How to Engage With an Older Woman (And Not Piss Her Off)

Yesterday was fabulous. I went out. Without my laptop, without a plan, and not very far from home. After a week of endless parenting duties and a devilish dose of stress, I finished my morning writing, closed the computer, grabbed cute shoes and made a beeline for… wherever I might end up.

Sarah Jessica Parker 2009Where might that be?

Sex and the City 2

My not-so-back-of-the-mind destination? A nearby mall where Sex and the City 2 would be playing. Hourly. I have commentary on the movie – but I’ll save that, for now. I will mention that spending a few hours with Carrie, Samantha, Charlotte, Miranda – not to mention Big and Aidan – was delightful.

Fashion? Stunning interiors? Lavish scenes and sets? Cougar action? There was plenty. Pearls of wisdom? One or two.

More to the point – uncharacteristically – I blew off every “must do” and went with the flow. Hung with “the girls.” And mused afterward on the issues of older women and younger men, conjuring a few tips of my own that might come in handy for any man even considering picking up, hooking up, or cooking up some play time with “an older woman.” Or for that matter, any woman.

Was I inspired by the movie? Perhaps. By other surprises that occur in life? (We’ll see…)

Let’s just say – what better, than a few timely tidbits on turning tepid into torrid, when it comes to male-female interaction? Or penetrating the secrets of heterosexual engagement, no matter what the age combination? Cougar Town or otherwise?

What is an “older” woman? What qualifies as a “Cougar” anyway?

Wasn’t the “cougar” term coined to capture an older woman of money, with a predatory nature? (Shudder.) Would an older man with money who prefers his women youthful be labeled in any way at all?

40 year old woman laughingAs for the use of “older woman” as a term, it carries less stigma. I was amused (and dismayed) when I searched on famous older woman-younger man couples, and found that one year, two year, and three year age differences were included. (Are you kidding me?) The fact that Julia Roberts is one year older than husband Danny Moder? Is this really worthy of mention?

As a potentially “older woman” I do not consider myself a cougar. I am a woman, not “predatory,” with a certain perspective on relationships that work for me, including on the older woman-younger man combination. So here goes. And yes, with a twinkle in my not-quite-elderly eye.

  • If you’re a 19-year old man and having a fling with a 29-year old woman (how French), listen and learn. All the ladies to come? They’ll thank you for it.
  • A five year spread doesn’t qualify. Unless you (the boy-man) are under age, and then… on this side of the Atlantic, no comment.
  • An eight to ten year age difference, if life were fair, shouldn’t count. How often do 40-year old men date 30-year old women? Exactly.
  • But in the real world, a 30-year old man involved with a 40-year old woman turns heads (if anyone knows).
  • 10 years or more? Okay. I buy it. Older woman-younger man. Does it matter, unless there are issues of biological clock? It’s individual preference, no?

In case you were wondering, my preference is a man at my same stage of life – with teenagers or college-age kids. Still sexual. Still working. Still hungry for life’s adventures. Experiences and reference points in common. How does that translate, typically? Approximately my age, to five or six years younger.

Special case: Fat Wallet Syndrome

Think money can’t buy you love? Think again.

In the real world, money can buy you love, or some semblance of it. When a fat wallet insinuates itself into the equation, all bets are off. 65-year old men hook up with 30-year old women, and win their fair hands in trophy-wifedom, or any other games people play. It’s routine. It’s security. It’s an exchange of services (as in all relationships) – not to mention luxury goods, generous gems, and yes – sometimes – genuine feeling for each other.

Stack of braceletsA 65-year old woman and 30-year old man? Or 40-year old man? She definitely qualifies as an older woman, but even bank won’t help, with the rare exception.

A woman’s fat wallet, or at the very least – financial independence – will, however, “afford her” a greater range of options.

Do you find these observations cynical? Realistic, in my book.

Men: Tips to impress an older woman

Hot for a woman who may have a few years on you? Eight? Ten?

As a woman of a certain age who has been approached by younger men, and yes – involved with a few, might I suggest the following tips?

  • Don’t refer to her as any sort of feline creature. You know. The C word (Cougar). In fact, C words should be stricken from your language.
  • Exceptional acceptable C words: Anything that involves Cute (butt), Cultured (pearls), Caring (woman), Captivating (beauty), or Creative (in bed).
  • Otherwise, restrict cat-like references to her sultry movement – gliding across a room, on the dance floor, or in closer proximity. Also allowed (depending upon the woman): regional references, only in the most complimentary fashion, and aptly timed.
  • Never suggest a cosmetic procedure, ask “what’s that?” or offer tweezers as a surprise gift.
  • Never, never, never say: “You look great… for your age.
  • If she mentions a dead president you haven’t heard of, reconsider. You’ll both be better off.

