Roar, Growl, Cougar Prowl: The Night I Officially Became A Cougar

I’ve always had a really big problem with dating younger guys. I’ve only done it a few times, and I was never happy about it. Similar to my attraction to guys who are tall and strong, I guess I just have this idea that a guy is supposed to be older than me. This post is about how that idea goes out the window when that younger guy looks like a model and has an awesome personality.

Once, on a vacation, I met a guy (who I’ll call Billy) that was 3 years younger than me. I walked into a club, which had about 10 people in it at the time and there he was, standing there staring at me with his “serial killer stare” as I later referred to it, haha. After playing Peek-A-Boo for a little while, I decided that I was going to pick him up. (And, the funny part was: I used those exact words in my head without knowing his age yet.)

The next time Billy looked at me, I smiled at him — and he smiled back. This occurred two more times before I eventually left my friends and walked over to the bar to “get a napkin” (because, ya know, two just isn’t enough to hold a Malibu Bay Breeze). I turned around to face the dance floor, which was much more crowded at that point, and my eyes stopped when they locked on his.

Leaving his friends, Billy walked over to me and asked, “Are you alone?”

“Yes,” I said, with a smile.

“Do you want to take a shot with me?”


We walked back over to the bar, took our shots, and started talking.

“You like how I lured you away from your friends like that? Slick plan, huh?” I said with a smirk.

After agreeing, Billy went on to tell me that he didn’t want to appoach me because he thought one of my guy friends (who kept touching my damn arm while he was talking to me!) was my boyfriend.

I told Billy all about JenAndMen, he told me what he did, and I decided he was somehow even hotter up close. In the midst of all this, age came up. When he used my line — “How old do you think I am? — I knew I was in trouble.

“Twenty-eight?” I asked hopeful, knowing full-well that that question is never asked by a twenty-eight old.

“Nope, I’m 21,” BIlly said, smiling.

“Oh my God, you’re a child,” I said, looking up at him.

“How old are you? 23?” he asked.

“Go up,” I said, pointing to the ceiling.


“Woah, too far up! I’m 24!” I said, quickly stopping this guy from aging me any further.

“Oh, so who cares?” he said, smiling.

In my head I was thinking, I care. Walk away. Go ahead, start walking. You’re not moving yet. Okay, now. Alright, nowBut my feet wouldn’t do it. Even they recognized how awesome this guy was, 21 or not.

We ended up talking and dancing in the club for the next two and a half hours. Half way through that time, I let Billy know that I was going to make out with him at some point in the night, and he laughed.

“You’re crazy, you know that?” he said, smiling, and gave me a kiss on my forehead.

“And you’re crazier, because you’re hanging out with me,” I said, smiling up at him. I decided that his height-to-age ratio evened out and that he was actually my age if you factored in how much taller he was than me. It makes perfect sense, really. Really.

All of a sudden, a guy began elbowing Billy in his back and he was getting visibly angry.

“Wanna see me diffuse a bad situation?” I asked him.

“Umm, sure,” he said, looking confused.

And I reached up on my tippy-toes and kissed him.  I figured, Hey, if I’m gonna be a cougar and pick up a younger man, I should do it right.

We ended up leaving the club and spending the next three and a half hours sitting at a nearby bar together, eating and talking. I realized there that we had an actual connection — not just a club romance. He made me realize two things: (1) Younger guys aren’t so bad, after all & (2) Maybe not all guys are assholes… Okay, okay. Let’s not get crazy. All guys are assholes. But perhaps not all the time.

Ladies: Ever date a younger guy and feel like a cougar? Guys: Ever date an older woman/ cougar?

3 thoughts on “Roar, Growl, Cougar Prowl: The Night I Officially Became A Cougar

  1. I once dated a guy two years younger and as much as I tried to overlook the fact that I was older, I just couldn’t. Don’t get me wrong, he was so cool and laid back (not a lazy hack). I always caught myself amazed at how mature he was. He was into the “older women” thing so it worked out for a few dates.

  2. I have had several serious relationships with men that were at least 5 yrs younger than me and I’ve learned my lesson. They don’t work out because we are at different places in our lives and want drastically different things out of the relationship. Fun for a short run, but definitely not recommended if you’re looking towards the long haul!

  3. Kimberly: I’m sorry it didn’t work out — and I love how you threw in that he wasn’t a lazy hack, haha!!!

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