Adventures in online dating

Mature Vineyard singles talk about finding love on the Internet.

Illustration by Kate Feiffer

Updated: 2/14

Years ago, my stepmother, who was then in her 70s, was planning to come over to our house from Falmouth for Thanksgiving dinner, and she called the day before to ask if it would be all right if she brought a friend — someone she had just met on We said of course, and then looked on in bemusement as she made out with her friend in front of the fireplace after dinner. 

If I had any questions about how mature singles, let’s say singles over 50, were adapting to dating in the digital age, at least based on my stepmother, they were doing just fine. Back in the day people met the old-fashioned way … through friends, at work, or in bars. But I wondered how seniors, in the age of, Tinder, and Bumble, were adapting to making matches.

I started by asking a contributing writer for The Times, Abby Remer, if she had any experiences with online dating. Abby is a youthful 60 years old, blond and attractive. She is from New York and was divorced in 2000, and while she was leery of online dating, she decided to give it a try. “When you first go online, you get inundated,” Abby said, “you’re juggling emails, looking at profiles — it’s like a whole other job.”

Abby decided to set some guidelines. “First of all, people had to have photographs,” she said; “I wouldn’t even answer anyone who didn’t have a picture.” Abby would ask men what they were curious about, what gets them up in the morning. She was looking for dates who were thoughtful. If she was sufficiently interested, things could progress to a cup of coffee. But having set up the guidelines didn’t necessarily ensure a good coffee date. 

There was the guy who tried to deep-throat kiss her at the end of their coffee date. There were the guys who misrepresented themselves with old pictures, there were the guys who turned out to be married. Abby ended up dating a few guys, but nothing serious came of it.

When Abby moved to the Vineyard about three years ago, she resisted online dating until three months ago. When I talked to her, she had just quit The first coffee date she had, the guy talked 45 minutes straight; she couldn’t even interrupt long enough to say she was leaving.

The next guy walked in, looked Abby up and down, and said the magic words that send a girl’s heart aflutter: “Nice package.” 

While Abby’s experience in online dating left a lot to be desired, for others it turned out to be a match made in heaven. People like Sally and Bob, as we’ll call them. 

Both Sally and Bob are professional people in their early 60s. Sally, who lives in Vineyard Haven, had been divorced for many years, and was encouraged to give online dating a chance by her friends — they sat around drinking wine one night, and helped her make a profile on

Sally ended up having one date from her posting, a guy in Wareham. “Nice guy,” Sally said, “but it didn’t go anywhere.” But then lightning struck. Sally said she struck up a correspondence with someone named Bob on the North Shore. “He had a nice face,” Sally said, “and it looked like we had a lot of interests in common.” Plus, one of the pictures he posted looked like it was taken at one of Sally’s favorite spots, a house off South Beach. 

Bob confirmed that in fact it was the same house, and, like Sally, he said it was one of his favorite places in the world. Long story short, Bob met Sally for a date, and from the minute they looked at each other, they knew it was the real thing. They were married at “their favorite place” two years ago. ”I’m proud that we met online,” Sally said. “I wasn’t really looking that hard, and kind of thought I might never meet someone again; our story should give other people hope.”

A gentleman we’ll call Nelson of West Tisbury is 77 years old; his wife of many years died in 2016. He wanted to be with the grief for a while, but after six months, he decided he would like some companionship. Dating websites appeal to a wide range of interests, and Nelson’s interest in the environment led him to join, an eco-conscious site, and a spiritual site called Conscious Singles.

The first woman he met had said that if you were over 70, don’t bother to respond. Nelson was 74 at the time, but he convinced her to give it a try, only to find out she had lied about her age. Lying about one’s age is quite common online. Nelson drove out to meet a woman in Gloucester who upon meeting him confessed that she had lied about her age — by about 15 years. She said she was in her late 60s, but actually she was in her early 80s. 

In the course of his online experience, Nelson met around 20 women. Some relationships lasted over a year, most were one and done. Nelson said that a lot of the women had been dumped by their husbands, and were financially insecure. In his profile he suggested that he was a financially stable 70something-year-old-man, which tended to attract some gold diggers. They were easy to spot. Nelson said, “Why would women in their 20s and 30s otherwise be interested in a man in his 70s?”

Nelson’s online dating days were over when he met Natalie, a woman from the Midwest. “Initially she was only interested in being a pen pal,” Nelson said, “but I convinced her to meet me in Florida, and we talked for four days and nights.” Natalie moved in with Nelson last year.

