How to date someone older or younger than you
Relationship expert Dr. Ramani explains what to consider when dating with an age gap.
Kathy Griffin ended 2025 with the dating revelation that she fell in love with a 23-year-old man shortly after breaking up with ex-husband Randy Bick.
“I accidentally fell in love with a 23-year-old man,” the 65-year-old comedian wrote in an op-ed for The Cut magazine, published Dec. 31. “Because of his age, he didn’t have the sexism and misogyny and prejudice that you would expect from a man my age. He seemed to see me. I know that sounds really corny. Oh my god, it sounds so lame! But I felt so comfortable with him and so content just being around him.”
Although the relationship was short-lived, Griffin wrote that the two enjoyed each other’s company and have no regrets.
“When he told me he didn’t want to have kids and that we could be together forever, I knew he was too young. And I thought, ‘You don’t know that. You’re 23. You don’t understand anything,'” she wrote. “That’s why I had to release the pigeon.”
Griffin isn’t the only celebrity to pursue romance with men much younger than herself. After all, Bill Belichick and girlfriend Jordon Hudson, who have a 48-year age difference, officially announced their romance on the red carpet at the end of 2024. Katharine McPhee and David Foster, who have a 35-year age difference, got married in 2019.
Age-gap relationships are not necessarily uncommon, but they do come with complications that everyone involved should be aware of. Often the biggest challenge is not the relationship itself, but how the other person reacts to it.
“You have to be confident in your relationship” Janet Morrison, is a certified sex and relationship coach, previously told USA TODAY. “The biggest external factor influencing most of these relationships is not age, but the reaction and acceptance of the relationship by peers.”
Kathy Griffin and society’s obsession with age differences
Hollywood has a storied history of famous couples with notable age differences, such as Lauren Bacall and Humphrey Bogart (25 years apart) and Marilyn Monroe and Joe DiMaggio (12 years apart). In modern Hollywood, Kylie Jenner and Tyga (who met when Jenner was 14 and Tyga 21) and Florence Pugh and Zach Braff (21 years apart) have raised eyebrows, as has Scott Disick’s relationship.
Some people call their former older partner because they feel taken advantage of. Take Demi Lovato’s 2022 single “29,” for example, which was adopted by countless TikTok users who recalled their own past relationships. “Finally turning 29 / It’s funny, I’m just like you back then / I thought it was a teenage dream and it was just a fantasy / But was it yours or mine? 17, 29,” Lovato sings in the song, which is rumored to be a reference to ex Wilmer Valderrama.
When Taylor Swift, 36, re-released her 2012 album Red in 2021, she updated her breakup ballad “All Too Well,” which is said to be about actor Jake Gyllenhaal, who is nine years her senior, to include a reference to their age difference.
The media tends to portray age-gap relationships in a one-dimensional way. Wealthy, stable, older men have social, economic, and even sexual power, while attractive, young, and dependent “trophy wives” have only one thing to offer: beauty. Public debates about age-gap relationships can be brutal when older women date younger men, as evidenced by the label “cougar” that paints older women as prowling wild animals.
Commenting on the double standards older women face in age-gap relationships, Griffin said she is not ashamed of people calling her a “cougar.” In fact, she accepts it.
“I have never dated a man my age since I turned 30,” Griffin wrote. “So, people always say I’m a cougar, but I don’t care. I’m a cougar in a way. It means you have the freedom to choose who you want, as opposed to the age group that society tells you is your only choice.”
Relationship experts’ opinions on age differences
After all, for couples with an age difference to have a successful romance, it’s important that both people in the relationship see each other as equals.
The most common problem in age-gap relationships is when there is a toxic power imbalance. To avoid this, Meghan Gillen, a psychology professor at Penn State Abington who studies developmental psychology and body image, previously told USA TODAY that she advises people in age-gap relationships to be careful and assess the situation themselves. Ask yourself, “Does it feel appropriate? Do you feel comfortable? Do you feel like you can empathize with that person? Or do you feel like that person has power over you?” Younger partners in particular need to pay particular attention to potential gender, social, and power relationships.
Ian Kerner, a therapist and sex and relationship expert, previously told USA TODAY that for couples with a large age difference, it can be difficult not only to find common interests and activities, but also to integrate family and friends into each other’s lives. To combat this, Kerner says it’s important for the two of you to find fun things to do together.
Please remember. There are many examples of healthy and thriving relationships despite large age differences.
“Humans find connections everywhere,” Eric Anderson, a licensed marriage and family therapist, previously told USA TODAY. “Relationships shouldn’t be so judgmental as long as both parties can agree.”
Contributor: David Oliver
