Dating in the Middle Ages

Hudson Valley residents share their tales

Posted: Thursday, January 20, 2011

Dating. It’s not easy at any stage, but for baby boomers who may be giving love a second or third go round, it’s more of a challenge. The generation that began the free love revolution in the 60’s, has found many of its own divorced by the 90’s. Now they’re back in the dating game. In fact, according to a Time article from November 2010, “At, the 50-to-65 age group is the online dating site’s fastest-growing demographic, up 89% in the last five years.” Here are stories from some who know the trials and tribulations of boomer dating.

Felice Feinberg is on the HV Life sales staff. The 50-something from Washingtonville dreads dating. “I hate having to tell my life story,” she says. Married for twenty years, Felice went through a divorce and suddenly found herself dating again. “Dating is harder now than when I was in my twenties,” says Felice. “Back then I was thinner, cuter (writer’s edit: that’s her opinion!), and had a lot more options.”

Felice found that some men she met online were picky and arrogant. “I went out with a few guys from, but they just fizzled out. One guy said he had a great time after dinner, and would call again. He never did. Then a few weeks later, he contacted me again, like he didn’t remember me and said, ‘We should go out.’ It’s like, ‘You have to be kidding me!’”

Roanne Patterson, 62, is another sales staffer who has her share of dating stories. Her overall outlook on the dating scene goes up and down. “I go through stages. Sometimes I am all atwitter to do the online scene. Soon after, the enthusiasm wanes. Then every so often, I get the bug to dabble, and I have some fun again.” Roanne has used online dating in the past, but found it to be too much work. Felice agrees. “Who has time to fill out a 35 page survey?” says Felice. “Not me.”

Vincent, 52 from Washingtonville, says the same, “I never used dating websites, but I did go on to investigate the women on there, then suddenly you have 18 pages of questions to go through. I do want to try the sites eventually, but I have to sit down and actually do it.”

Both Felice, Roanne, and Vincent said they prefer to be set up by friends, rather than go the digital dating route. They feel their friends understand them better than a dating service. “However, there was this one date that my friend set me up on,” jokes Felice, “We won’t talk about that one.”

One Hudson Valley Boomer who has had success using online dating is Hugh Ford. Hugh is a 50-year-old who will not be single for much longer. It took a while for him to find Ms. Right and interestedly enough, she lives “across the pond.” Since his divorce three years ago, Hugh met women through friends and at local bars. While he liked some of his dates well enough, he says there was never any real chemistry. He had been out of the dating scene for so long, that he had begun to find things difficult. “It was tough as can be to actively go out looking for a date, let alone a partner,” says Hugh. Then, he looked online.

“One woman I met told me about a dating site called, ‘I Love Your Accent,’ a site aimed at Brits and Americans to get together. I gave it a try. That is how I found Gill. We connected in such a short time, that when she told me she was going on vacation in Florida, I threw caution to the wind and went to meet her.”

Sparks flew. She came here to visit Hugh a few months later and the two fell in love. Hugh proposed at the Tavern in Highlands Country Club in Garrison. “If you had ever told me that I would find love on a dating site I would have said you were crazy, but here I am ready to get married again and move overseas. I know it may not work for everyone, but after a couple of years of being single and finding no one compatible why not try something new?”

Another boomer dating story comes from HV Life’s art director, Leslie Cortes. She has gone down a different route to find the love of her life. The 48-year-old never thought a cab ride would lead to love, but that’s just what happened. Ironically back in 2009, she wasn’t shopping for a man. She had grown discouraged about the dating scene. She called a cab because she wanted to get some Christmas shopping done. “I was pretty turned off about men by then,” she says. The ride started innocently enough. She had a simple conversation with the friendly driver named Johnny, but soon the conversation grew flirtatious. By the end of end of the ride, she and Johnny Fraioli exchanged numbers. They’ve been inseparable ever since.

Leslie’s road to love has had some twists and turns. She tried online dating a few times. Although she enjoyed a few dates, nothing stuck. When she met Johnny, she just knew. “We are soul mates,” she says. Now she and Johnny are celebrating their first year anniversary with an engagement. “Five days after our anniversary, Johnny got down on one knee and proposed to me!” she says beaming.

One point that all the boomers want to make is that they truly enjoy dating, even though at times it can be difficult. Even Leslie and Johnny keep their relationship fresh by having date nights. “I am open to love. I go out with men and can enjoy their company without stress. If love happens, that’s wonderful,” Roanne says. Whether you have embraced the online dating scene or find dates through friends, go out and enjoy the activities that the Hudson Valley has to offer—and let things occur naturally. Don’t overlook those cab drivers either.

Meet up

If you aren’t ready to try an online dating site yet, then try! Meetup helps people with shared interests plan meetings and form offline clubs in local communities around the world. Very informal, inexpensive, and a lot of fun!

  • Hudson Valley Adult Play Group. They go to dances, dinner, movies, hikes, plays, whatever strikes one of your fancy. So if you are like-minded, this group is worth a glance.
  • Hudson Valley 30+ Mingles Singles. This group was created to help connect the over 30 plus crowd get together, make new friends, find romance, or just give you a reason to get out of the house and have some fun.


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