'Unlikely' In Love: Why I'm Urging My Friend Anne To Go For Online Dating

My friend Anne just turned 60, and she looks great. She has a great job, the capstone to a great career. She has two kids she adores and two ex-husbands she doesn't. She is full of energy and curiosity and has tons of friends. But no "boyfriend" (to resurrect a term from the past) to do things with, to have sex with (or not), to laugh with, but not necessarily to get serious with (though that would be nice).

She nags her friends to find someone for her, but so far she has not been fixed up once. I used to wrack my brain looking for someone suitable (I happen to think a younger, less powerful guy would be ideal) but now I am wracking my brain for ways to persuade her to try an online dating service. For one thing, it would expand the universe of contacts beyond the six degrees of separation we live in. For another, the Anne we are looking to match up with someone suitable is limited by history -- who she has been, not who she can still become.

Having written a book about the subject (How We Love Now: Women Talk About Intimacy After Fifty). I hear story after story about serendipity, rekindled romance, and true love -- all found on the Internet. Not to mention the queen of domesticity Martha Stewart and novelist Joyce Maynard, two recent success stories. I know of a 25-year-old rebel who found a woman as tattooed as he was, a 35-year-old who posted the statement "I don't want to mess around; I am looking to get married" and met the love of her life (a millionaire, no less) and I know numerous women Anne's age who have met "unlikely" matches who have turned out to be terrific dates.

"Unlikely" is the operative word here. We all have made mistakes in our romantic lives, and some of us have made a habit of "bad choices." (As one woman told me, "I keep getting involved with the same guy -- just a different penis.") If the computer does the choosing the chances are much better that you will be presented with someone who fits with your best qualities and real needs rather than your hang-ups and unrealistic expectations. Moreover, many women my age can't shed the old mantra that he needs to be richer, more successful, taller, and simply heroic -- until they meet someone younger, poorer, less educated, less powerful who adores them. Someone "unlikely."

If I am going to persuade Anne to look for love in cyberspace, I have to answer her biggest objection -- that she is so inexperienced in present-day mores that she wouldn't even know how to evaluate candidates. So I turned to the expert in love, sex, and marriage who has studied and advised our generation since back in the seventies when she wrote about egalitarian sex and "peer marriage" for us at Ms. magazine. Dr. Pepper Schwartz is now the "Love and Relationships Ambassador" for AARP and has worked on developing algorithms for the dating site PerfectMatch.com. Her latest book (with Chrisanna Northrup and James Witte) is called The Normal Bar: The Surprising Secrets of Extremely Happy Couples and her next, Dating After 50 for Dummies, will be published in December, 2013.

Who better to demystify the process for novices like Anne? You won't learn much from answers to specific questions, she says, because "usually you can't see exactly the way they answered questions in the matching algorithms;" you need to pick up on patterns. Her recommendations were echoed by some old hands at the game whose comments (in quotes) are included. Here are some of the characters to avoid:

Someone who talks about how much you will enjoy sharing their life and doesn't mention that they would like to share yours.

...who falls in love with you within a couple of emails (usually a scammer). ("This person is going to be a pain; they don't know anything about you and they don't know anything about love.")

...who says they are fit and you better be too (the first part without the second is ok). ("Unless you are obsessed with your body too. Superficial folks deserve each other.")

...who won't look at a relationship that isn't within fifteen minutes of her or his own place. ("Why bother?")

...who says that they are not looking for a committed relationship (believe them, they aren't telling you the half of it). ("Unless, of course, you aren't either.")

...who has too long a list of particulars that you have to fit; a long list of deal breakers and "must haves" is the sign of a narcissist - or at the very least someone high maintenance. ("Tell me about it!")

...who wants people who are far younger than they are - and people who are particularly proud of "how young they look." (People do look younger these days, but for some it is just a code word for having prejudices about people their own age).

... who sounds angry or resentful when they tell their life story or complains about disappointments they have had on line. ("Unless it's humorous. Humor counts for a lot.")

...who list all their toys and their houses or financials as the biggest part of their sales job.

And my personal favorite: Someone who doesn't take the time to proof-read what they wrote ("the difference, for example, between there, their, and they're").

Now, Anne is pretty savvy and should be able to pick up on most of these warning signs on her own, but women like us often second guess our gut responses, especially when it comes to entering an intimate relationship (friendships as well as romance). "I'm being too picky" "Not my type" "Everybody is self-involved" "Nobody's perfect; I'm certainly not!" With the computer as intermediary, Anne has a real opportunity to take risks, make demands, be choosy, present herself as she knows herself and look for new -- and "unlikely" -- frontiers of intimacy for her Second Adulthood. Furthermore, her friends and family will never know what she is up to. As Julia Child famously said when she picked up a glob of potatoes she had dropped on the floor and returned it to the pan, "Who is going to see?"

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