Man or Woman, Straight or Gay, Dating After 40 is Not For The Weak Hearted

Gina Cherelus

By Gina Cherelus

In the Third Wheel column, Gina Cherelus explores the delights and horrors of sex, dating, and relationships.

The New York Times

 

By the time Winter Harris was in her early 40s, she had begun to accept a reality in which she might be single for the foreseeable future.

After two failed marriages and a handful of bad dates, Ms. Harris, a marketing and communications consultant in Washington, D.C., had become more at peace with the idea.

“Clearly the dating pool has pee in it, and this is going to be my life,” Ms. Harris, 42, said.

Daters over 40 are not a monolith. But in conversations and online, there’s a consistent subtext to accounts of their experiences: The stakes are higher. There’s a common fear that once you reach your 40s, the likelihood of finding the kind of love that spawns butterflies grows slimmer and slimmer.

People dating in their 40s might complain about the ever-changing dating terms and dynamics. They might point to their specific circumstances — parenthood, divorce, death, work — as evidence of why it’s so hard to find a suitable mate. 

Ms. Harris, who married her first husband at 19 (they divorced about 15 years later) and her second husband at 38 (they divorced within a year), said she was “low-key traumatized” by her return to the hunt. “It just really opened my eyes to how different the dating world was,” she recalled.

 

There are many examples of people finding love after 40, despite the struggles that come with middle-aged dating. Vice President Kamala Harris and her husband, Doug Emhoff, speak frequently — including, most recently, on the stage of the Democratic National Convention — about how they fell in love after meeting on a blind date when they were both 49.

When Kristine Natural, 44, started dating again after divorcing her spouse of almost 10 years in 2021, she approached the process with new clarity and higher standards. Ms. Natural, who works in data analytics and lives in Houston described her marriage as mostly sexless and said she regretted overlooking early warning signs like a lack of intimacy when she and her former spouse were still dating.

Not long after her divorce, Ms. Natural began using dating apps to test the waters and found the experience to be overwhelming. She had one match she thought might be a serious connection, but the man eventually ghosted her. Another match didn’t immediately disclose that he was married. And like many women, she has received her fair share of unsolicited explicit photos. 

Ms. Natural, who is currently single, said that she enjoys going out to restaurants and bars by herself as well as solo travel. “At the same time,” she added, “it would be nice to have your soul mate you could go home to.”

“Overall, I’m in a good spot,” she continued. “It’s not something that I lose sleep over.”

Cody Buckalew, 41, re-entered the dating pool last year after his wife of five years died from cancer. Mr. Buckalew, who has a 2-year-old daughter and lives in Phoenix, said that he began exploring dating apps around the anniversary of his wife’s death.

“I downloaded Tinder because that was the only one that I knew of and I quickly got off that because I was like, ‘This is not it,’” he said. “I’m not young; don’t have a gym bod; it seemed like hookup culture, and I’m not into that.”

Mr. Buckalew is searching for an emotional connection, he said but has yet to find anything like the bond he had with his wife on the six dates he has had thus far. And as a single parent with expenses that include a car, house, and daycare, the additional costs of a babysitter and dinner dates can get expensive, he added.

“I’m just sort of giving up on trying to date I guess, for now,” Mr. Buckalew said.

For Ms. Harris, the Washington consultant, things have started looking up: While attending a networking event in November 2022, she initially didn’t think much of the 45-year-old man who she struck up a conversation with. She agreed to meet again platonically to discuss business over coffee. Instead, they talked for hours about everything.

“I actually met the love of my life,” said Ms. Harris, who has been in a relationship with her current partner, Ed, for about a year. “And it’s been amazing. Like, it literally has renewed my faith and hope and love. And that is possible at any age.”