Internet dating is the 21st century version of the blind date. It has replaced the hook-ups of the eighties, the bar scene of the seventies, the rock festivals of the sixties, and the mixers of the fifties, as the way men and women meet and get together. Statistics show that it’s the third most common way that relationships start in this country. What’s more, one in six new marriages now begin with an Internet connection, according to an article by Nick Paumgarten in the July 4th, 2011, issue of The New Yorker.

And who’s leading the digital dating pack? The New York Times reports that singles 55 and up “are visiting American dating sites more than any other age group.” As a clinical psychologist specializing in relationships and a professional dating coach, I know that many women over 40 are logging on in hopes of finding love. I also know that these women face a special set of issues when considering romance — whether widowed, divorced, or never married.

If you’re considering online dating, you’re likely familiar with at least one of these common obstacles:

Ambivalence, especially after divorce or break-up, is one of the most troubling, tricky, and ubiquitous issues that women face when they resume dating. Research shows that older women recover more slowly from break-ups and are more wary of starting new relationships than younger women. Many times, this is with more than good reason, as the ambivalence about starting over has been born of bitter experience. Their friends and children may urge them to get back in the game. (According to the Times report, children now buy Internet dating memberships for their parents, and vice versa!) But often much time, effort, and healing are required before the triumph of “hope over experience” can be achieved.

Lack of confidence often goes hand in hand with ambivalence, as nothing can shake one’s self-esteem as completely as the end of a relationship. Most women, particularly if they haven’t dated for awhile, feel insecure about “being on the market” at an older age. Unfortunately, the majority of us are acutely aware of our physical flaws at any age, and there are more of them to obsess over now. This feeds into another common difficulty: figuring out how to present oneself. Creating an interesting and accurate profile, choosing an alluring and flattering picture, attracting a like-minded man, and so forth, can be anxiety provoking and challenging to self-esteem.

Uncertainty about the new rules of dating. Much has changed about dating in the years (sometimes decades) that may have passed since an older woman has been “out there.” One issue that comes up often is the question of who picks up the check. As Nora Ephron once quipped, the only real achievement of the feminist revolution seems to be the Dutch treat, but I have known both women and men who have been offended when it is suggested that the bill be split. What does it mean? Just that he/she is modern? Or he’s cheap? He doesn’t like me? She doesn’t respect me, doesn’t want to see me again, she’s after a rich husband? In the old days, there were rules that dictated dating behavior and protected us from all these bewildering questions (at least at first). Now, this simple act requires the skills of a cryptographer!

Fears about sex. I am always reminded of the scene in the movie Sleepless in Seattle, in which Rob Reiner mentions tiramisu to Tom Hanks, who’s about to go on his first date since becoming a widower. Hanks thinks it’s a hip new sexual technique and begs Reiner to tell him about it. Few people are likely to mistake a dessert for a modern addition to the kama sutra, but for couples in their 40s, 50s, and beyond, sex can be a minefield. Consider all the changes in sexual mores that have taken place in the past few decades: First, sex was shameful; then, virginity was shameful; next, sex was dangerous. Menopause, illness, and aging create a new sexual landscape for both sexes, and although freedom from contraception is a plus, the dangers of infection persist. Fears and expectations can be especially difficult in this area, and both men and women feel more trepidation about being physically intimate with a new partner than when they were younger (as if it was always easy then!)

Getting duped, or hurt, or worse. Decoding men’s profiles, reading between the lines, recognizing red flags, while at the same time learning not to overlook the occasional “diamond in the rough” requires patience and, usually, a lot of sorting out. Everyone has (many) more misses than hits. Almost every man claims to be “athletic and fit,” and it’s very common for men (and women) to lie about their age, and worse. Women are especially fearful about being deluded, or, of course, romanced by someone dishonest or dangerous. As one woman said to me, relieved when she finally met a man she had been talking to online, “He seems to be who he says he is.” The man in question was that and more: a good match. Like her, he was widowed after a happy marriage, and though she’s still hesitant, so far they’re enjoying being together. It took a long time for her to overcome her fears and worries about dating in general and Internet dating in particular, and though nothing much has happened yet, she’s thanked me for helping her at least five times. To paraphrase E.M. Foster, it can be good to “only connect.”


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