The Reluctant Cougar

Today is week four  in an almost 40-something (39) woman’s six-week journal of her “time out”. After quitting her job and spending time with her parents, she is continuing to capture what she is experiencing now and how it’s different from her 20s. Today she reflects on the sexual confidence that comes with age.

The Reluctant* Cougar**

This post is going to seem as if it is about sex, but it’s not about sex. Not really. It’s a post about self-esteem and feeling good about yourself — while, cough, having sex, end cough — and being opened minded about what may be ahead for your 20 year old self.

As the mini-retirement continues, I now find myself in the Hamptons where the pretty people play and the weather has been uncannily cooperative.  There’s not enough space in this post for all of the background and detail but the shorthand is that I was out, at a bar, doing some dancing and carousing and ended up having a one-night stand with somebody I’ll call Jacob.  (If you arrive at 39 and you’re a single lass like me, odds are you’ll have had a one night stand or 3  – so let’s leave the judgment for another blog).

Jacob is smart, sparkly and sexy because he is honest and perceptive, not because he is the “cool” guy. He asked me to dance, we kissed, we smoked too many cigarettes and drank sangria until the sun came up. And we had sex. It was fabulous.  There are three things you need to know: 1) Jacob is the guy who asks you to come back into bed because he needs to kiss your hip bones, 2) Jacob kisses you every time as if he may never get to kiss anyone again, and 3) Jacob is 20.


I was discussing what is my hilarious, head-shake-inducing little tale with my friend Ali (who wanted to know how he got into the bar and whether this is legal), and we realized that in addition to the fact that Jacob may well be some kind of sexual savant, part of the reason sex becomes more fun as you get older is that you’re more comfortable with your own body. If only I had known in my 20s that the guy wasn’t concerned about my small ta-ta’s or big bottom, or whether I had shaved my legs (sorry about that, Jacob), I would have concentrated more on how ridiculously fun it is to be romping around naked with somebody who is equally as excited to be romping around naked.  I am not suggesting I’m rid of every insecurity, but I certainly wasn’t thinking about wrinkles or fat arms when Jacob was tasting the salt on my neck after a morning swim in the bay.

If I could go back, I would want to enjoy sex more in my 20s – all of it, from loving relationship sex, to the chance encounter high-octane sex. I would try to stop thinking about what I “was” or “wasn’t” and instead pay much closer attention to how much fun and freeing sex is – for everyone at the party.

*Reluctant because it wasn’t my dream to be single at 39 – quite the contrary. I thought and hoped I would get married and have children by now.

**Hate, HATE the term cougar. Calls to mind a too-tan, chain-smoking, fake-nailed old lady pawing at some cheesy, dumb muscle-head. This was not, well…it wasn’t that. He asked me to dance, and besides, Jacob and I are both pretty pale.


It seems the real sexual liberation isn’t about freedom to have casual encounters no matter what your sex…it’s the ability to enjoy casual sex…free from the voices in your head.

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