Getting Back Into It

John Connor's 33-year marriage took him away from the dating scene for a long time. But after his wife Diane died in 1997, the software-company executive and father of three grown children found himself alone and lonely for the first time since his 20s. As he worked at his computer one day in 1999, an ad popped up on the screen for a free trial membership on Match.com one of the nation's largest matchmaking websites. Looking for a female companion who would share his interest in health and physical fitness to go out to dinner and movies with and not having met anyone he liked at local church functions Connor decided to place his profile and photo on the website. Through Match.com he wound up meeting a divorce, Barbara Errickson, 58, who also worked in computers. Even though marriage was the last thing on their minds, they hit it off immediately and were eventually wed two years ago.

"The Internet gave me a new way to meet and date at this stage of my life," says Connor, 60, who divides his time between homes in Plano, Texas, and Naples, Fla. "It's making that initial effort when you find yourself alone after so many years with one person that's the hardest part of dating."

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More and more baby boomers like Connor single again after being widowed or divorced are trying new-wave methods of dating such as cybermatchmaking, methods that could only have been deemed science fiction 30 years ago. In fact, at Match.com , one of an estimated 2,000 singles websites, about 360,000 members who have posted profiles are 50 or older, says Trish McDermott, its resident dating coach. That is 10% of the site's total profiles. Other newly unattached baby boomers are writing personal ads, dating in groups and still using such tried-and-true methods as the fix-up from well-meaning friends.

"Dating as you get older is both easier and harder these days," says noted psychologist Dr. Joyce Brothers, author of the 1990 book Widowed: How to Cope with Loss. "It's more acceptable to date at this stage in life, but you may find fewer people that you really like in your age group."

The old rule about waiting a certain number of years before dating again, especially after losing a spouse, is disappearing. Many boomers now find even their grown children encouraging them to look for romance by a variety of means.

"In some ways, it's easier for people in their 50s and 60s than for those in their 20s and 30s to date, since they have been in a committed relationship before and know what is involved when it comes to marriage," says Houston psychotherapist Sarna Sunshine. "They're also now finding that society has fewer taboos these days about sex and older couples, even if they are dating after having been in a long marriage."

One taboo that has been relaxed is the one against an older woman with a younger man. Twice-divorced Sally Salners, 54, a Houston interior designer, says she receives support and encouragement from friends and family for her two-year relationship with her 33-year-old boyfriend, a sales consultant. They got to know each other when Salners helped him decorate his apartment.

"Sure, we've had people in a store or restaurant mistakenly think I was his mother," says Salners, a grandmother whose eldest daughter is the same age as her boyfriend. "At first I was hypersensitive about this, but now we both just laugh when it happens."

New Yorkers willing to try something new and different in the world of dating can head over to the Drip Cafe in Manhattan, grab a cup of coffee and a muffin and get fixed up for a date. Drip patrons scan anonymous written profiles of other singles, indicate which ones sound interesting and, if both parties agree, have a Drip staff member arrange a date for them, according to Nancy Slotnick, the cafe's founder and chief executive officer. Each couple has its first date at the coffee bar, with a Drip waiter or waitress making the introductions. There are 10 other affiliated cafes in New York, New Jersey and Connecticut and two in Boston. The chain plans to expand to Chicago, Los Angeles, Miami and Washington, Slotnick says. In addition, Drip.com offers matchmaking services via the Internet.

"I went to Drip because it sounded like a gas, something different to do," says widowed kindergarten teacher Jaki Williams Florsheim, 58. She had her first date with divorced accountant Henry Florsheim, 54, at the cafe in 1999. She had asked to meet him after reading his profile. They were married a year later and now live in Brooklyn, N.Y. "If you had told me that I would meet my husband through a place like Drip," she says, "I would have said you had to be kidding."

But while there may be more ways for boomers to hook up these days than there were years ago, many of them still find it painful even to contemplate dating after being with one person for decades, as Brothers points out. This is especially true of those who are newly widowed versus those who are divorced and may have been looking to leave their marriage for a while. "No matter what you do," says Martha Parry, 65, a widow and retired insurance-agency owner in Oakdale, N.Y., "it's hard to get used to anyone else after being married for 36 years."