Dating : On Becoming A Reluctant Cougar

I never meant for it to happen. It started when I was so young, I didn’t think being a ‘cougar’ would last for the rest of my life.

Who, as a girl in her 20s, would ever imagine themselves going from dating guys a few years younger to becoming a full blown cougar? Can you even be considered a cougar before you turn 40 ( I checked the rule book, you can’t; you have to start off as a Puma)? If anything, in my 20s and 30s, I felt like a freak, like there was something horribly wrong with me. No matter how many crushes I had on guys my age, they were simply NOT interested in me, but younger guys were. And those younger guys weren’t shy about their interest in me either. So I sucked it up, prepared myself to take a lot of shit from my friends, and started dating younger guys, despite my own reservations.

It started small; I dated guys anywhere from 2–5 years younger. When I was 23, I married a guy who was 21. Our marriage didn’t last long, and as I grew older, the age difference between myself and the guys I dated grew larger and larger.

My first serious relationship with a major age gap (9 years) occurred when I was 28. I had just gone through a divorce and Matt starting flirting and actively pursuing me, making me feel more desirable and appreciated than I had in years. He was attractive, he was a talented musician, and he treated me better than anyone else ever had, so obviously I fell for him pretty hard. Everything happened so quickly, I didn’t even have time to worry about the difference in our ages or how other people would judge it.

Fast forward to us moving in together after a couple of years of dating. Matt was 21 and I was a divorced, older woman, so you can imagine his parent’s delight! One day while he was at work, Matt’s mom dropped in unexpectedly. She wanted to know what it was that I saw in him, and how I could possibly take our relationship seriously with such a big age gap. I’m not sure how convinced she was by my answer, but I earnestly explained that I loved how talented, intelligent, and passionate he was about the things he loved. And that we had a connection that I’d never felt with anyone else I had dated, of any age. This was my first experience with mothers openly doubting my intentions with their sons though it was to become a recurring theme in my life.

Although Matt and I eventually parted ways, I still think of my relationship with him as the most significant romantic connection in my life, and he set the bar pretty high for anyone who followed.

So why *do* I date younger guys? The answer is much less salacious than you might imagine; most people think it’s all about the sex (which I’ll be covering in future articles), but it’s always boiled down to who I feel most connected to, who I share common interests with, who can match my energy, and maybe most importantly, who it is that pursues me.

I’ve never been one to make the first move, and whether it’s in real life or on dating apps, younger guys are consistently the guys that approach me most often. It would be much more convenient for me to date someone my age (and I’ve tried); there wouldn’t be any teasing from friends or worried comments from my parents, and I’d feel more confident and hopeful about a potential future together. But this just isn’t the way my life has worked out.

I’m 52 now, and the last guy I had serious feelings for was 35. Though ultimiately our relationship didn’t work, he did (pretty informally; we were standing at a bar, day drinking on Valentine’s Day. The romance!) ask me to marry him, and I said yes. While I’m grateful that our plan to get married didn’t pan out, I often worry that he was the last guy who could see past the looming expiration date that most people see when they date someone with a notable age difference, and would be willing to explore a serious relationship with me.

It’s difficult to be a cougar who actually wants to settle down (more about that coming soon!), and I often question the reality of being able to find the ‘happily ever after’ that so many of us seek. When I’m trying to puzzle out the odds of finding that ending, my brain tells me that it doesn’t seem too likely, while it’s in my heart’s nature to be hopeful. So I’ll continue to follow my heart for as long as I continue to date, no matter how old I get.

Follow me and stay tuned to hear more insights and adventures of dating as a cougar!