That Time I Dated a Younger Man

Note: This blog post is a sponsored conversation written by Lynn Smythe, the Founder and Chief Blogger for The Creative Cottage lifestyle blog. The opinions, thoughts, ideas and text are all mine.

Well, I always thought the term “cougar”, referring to an older woman dating a younger man, was a bit derogatory. Have I ever dated a younger man? Yes, but my first cougar dating experience took place years ago when I was going through a bit of a transition phase. I was in my mid-20s and he was in his early 20s – so not the stereotypical older, over 40 woman dating a much younger man.

Not Even Looking for Love

It was a fun relationship, but not one that I ever thought I’d start in the first place. I had recently relocated from Upstate NY to Connecticut after completing a 3-month management training program for a fabric chain store. I was given my own store, as the store manager, but quickly after making the move realized I was quite bored with the duties. And, since I also did the payroll, realized I was making just a few cents more per hour than the assistant managers. But I had a lot more responsibility and had to fill in when people called in sick, on nights, holidays and weekends. Not quite the glamorous life of fashion I thought it would be.

Anyways, after the thrill of “I’m going to be the manager of my own store” wore off, I was looking for opportunities for what else can I do with my life? I discovered there was a technology college nearby that offered computer programming or computer operating degrees in as little as 6 months. I scheduled a tour of the campus and found myself in the admissions office, signing up for the computer programming track.

cougar dating older woman kissing younger man
Looking for love on Cougar Dating sites. Image courtesy Pexels.

My Cougar Dating Story

Long story short, I never actually finished that programming course, and ended up moving back to the Adirondack Mountains – but that’s a story best left for another day. So anyways, winding the clock back to my time studying computer programming – here is the rest of My Cougar Dates story.

There was a younger boy in my class, I was guessing he was 3 to 5 years younger. We became friends but at first, I didn’t really think he was dating material. He certainly was cute, but he was the kind of good looking guy that never seemed to be lacking young women swooning all over him. I was the last person on earth I ever thought he’d be interested in saying hello to. So, imagine my surprise when our relationship turned into a friends with benefits role.

Fast and Furious in Connecticut

The relationship only lasted a few months because if you refer back to the beginning of this post, I ended up leaving Connecticut and moving back to Upstate New York. He was a lot of fun and very enthusiastic in certain areas, if you get my drift, but I knew there was no hope of a long-term relationship. One, he seemed a bit immature and he was still living at home  with his parent – not a total deal breaker, maybe he was trying to save rent money, whatever.

But he was also a heavy drinker, which I didn’t discover until a few weeks after we started dating. Again, I don’t mind someone who’s a social drinker but heavy drinking, and I suspected he may have also been using a few recreational drugs, that was a turn off. And, I don’t think I could ever get too serious – as I mentioned earlier, he always seemed to have a lot of younger girls saying “HELLO” when we went out in public so I am pretty sure I was just one of many women he was “dating”

So, besides that one time in Connecticut years ago, I’ve always dated older men – between 2 and 7 years older than me. But I would love to hear all about your cougar dating experience as an older woman dating a younger man!

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