Dating is Terrible (Especially When You’re Cougar-Aged)
7 mins read

Dating is Terrible (Especially When You’re Cougar-Aged)

A few days ago, I received a spam email addressed to Discreet Cougar. Yowzer. I am hoping I am neither, though that hope is likely in vain. My age qualifies me as a “cougar”, I know. Though whether my looks do or not is up to the beholder. Are cougars well maintained? Or just ungracefully fighting the aging process? Are they pathetic or bold? Or both? I’m not sure and is anyone really using that term anymore? Has it not yet gone the way of “disco”, “rad”, “awww snap” and “cherry”? Can’t I just be a not totally old looking 40-something rather than a “cougar” with all the desperation that term seems to conjure? In my mind’s eye, Cougars wear too much make-up, inject too much Botox, get their boobs puffed up, wear spandex or some other too tight synthetic fabrication, all in a frenzied attempt to appear younger than they are. This ungraceful endeavor is in service of wooing men much too young for them, as these ladies (who don’t look young by the way, they look their age, with fake ones) are simply unwilling to face the fact that these gents are no longer in their wheelhouse.

As far as “discreet” goes, not something I’ve ever been known for. Loud. Boisterous. Sure. Not decorous. And “discreet” has a cagey connotation, a characteristic I try to avoid.

Anyway, I deleted the email as you would with any spam. But started thinking about age and dating and the messed-up dynamic of being a 42 year old woman who has never really dated and now is faced with having to. On the men in my age range are, by and large, looking for women that top out at 35. They took their time finding that special gal, and now in their mid-40s have decided they want children! So what choice do they have but to go young.

Since I signed up I’ve gotten more emails from men 55 and up than I care to ponder. You are not my cohort! You are much older than me! Leave me alone silver fox (if you were a silver fox by the way, I might reconsider, but you are simply “grandpa”)!

Of those few that have decided they are willing to consider a woman in her 40’s, since they too are in their 40’s, my first requirement is: a job. A job that he likes. Sounds simple. But you’d be surprised. It doesn’t have to be lucrative. But he has to be passionate about it. I’ve had four first dates. No second dates. One fellow who we’ll call “Short and Angry” listed himself as a “trader” but then told me he hasn’t worked in 5 years. Eject.

First guy was under-employed. He said “self-employed” but he meant under. We’ll call him “Hippie Buddhist”. We met for coffee. It was fine. I was too … just too. He lives up North, takes graphic design projects when he finds them and is engaged in studying meditation and Buddhism. I told him I have one speed and it isn’t slow and that was about the end of that. But he sent a nice note after and it was very encouraging in that I was able to go on a date, enjoy a pleasant conversation and leave knowing I wouldn’t see him again but that there would be no awkward extrication. We’d shake hands and that would be it. Ta da!

Second guy, had a job! A great job (or so he said). He has a shorthand name as well but I won’t use it for fear of being offensive. He was ever so pleased with himself, in a way that I actually had a ton of empathy for. He’d felt criticized and not good enough for years in his marriage and now that he was outside of that dysfunction, he looked in the mirror (euphemistically) and said: Hey, I’m pretty terrific! Which would be fine. If he didn’t talk about how cute he was, and how much money he made, and then try to get me back to his place repeatedly which was not going to happen. When I was younger I could sleep with people if 1) I was drunk enough, 2) I’d harbored feelings for them for some time having eyed them around campus. I can’t do that now. There isn’t drunk enough and I’ve never seen these fellows before as San Francisco is a relatively big city. I need to be wooed. I need to fall. Not hard. But there has to be some emotional falling before the panties fall.

On to number #3. “Wine guy”. He assumed I would be endlessly fascinated by how he got into the wine game. Eh. He also seemed to have tremendous disdain for those corporate types who carry smart phones (yikes) and can afford to buy the wine he’s hocking. I don’t buy $80 bottles of wine. I’m more low key than that and I can’t taste the difference anyway. But if that’s what you’re selling and that’s what you like, you can’t hate the people that can actually pay for it. Well you can. But it seems counter-productive. Hand shake, thanks, bye.

And then came “Short and Angry” also known as “Jobless”. Who, via email, I’d had tremendously high hopes for because he seemed so smart and funny. So this one was most disappointing. I’m now taking a break to gather myself but then I will try again. None of these excursions have been the least bit painful. I’ve spent a pleasant enough 2 hours with each fellow, started out hopeful and quickly turned an about face. Which is I’m sure exactly how they felt about me, and Lord knows what nick name they’ve ascribed – I can only imagine – “Corporate Bitch with 2 Smart Phones”, “Agro Levi’s Lady”, or “Still Into Her Ex”. These are all viable appellations to assign, I suppose, without the full picture.

I remain hopeful. I will keep at it. As my friend Anna tells me (and has been said many times before), you have to kiss a lot of frogs.

Croak croak. Ribbit.

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