My Cougar Dating Story

One year ago…

She’s sitting down the bar twirling a tiny straw around in high ball glass of what I presume is a gin and tonic. She’s got a tight body and is all prettied up with make-up, hair and a sexy outfit, a bit overkill if you ask me, well at least for being in a small dive bar on a Tuesday night. She’s definitely older than me, probably in her early forties, about ten to twelve more years than myself. She keeps making eyes at me; those extra long stares, some people might call it the “fuck me eyes,” but whatever it is I know there is definitely some attraction.

I flash her a few smiles and acknowledge her flirtation. At this, she rises from her bar stool and walks directly over and sits next to me. Her legs crossed in a way that exposes her upper thigh and her cleavage stretching tight against a thin black blouse. She immediately opens up to conversation, introducing herself and exclaiming how she never approaches guys at bars like this…yeaaa right! It’s at this moment that it dawns on me. She is on the prowl. Oh my god, it’s a cougar!!

I had often heard many great cougar dating stories from some of my more sexually active college friends, stories that seemed beyond the realm of possibility to me, but tonight it looked like the cougar was finally attacking my scrawny nerdy boyishly handsome self… alright maybe I’m embellishing a bit but hey, I look young!

By the way, for those that don’t know, a “cougar” is a slang term for an older woman who pursues and dates much younger men, with the age disparity usually having a gap of at least ten years or more.

The cougar dating scene has really only become in vogue recently, within the past decade, as previously this type of behavior was taboo or socially unacceptable for older women at the time. However, now cougar dating is almost catching on as a fad. It seems to evolved to the point where it’s a sign of power and individuality for those older women. Some of them are divorcees simply looking to have fun, not ready to settle down again. Some are high powered executives who are more dominant and looking for a boy toy. I can’t really say where the term cougar came from but it seems to fit well as a metaphor for this type of womanly behavior.

Ok, lets get back to my story…

Finally, after she buys me multiple rounds of drinks and we have a lengthy yet flirtatious conversation, we end up back at my place…yadda yadda yadda… I now have my own cougar. Well actually she has me.

The next couple months go great. Basically she calls me on random nights when she’s feeling energetic, it’s always on her terms, but the best part is she always buys when we go out, or brings me beer or wine when she comes over. It’s almost like have a sugarmama I suppose.

Whatever type of relationship we have, it’s certainly not a serious one and it can’t last. And as with most cougar dating stories this one ends up with an unemotional and mutual ending. I can’t say that it was one of the most meaningful relationship I’ve had, it wasn’t at all, but holy shit, the sex was fantastic!

Present day…

So that little gem of a story occurred well over a year ago now. I’m not really looking for anything like that now. I really want more of a committed relationship a little closer to my age range, which is why I am still scouring the online dating scene. The experience was certainly nice though for a little fling and I learned a lot in the bedroom as well, which really helped me out. So in that respect, for you single younger guys out there looking for a little more experience I actually recommend finding yourself, or at least being prey, to lovely older woman.

There are even niche online dating sites popping up these days devoted particularly to cougar dating to help make the process more efficient. Hell you could probably even find plenty of them on free dating sites like Plenty of Fish if you look hard enough.

4 thoughts on “My Cougar Dating Story

  1. Some women that are referred to as COUGARS,just like younger men,for me it has nothing to do with SEX,its the way a women feels inside,and attraction,just because our outside ages and our chronological age climbs,doesn't mean we can't love or fall in love with or have and absolute satisfying relationship with a younger man. When I was 33 I married someone 21. It can work and in fact the younger men on POF that are in there late 30's 40's are actually pursueing me,and y'all where Boy Toys in the 80's and 90's and it was Cosmo,NO one refers to Demi Moore as a cougar and Ashton was 27 and she was 42 when they got married, No one has EVER referred to Susan Sarandon as a Cougar,with Tim Robbins,or Mary Tyler Moore and her Heart Surgeon Husband or Joan Collins and her 20 plus younger husband or Liz Taylor when she married Larry,COME ON,who made you a literary writer and an expert, WE like who and what we like…C

  2. @Anonymous,

    Relax, I'm not saying there is anything wrong with an older woman dating a younger man. If I had felt a strong connection with the woman in this story than I'm sure we could have gone on to have a great relationship, but there wasn't a real emotional spark there.

    The fact is that the lexicon for an older woman dating/having a relationship with a younger man is called a "Cougar." Pop culture has determined this and so it is. Again, I'm not saying there is anything wrong with it.

    Also, if you do a Google search for famous celebrity cougars, all of the names you mention above: Demi Moore, Susan Sarandon, Mary Tyler Moore, Joan Collins and Liz Taylor have INDEED been referred to as Cougars by many pop culture websites, so you're simply wrong with your statement that no one refers to them as cougars, they do!

    As for who made me a literary writer and expert? No one! This is MY blog and this is the stuff I write about. I don't make any claims to be an expert, I just write about things that interest me concerning topics on dating, relationships and obviously online dating.

  3. I’ve noticed more women that are a bit older than me contacting me on POF lately. I’m not sure if the show ‘Cougar Town’ is making women more bold or what’s going on.

    I recently talked to a woman with about the same age differences between her and myself you described above. (She contacted me first and definitely was the aggressor.) She looked great, but I decided it was not for me and passed.

    I’m sure it would be a lot of fun, but I like my women around my age (up or down a few years).
    .-= Brandon DuranĀ“s last blog ..Weeding Out Uninterested Women =-.

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