Let’s call our next online dater Joanne from Oak Bluffs. Joanne is an attractive, energetic, and outgoing woman in her 60s who was divorced in 2000. She said there’s kind of a stagnant single population on the Island, so she decided to give online dating a try. 

She joined eharmony for a year, and admitted to being very picky. The site recommended 30 people to her, but she didn’t engage with any of them. Then just as her subscription was about to expire, she saw someone who looked promising: David, a coach and teacher in New York. She showed his profile to her friends, and they all said, “Go for it.”

Curiously, David didn’t want to talk on the phone; he didn’t want to be biased by someone’s speaking voice, so they decided to meet in person. It was a nice match, and they began seeing each other for several years. “It was like feast or famine,” Joanne said, “we went from seeing each other about once every six weeks to having him move in with me for the summer.” David got along well with Joanne’s two children, but they broke up soon after David went home at the end of the summer. Ultimately the problem was that Joanne was going through a lot of trauma in her personal family life, and she just didn’t think it was fair to drag someone else into it. 

Joanne misses the laughter, conversation, company, and physical contact of a man, and would consider online dating again. ”But for now,” she says, “I’d take a dog over a man. They’re loyal, loving, consistent, predictable, low-maintenance, and easy to feed.”

After her divorce, a woman now in her 60s whom we’ll call Missy soon realized there was a very small pool of eligible men on the Island. In the ’90s, before the widespread popularity of dating websites, Missy tried her hand at speed dating. One winter a speed dating event was held at the Outerland night club. Like musical chairs, everyone would take turns circulating around the room, and get three minutes to talk with one another. “The only problem,” Missy said, “was that I was a former teacher on the Island, and I kept getting matched up with my former students. I was old enough to be their mother.” 

When she was in her 50s, Missy gave online dating a try, and without much better luck. “I’m old school,” Missy said. “I think you just need to meet people in person. Having said that, I actually met someone from a website called Plenty of Fish, and it was a disaster. I went off-Island to meet this guy,” Missy said, “and it turns out he lived at home with his mother and 20-year-old kids — there was so much dysfunction!” 

Deb, as we’ll call her, is in her late 50s, and is affable and outgoing. She was married for 20 years, and after her divorce she tried online dating for a while with no success, although she developed several friendships. A friend of hers told her, “Don’t stay single too long, or you’ll never get married.” Several people we talked with agreed with this advice; the longer you stay single, the more autonomous you become, and the more you value your independence. 

Deb hasn’t tried online dating for some time, although she said that she works at the hospital, and much of her social life comes from people she meets at her job. “If I quit my job,” she said, “I might have to go back online.”
Jib Ellis is a writer from Oak Bluffs in his 70s. He was married for 20 years, and was devastated by his divorce. He gave online dating a try when he was in his 60s. All in all, Ellis said, many of the women he corresponded with had faced an ugly divorce, and he was struck with “the resounding echo of their loneliness.” 

He did go on one date, which wasn’t that successful. “We had to take separate cars,” Ellis said, “because she didn’t want me smoking in her car.”

So let’s end on an upbeat note. 

Tricia Bennett of Chilmark is a therapist, and when she was in her late 40s, just three days before her membership in was about to expire, she got a message from her future husband, Richard. They began dating, and after three years they were married at that quintessential Vineyard setting, the raw bar at Larsen’s Fish Market in Menemsha. 

Tricia has written a book that is soon to be published, titled, “Finding True Love: Authenticity and Joy at any Age,” and in it she has advice for senior online daters. Rule No. 1 is: Authenticity is the key. Don’t misrepresent yourself. Which of course is good advice both online and off.
In her book, Tricia writes, “My husband and I thought that the Internet was the last place on earth that we would ever meet our partners, but through the urging of friends, we tried it. Lo and behold, we met online at 47 and 60 years of age! Fifteen years later, we still comment on how lucky we are to have found each other. I could not recommend it more highly.”

‘Fiascos and Fun’: Share your online dating story, or simply listen to others. Tricia Bennett, author of soon-to-be-published “Finding True Love, Authenticity, and Joy at Any Age,” will be at the Vineyard Haven library on Feb. 23 from 2 to 4 pm, with hints about your online search for companionship. All ages welcome; refreshments will be served.