Listen to the first two chapters of Daring to Date Again: A  Memoir here!

When a 60-year-old woman starts to date again, she won’t be invited to the prom or go through the stages she expected as a girl – going steady, being pinned, engaged, married, and finally widowed and alone. She is financially stable and professionally credentialed. She is a matriarch, a pillar of her church, a member of a choir, knows her neighbors, helps out at the food pantry. She has a lot at stake.

For this 60-year-old twice divorced woman marriage had lost its sheen. My needs had been whittled down to conversation and sex. I could get conversation from my friends or colleagues; finding sex was a riskier matter. The term “friends with benefits” sounded juvenile. “Having an affair” sounded illicit. “Getting married” sounded terrifying. “Romp in the hay” was more like it, with a nice, quiet conversation before and after.

What I knew of love was shrouded in rules and expectations soon to crumble under the weight of new experience. The anonymous Internet would make it safe for men (and me) to reveal thoughts and wishes that had long lain unearthed. Distance would shrink to a simple click. And I would commune with hundreds of men.

Like a gay teenager, I had believed my thoughts and desires were not shared by others. A little door opened when a relative told me that widowed Great Aunt Tony, who died in 1982, had not been the begirdled figure sitting in a straight chair that I remembered. “She had some kind of romance with Grant Cushman. He used to live out on Longacre Road. I don’t know exactly what happened there.” It comforted me that I was not alone as I stepped into a world where I felt I was risking everything.


At the Rope’s End

On a hot September afternoon in 2003 I left the rest of the picnickers and walked to the secluded nude beach where a hundred or so naked people were casually fishing, swimming, and talking.  I took off my clothes, folded them on the towel, weighted them down with a stone, and eased into the cool water of a Vermont lake.

As I swam, my shoulders moved freely without restraining straps.  Without a bathing suit, the temperature of my tummy was the same as my back, my legs.  The water streamed against my body like a caress. I swam and swam, then lay on my towel to dry off in the enveloping sun.

I had come to a weekend at the Rowe Camp and Conference Center to find someone to have sex with. I might have said “companionship” or some other euphemism, but really, it was for sex. Twelve years of celibacy had become intolerable. I was turning off the lights in my living room and dancing wildly alone; I avoided romantic movies because they upset me so; my sleep was disturbed by erotic dreams. My kindling body burst into flame at the slightest frisson of affection. I was even ambushed by an orgasm while lying stock still on my bed thinking about a man I had become obsessed with. I didn’t know that was possible. I was afraid that my anguished body would force me to do something stupid, and I had already done enough stupid things in my life.

I would have to sacrifice the delicious liberty of celibacy and find a man to have sex with. My cousin had given me memberships to Rowe for two years, saying I should go there, the people were nice. Here I was. Maybe that man was here too.

I was dubious about finding a lover. Every bit of instruction or advice I’d ever received about sex was nonsense, but I wasn’t sure what the truth was. When I was growing up, my mother told me, “Men are animals,” so I had always viewed men with caution. They could do you some real damage if you got pregnant, and could suck you dry. But wasn’t I an animal too?  The more I resisted sex, the more animal-ly I became. My father said, “Men like fast women, but they don’t marry them.”  For a girl growing up in the 1950’s, marriage was all there was. Without it, I’d be a librarian or teacher, dessicated, cut off from society. The world marched in pairs, and I wouldn’t have anyone to go to the movies with except another spinster, another old maid.

My second husband threw in a warning when we divorced, “There’s no more chance than a snowball in hell that a woman over 40 will ever marry again.” Yes, men preferred younger women – everybody knew that, and I was almost 50 when we divorced. Life without another marriage was better than life with my second husband, but life isn’t all-or-nothing, either-or. Given my skittish pessimism, I wasn’t surprised that my celibacy had gone unchallenged by the slightest interest from a man.  But unless I wanted to dance alone in my dark living room for the rest of my life, I would have to seek the touch of a man. I would have to seek it.

