When You Start to Date Again, Find Someone to Talk About It With

Starting to date at sixty, after two divorces, might prove humiliating or catastrophic. If I failed, which I would certainly do, over and over, I wanted to do it privately, but not necessarily alone.

Unless I changed myself, the odds were that I would end up struggling through another unfulfilling relationship. I would have to challenge myself by dating men who were not like the men I had known before—slippery ground. Considering the unsettling experiences I would have, I would benefit from having a confidante. My best friend wasn’t completely in the dark. I shared with her the generalities about budding and fading relationships, or funny stories about the man who wore only white, the judge who assured me that the American and Chinese governments were both controlled by a group of men so secret that nobody knew who they were, or the doctor whose schedule only allowed for dates on one night a week. She never suspected the breadth of experience that the Internet was giving me, and I didn’t want to risk her disapproval by filling her in on what I had learned about masturbation, group sex, the traveling salesman whose wife left him when he gave her syphilis, or the more ordinary stories about men whose marriages had calcified and didn’t know what to do. My friend and her husband had once gone through a major kerfuffle over his indiscretions, and I didn’t want to sharpen her painful memories.

My close friends were used to the old me, and I was afraid that if I became too wild or controversial, they would drop me. Paying a therapist to listen to me would be too expensive.

The first people I confided in were the men I met anonymously on the Internet. Many of them were in the same boat as I was. We confessed our hopes and mulled over decisions together. How probable did one man think it was that another man who had just contacted me had actually served in inner CIA circles? Why was a boy of 18 writing to a woman of 60? What level of endearment was “babe?”

I had three years of conversation with a stay-at-home dad in Manhattan, just across the river from me. He was wise, experienced, married, and bored. We advised and supported each other through emails, but never met. A Liverpool correspondent had a different set of social expectations since he lived in England. Getting personal information out of German men was like unlocking a safe. These men helped me to change and entertained me, and I learned the value and limits of Internet friendship.

The discipline of not confiding in the people I would ordinarily have turned to forced me to go deeper into myself, which is exactly where I needed to go.

When I started dating online in 2003, there were no books or movies dealing with the dating dreams and habits of people over 60.  In 2004, A Round-Heeled Woman, My Late-Life Adventures in Sex and Romance, by Jane Juska, created a small sensation. Her blurb was “Before I turn 67—next March—I would like to have a lot of sex with a man I like.” By the time I was the cover girl on ELDR Magazine’s 2008 issue on Sex and Intimacy After 60, the subject was no longer taboo. Before Jane Juska, I was on my own.