years, but they aren’t non-existent. With this in mind, the dating industry could do more to destigmatize divorce. 

“Getting divorced can be an affirming, loving, and even life-saving thing to do,” DePaulo added.

If Halle Berry has had trouble finding love as a multi-divorcee, then chances are the average woman has had trouble, too. There are more divorced singles looking for love — or for hope — than industry professionals may think. 

Dating Platforms Can Be More Receptive To Divorced Singles 

Berry’s observations suggest that the dating industry could be more inclusive of divorced women, particularly those who have been divorced more than once. Despite some groups of women saying they worry about future relationship failures, 68% of newly-divorced women surveyed by Worthy said they were excited, even optimistic, about dating again, even if marriage wasn’t the end goal.  

Berry has said that her own experiences with divorce made her more reflective of her dating habits, and solidified what she really wanted in a partner. “I don’t want to keep the wrong man. Like, I’m not crazy, right? So when you find that you make a mistake — we all make mistakes. We have a right to say, ‘Oh God, this was a mistake. Let me start again.’ We have the right to do that,” she told Barrymore. 

Women like Berry who have gone through more than one divorce understand the dating industry’s limitations — and its opportunities — better than anyone. They would most likely benefit from dating resources such as counseling, inclusive online dating services, and even coaching. In her interview with Barrymore, Berry credited her manifestation techniques for nabbing her current beau, Van Hunt. 

“What I realized was when I manifested the last time, I only focused on what I wanted. The things I didn’t want I didn’t even think about,” she said. “I was very specific about what I needed. I would just be positive around it, and believe it or not, one day I got introduced to him by a friend.”

Obviously, not every woman has mastered the art of manifestation. Instead, dating platforms that acknowledge how a divorced woman deserves a second (or third, or fourth) chance at love can make the transition into dating easier, and therefore more enjoyable, for divorced women. Input from dating experts can even help divorced women learn more about themselves and what they can do differently, if anything, next time around. 

“I had never been that intentional with my relationships. I was loosey-goosey with that,” Berry told Marie Claire. “You have to be clear with the universe [or] any old thing will find you.” Or, as any dating professional would say, you can put all of your clear intentions into a dating app or dating service that can streamline the love-seeking process for you. 

Berry Offers Hope To Divorced Women 

Fifty-nine percent of divorced singles told Worthy that they rely on a dating app or platform to make romantic connections. In fact, connecting over an app or over the phone may be easier for some people, especially if they’re hesitant about starting a physical relationship. In an interview with AARP: The Magazine, Berry explained how she and Hunt first got to know each other while talking on the phone over a four-month period during quarantine. “We were forced to let only our brains connect and discover if we had a connection before our bodies decided to get involved,” she said. “I’d never done it this way. I fell in love with his mind, his conversation.”

People with multiple divorces may require more encouragement, more patience, and more confidence — three things the dating industry isn’t always known for providing. Berry, however, has made it clear that support, patience, and time have made it possible for her to finally find the love of her life after three divorces. 

“To all the Valentines who may be struggling to get it right … I feel you, but never give up and NEVER SETTLE for less than what makes your heart sing!” she wrote on Valentine’s Day, 2021. She took to Instagram to give hope to disgruntled daters and conflicted divorcees. “No matter what they say or what they call you. No matter how many times you try, it’s always worth it. If you desire love, you will find your match, your equal … your person … even if it takes you until you’re 54!” 

The hope has spread: In 2025, Berry wrote a sweet message to Hunt on Instagram to celebrate his birthday, and one of the top comments on the post came from a fan: “Your relationship made me want to fall in love again,” they wrote. “I thought I was too old to feel butterflies again. It may be possible after all.”