Romantic love can be associated with youthbut what happens to those of us who find ourselves looking for them in our fifth and sixth and more decades? A friend of mine (married) says that what scares her most in being single now would be to undress in front of a new man. "At this point," she says resignedly, "I only have the ambition to look beautiful with clothes."
But when Data Lab sent me the profile of a 63-year-old retire named Willie Best, along with a selection of potential dates of similar ages, I was excited by the challenge of "fall" matchmaking.
Willie is a handsome and fit former city manager who seemed open to new desires and adventures. I partnered with Carolyn Conyers, a dynamic 60-year-old political consultant for the federal government that runs a small jewelry business on the side. As her profile has noted, Carolyn is typically mistaken for a woman 20 years younger. He presented photos of herself in clothes wrapped in a figure with her arms toned. Carolyn said he was looking for a man "at ease in his skin, financially affirmed, adventurous, and not bad for the eyes."
Both she and Willie have already been married and have raised children (two daughters in the case of Willie, four in Carolyn and 12 grandchildren). I could only foresee a negative potential for each one. Willie lives in Chapel Hill, northern California, so at first glance, we're looking at a distance relationship. (He insisted that driving a few hours was not a problem.) Meanwhile, Carolyn had been married four times – which could scare off a potential suitor looking for a job.
We sent them to Chart House, a famous fish restaurant in Alexandria overlooking the Potomac. It was a warm October evening. Carolyn arrived first and waited outside. Willie arrived 15 minutes late in his Mercedes SUV.
"She was attractive, in a red dress, natural short hair in dreadlocks, she looked fit," Willie said.
Carolyn, accustomed to the attentions of the younger ones, was taken aback by Willie's aged appearance. But she told me she was determined to keep an open mind.
The two entered 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 does not drink. In fact, he rarely drinks, he explained later, but he needed something to relax him. Carolyn does not drink alcohol.
Despite the initial hesitations of Carolyn, the couple had so much to say that the date was reversed downstairs after dinner at the bar, where the two have practically closed the place. "We talked about life, marriage, her children and children, her grandchildren," Willie said.
Carolyn agreed that they had a "good conversation", but said she was thrown when she learned that she lived in North Carolina. "When you need a hug at the end of the day," he said, "that person will not be there".
When I asked Willie if there was anything that bothered him about Carolyn, the fact of his multiple marriages came up immediately, followed by his declaration, during dinner, that he would have liked to marry again. "I'm more conservative and southern, my parents have been married for 50. I never expected to be divorced," he said. But he did not raise his concerns about marriages with her. "It's none of my business," he said.
In the end, however, it was not the distance or conjugal history of Carolyn that was the insurmountable problem. It was Willie's concern for his ex-wife from his second marriage, which ended six years ago. After leaving their marriage, they continued to meet each other from time to time and talk on the phone twice a day until a few months ago, when they admitted to having remarried in 2015. "I was hoping we could get back together," Willie allowed.
"I do not even know why he's coming out right now," Carolyn remarked. "You can not have a relationship when you try this kind of heartbreak."
Since Carolyn ended her last major report in 2004, she says it's "ok to be single". It is not a philosophy that felt that Willie was ready to share, though.
After leaving the restaurant, Willie left Carolyn to his car. Contact information has been exchanged but nothing else. "All right," said Carolyn. "I hope Willie gets to where it must be, she's a good person."
Rate the date
Willie: 4 [out of 5].
Some messages, but no second appointment.
Danielle Crittenden is co-host and executive producer of the "Femsplainers" podcast on the Entertainment One network.