Me and Anne Lamott, Dating Online

As I’ve been dating online, I’ve thought about an article I read years ago, written by one of my favorite authors, Anne Lamott about her own experiences on She wrote it in 2013, when she was 60. At the time, I was 49 and in a relationship. I made the same assumptions she did – that if I were going to date again it would be the same as when I was younger – plenty of single, liberal, kind and funny guys to meet.

I have to admit, I now find the article a little depressing. Anne Lamott is a wildly successful and brilliant writer; she’s cool and funny and fascinating and good. If she has trouble dating, what about me? However, like the great Anne Lamott, I remain hopeful. Here are some snippets from the article…

“Heroes come in all circumstances and ages. The prophet tells us, “Your old will have visions; your young will dream dreams.” Elderly women in a retirement community in Mill Valley protested the war in Iraq on a busy thoroughfare with placards every Friday for years. A man I know of 22, halfway to a medical degree, is pursuing ballet dreams in New York City. Some people my age — extreme middle-age — train for marathons, or paddle down the Amazon, skydive, or adopt. They publish for the first time.

Me? I may have done the most heroic thing of all. I went on for a year.”

“I had experienced varying degrees of loneliness since my guy and I split up. After our breakup, I had just assumed there would be a bunch of kind, brilliant, liberal, funny guys my age to choose from. There always had been before. Surely my friends would set me up with their single friends, and besides, I am out in the public a lot doing events at bookstores and political gatherings, the ideal breeding ground for my type of guy. But I hadn’t met anyone.

People don’t know single guys my age who are looking for single women my age. A 60-year-old man does not fantasize about a 60-year-old woman. A 70-year-old man might. And an 80-year-old — ooh-la-la.

Almost everyone wonderful that my friends know is in a relationship, or gay, or cuckoo.”

The rest of the article talks about her actual year on Match, where she did not, after many many dates, find a relationship. If you want to read more, it’s at

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