After my beautiful swim, I walked back to the picnic ground and screwed up the courage to tell a retired nuclear physicist, Roger, that I had never ridden on a motorcycle, and asked him to take me back to the farmhouse on his. He seemed happy to do it, and I climbed up, wrapped my arms around him, and relaxed into the tight embrace.

Over dinner that evening, I chatted with Lenny, a curly-haired, divorced carpenter specializing in historic renovation.  He had a kind, quirky manner and an interesting fashion sense – black velvet jacket, bright pink shirt.

After dinner, we folded up the tables in the dining hall and a local band played rock and roll.  People who couldn’t dance worth a damn were welcome on the floor, their out-of-sync bodies showing the same joy as everyone else’s. In one day, I had flirted with two different men, and that made me giddy. The future was looking bright, I was wearing the Red Shoes, dancing alone, only this time in public.

On a break, I faintly saw the shadowy outline of someone looking in from the dark deck outside the dining hall.  I was struck by this person’s hesitation. Moments later, Lenny came in wearing fishnet stockings and heels, a scarlet bow around his waist, a flouncy black skirt and corset top. He had a large red bow in his curly hair.

He came straight over to me and grabbed my hand, pulling me onto the dance floor. His cheeks had rounds of bright rouge which made his lipstick seem more scarlet. He had powdered over his whiskers, and his long eyelashes were coated with mascara.

I was wearing sneakers, blue jeans, and a plaid lumberjack’s shirt and felt ridiculous, but he was glowing, so I said, “You look beautiful, Lenny.”

“Thank you!  Thank you!  I feel beautiful. This is the first time in my life that I have ever gone out in public dressed like this, and I feel wonderful!  Do you believe that?  The first time.”

I was humbled and flattered that I was the first woman he had danced with as his natural self.  He had been coming to Rowe for years, gotten comfortable there, and had chosen this night to emerge from heaven knows what misery. I didn’t have the heart to put him off, though my instincts were objecting loudly.

He pulled me close, his rouged cheek against mine. I chattered and laughed to cover my discomfort. Was he gay and just having dressup fun, or was he a heterosexual transvestite who was making a pass at me? It seemed the latter.

Yes, here he was! A man who wanted to have sex with me! But I just couldn’t soften my body against his satin self. When the dance was over, he put his forehead on mine, and I squeezed his hands and said, “That was great,” and went off to get a glass of water. I just couldn’t do any more.

Seeing how much I love silk, and how much other women love lace, satin, and jewels of a refined kind, it seemed churlish to deny Lenny the pleasure of wearing them too. Too bad that men in lipstick made me uncomfortable in some place which was not governed by my mind.

I was disappointed that the first man who had asked me to dance in twelve years was wearing a skirt, but it felt wonderful to dance with any man again.


No miracles happened during my weekend at Rowe – or maybe they did. A little stone moved inside me and opened my way forward.

Back at work, Keith, a husky, blue-eyed, ukelele-playing paralegal, began to drift by my desk daily.  He was ten years younger than I, so it never occurred to me that he might want me.

Keith was brilliant – he could remember baseball statistics, play songs vivace on the ukulele, recite poetry, add up numbers in his head, read text in a mirror, and quote famous philosophers. Being a secretary was boring, and he brought some levity and variety to my days. But there was a tide of anger in him, and a vulgar side, and I didn’t want to be alone with him, not even for lunch.

One day he sent me an email:  Pardon my venturing a terribly porcine, lascivious and salacious affirmation. I think you’re hot, irrespective of your age. oink. oink. So he really was strange, the man who liked older women, the loner caught up in a sick fantasy.

He was such an interesting mix of the Good and the Awful that I was tempted to take him up on his offer of a baseball game, or a little ice skating in the park, but then he would poke the index finger of one hand through a circle made of the thumb and first finger of the other hand, or display his tongue, and my fragile fantasy would collapse. I would have to look further.