Dating Cougars: How Old is Too Old?

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I’ve seen the 1971 classic Harold and Maude and think it’s awesome. But dating a woman my granny’s age is a bit of a spine-tingler. For a guy in his 20s, at what point is a woman simply too old?

In Cougartown, 40s is the ideal. She’s got her shit together, and is still young enough to cash in. She’s a “new” cougar, ready to go, and raring to max-out on her new status.

Even a woman in her 50s is still a serious contender—especially for guys in their 30s. By 50, all those qualities we love in a Cougar (confidence, experience, know-how) burst at the seams. Trouble is, those seams ain’t what they used to be. Despite a countlessly fair amount of exceptions, nature takes its course, and it’s only to be expected that an older woman’s body will lose some its luster. (Again, many women do a fine job of keeping fit, and continue to look great, but time is time, and it does what it does.) The Golden Decade is generally a trade-off: body VS  what it can do.

Personally, I can find both 40s and 50s appealing, and I’ll leave the door open to either option, depending on the vibe.

But a woman in her 60s? Or older? No way. As a guy in my 20s, the thought of getting frisky with a woman who’s old enough to remind me of walking hand-in-hand to my first day of kindergarten, or unwrapping Lego on snowy Xmas mornings, is something I find unsettling. When I pull into a restaurant parking lot with my date, I don’t want to be worrying about having her slipping on ice and breaking a hip

None of this is to say that women (or men!) 60+ shouldn’t date—they should! they should!—but at some point the gap has to close.

I have a general rule of thumb: if the hot flashes have ended, so has the romance…


What is your age difference maximum when dating an older woman?

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