Sex and the (slightly older) Woman, Pt. 5

If a man waits until you are both naked and sweaty to ask, “what do you like?” he is clearly working with only the most primitive intuition, and should be sent back to junior high school.


The correct time to ask is when you meet. Correction – don’t even ask – LISTEN.  It’s all right there: in the profile, on the phone, at the bar. It should be apparent if a woman is the wine and roses type (really, who isn’t?), just wants a good laugh (who doesn’t?) or maybe seeks an adventure (why else would she be here?). THIS is foreplay. 

The chatter, the nervous laughter, the tentative touches and the broad smiles might lead to what we really want. Because both parties are after the same thing, some iteration of love. And the bold “mature adult” impetuous enough to try to replicate actions and emotions more wisely left to earnest and guileless teens deserves what he or she really wants.   

It’s in every romance movie made.  Women want to feel attractive,
amusing, interesting. Men want (I think) to feel smart, admired and in control. We owe each other respect and honesty. Then we can get to the good stuff.  

It has to start with clothes on:  Taking the time to select a destination based on my preferences.  Whispered intentions over dinner will make any woman warm. Making accurate reference to something I have mentioned, terrific. And if a guy just can’t help himself from planting a kiss behind my ear at the coat check, brilliant.  But telling me he can’t get enough of me, priceless.  

Of course, all this titillation can only work if both parties feel a frisson when thinking of one another.  And sadly nine out of ten dates have provided more of a shudder.  Oh but that one…

Such simple tips to basic satisfaction. Just figuring this out, and writing it down, has given me hope for a future tryst. One in which there is no thinking about laundry, when “thinking” should the last thing on my mind.


  1. Interesting column. The Loop getting a bit racy. What’s up with that? I think it’s a better read than the Police Blotter.

  2. I enjoy reading your column. Looking forward to part 6.

  3. Witty and wonderful. Can’t wait for the next installment.

  4. I love you – are you free this Saturday night? hey, no kidding, great, fascinating column! Good luck!

  5. such a fun read…straight from the heart and so easily captures the trials and errors of dating at 50….can’t wait for part 6!

  6. Great read! ๐Ÿ˜€

  7. There I was walking around the Upper Westside at nine-thirty in the morning one Saturday a few decades ago when I run into my old buddy, Glen. For a nice guy, Glen is one of the nicest. Always looking for the perfect girlfriend to turn into the perfect wife. I mean, that’s what he wants and he is way good looking, so I figure that’s what he should get. Right? But it’s not that easy. We’re talking New York City women who always come with a coefficient of neurosis way over one. So Glen tells me about the five women he has dated in succession over the past two years since I’ve seen him last. His sincerity is pouring over me like that cold can of maple syrup that’s been waiting in the Frigidaire for years which I finally used on yesterdays French Toast. I felt like the character in the book Cad: Confessions of a Toxic Bachelor, but it hadn’t been written yet. So I tell Glen about the five women I’ve dated the past two years all concurrently. Sure the Wednesday night girlfriend wants to know why she doesn’t see me on Saturdays. And what do I say? Heck I don’t remember รขโ‚ฌโ€ I was a emotional retard. I figured I needed a bunch of relationships, make a bunch of mistakes, learn a bunch from my mistakes and try to learn some emotional spontaneity which I’d hope would be better that waiting three or four days to figure out how I felt about anything.

  8. Quite the following Anon!!

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