Romantic love may be associated with youth, but what happens to those of us who find ourselves searching for it in our fifth and sixth-plus decades? A (married) female friend of mine says what would scare her most about being single now would be undressing in front of a new man. "At this point," she explains resignedly, "I just aspire to look good in clothes."

But when Date Lab sent me the profile of a 63-year-old retiree named Willie Best, along with a selection of similarly aged potential dates, I was excited by the challenge of “autumn” matchmaking.

Willie is a handsome, fit former city manager, who seemed open to new desires and adventures. I matched him with Carolyn Conyers, a dynamic 60-year-old policy adviser for the federal government who runs a small jewelry business on the side. As her profile noted, Carolyn is typically mistaken for a woman 20 years younger. She submitted photos of herself in figure-hugging outfits with toned bare arms. Carolyn said she was looking for a man “comfortable in his skin, financially established, adventurous; and not bad on the eyes.”

Both she and Willie have been married before and have grown children (two daughters in Willie’s case; four in Carolyn’s, as well as 12 grandchildren). I could foresee only one potential negative for each. Willie lives in Chapel Hill, N.C., so right off the bat we’re looking at a long-distance relationship. (He insisted that driving a few hours was not a problem.) Meanwhile, Carolyn had been married four times — which might scare away a potential suitor looking for commitment.

We sent them to Chart House, a popular seafood restaurant in Alexandria overlooking the Potomac. It was a warm October evening. Carolyn arrived first and waited outside. Willie pulled up 15 minutes late in his Mercedes SUV.

First impressions?

“She was attractive. In a red dress. Short natural hair in dreads. She looked fit,” Willie said.

Carolyn, accustomed to the attentions of younger men, was taken aback by Willie’s aged appearance. But she told me she was determined to keep an open mind.

The two went inside and took a table upstairs where it was quieter. Both ordered the shrimp stuffed with crabmeat. Willie ordered a gin and tonic, something he usually doesn’t drink. In fact he rarely drinks, he explained afterward, but he needed something to relax him. Carolyn doesn’t drink alcohol.

Despite Carolyn’s initial hesitations, the couple had so much to talk about that the date spilled downstairs after dinner to the bar, where the two basically closed the joint. “We talked about life, marriage, her kids and my kids, her grandchildren,” Willie said.

Carolyn agreed they’d had a “nice conversation” but said she was thrown when she learned he lived in North Carolina. “When you need a hug at the end of the day,” she said, “that person’s just not going to be there.”

When I asked Willie if there was anything that bothered him about Carolyn, the fact of her multiple marriages immediately came up, followed by her statement, over dinner, that she’d like to marry again. “I’m more of a conservative, Southern kind of guy. My parents have been married 50 years. I never expected to be divorced,” he said. But he didn’t raise his concerns about the marriages with her. “Not my business,” he said.

In the end, however, it wasn’t distance or Carolyn’s marital history that was the insurmountable problem. It was Willie’s preoccupation with his ex-wife from his second marriage, which ended six years ago. After she walked out of their marriage, they continued to meet up occasionally, and talk as often as twice a day on the phone until a few months ago, when she admitted that she’d remarried in 2015. “I’d hoped we might get back together,” Willie allowed.

“I don’t even know why he’s dating right now,” observed Carolyn. “You can’t have a relationship when you are experiencing that kind of heartbreak.”

Since Carolyn ended her last major relationship in 2004, she says she’s “okay with being single.” That’s not a philosophy she felt Willie was ready to share, though.

After they left the restaurant, Willie dropped Carolyn at her car. Contact information was exchanged but nothing else. “That’s okay,” Carolyn said. “I hope Willie gets to where he needs to be. He’s a nice person.”

Rate the date

Willie: 4 [out of 5].

Carolyn: 3.


Some texting, but no second date.

Danielle Crittenden is the co-host and executive producer of the “Femsplainers” podcast on the Entertainment One network.