As for Sex and the City 2, my thoughts are here.

Image of Sarah Jessica Parker, Wiki, by David Shankbone, CC License 3.0 attribution.


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    • BigLittleWolf says

      SO glad you laughed! (I was hoping the twinkle in my eye would translate on the flat page…)

      I think I will have a slightly different perspective on SATC 2. Closer to an alternative approach that would’ve made for an interesting viewing experience. I will say, when expectations (of anything) run high, you are more likely to be disappointed.

  1. says

    Love your observations of the C word.

    Love, attraction and mutual compatibility are where you find them. And Oh, the money thing, makes finding the above all the easier.
    Have Fun,

    P.S. Sex in the City two … I think I’ll wait for netflix unless the girls really, really want to see it in theater

  2. says

    Love the tips! I’m generally oblivious to age differences in couples (for someone vertically challenged, I notice height differences more often). But I did find myself, uncharacterstically protective of an older wealthy male friend who married a much younger woman. It surprised me because normally, I start out on the side of the woman, any woman.
    Can’t wait to hear your commentary on SATC2! I’m hoping to catch a matinee this holiday weekend!

    • BigLittleWolf says

      Belinda. What a chuckle. As I have typically dated men 12 to 18″ taller, I know what you mean…

      As for SATC 2, I hope you enjoy it. I’m purposely holding off a little, because many haven’t seen it yet.

  3. says

    My Guy is 8 years younger, and it’s the best relationship I’ve ever had – 8 doesn’t seem like many except he was in college and I was an established “career woman” when we met…it mattered. To others anyway. We were too busy with each other to care.

    Going on 5 years now – we’ve heard and made every age joke there is out there and I’d like to think that I was that “C” word before Hollywood decided to glamorize it. And if not, no big. Not looking to set any trends; just happy that I found someone whose zest for life, passion and sense of humor mean more to me than his age and wallet. Together, we have struck a balance – I feel younger, and he feels older, so we meet somewhere in between :)

    • BigLittleWolf says

      Lucky (and smart) woman, Justine! A good relationship is a good relationship. Period. Or rather, as Sarah would say: !!!

  4. says

    Money can’t buy love, but it sure can buy lust. Better to come together, whatever the (legal) age, based on something other than money.

    • BigLittleWolf says

      At the very least, money can reduce barriers and increase probabilities that may lead to all kinds of relationships. Including love.

  5. says

    It’s hard not to hear other people’s voices and those of the culture, but it’s better to make your own independent choices — and really feeling THAT sense of liberation is one benefit of getting older!

  6. says

    Love it, LOVE it! Can we get this post made into a pamphlet and distributed worldwide?? Or at least nationwide?? I haven’t dated any younger men, but I surely would like to without it being so newsworthy.
    Glad you had a fun night out!

  7. says

    I fully intend to partake in younger men when I am “a woman of a certain age.” Provided, of course, I am single. What’s good for the goose is usually even better for the gander.

    Your tips were awesome. I second the pamphlet suggestion!

  8. says

    As a shrink I’ve gotten the inside low-down on a good number of older-woman younger man romances. Great sex, but not always… but very frequently in the young dudes, a general shallowness and narcissistic lack of communication skills or inclination tended to leave these relationships rather lack-luster after the first blush of novelty wore off for the women.

    This also got “Mrs. Robinson,” playing in my head… and made me think of being in a bar on Spring Street in the 80’s and Joe DiMaggio coming in wearing a full-length mink coat.

    It seemed that Simon and Garfunkel’s question, “Where have you gone Joe DiMaggio?” had been answered by Steely Dan’s “Black Cow.” (“down to Green Street, there you go, looking so outrageous and they tell you so.”)

    Maybe he’d have been better off going for Zazu Pitts than Marilyn Monroe.

  9. says

    First I was a MILF (my nephew cued me in on my status and I’m not going to spell it out!) and now I’m a cougar, yet the whole time I’ve been married! All this objectifying of women and painting us as somewhat desperate is so insulting.

    I do see a lot of women out there in their forties and fifties who are in great physical condition and who are aging beautifully and I see a lot of men who don’t appear the same. To me this is why it’s a proper match – the age match up is correct in everything but chronology.

  10. says

    I am struggling with my age. Not going to lie. I assumed that I would somehow have figured out the secret to being fit and fabulous by now and would just magically be awesome.

    Not so much!

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