Cougar Dating Stories from Around the Web

Cougar Dating Stories from Around the Web

In honour of Brigitte and Emmanuel Macron, France’s new First Cougar and Cub, we decided to put together some of our favourite cougar stories from around the web.

Dating a cougar is tough but rewarding, and these stories are here to show you why it’s worth the effort! Just ask Macron. His French and Latin teacher at high school, 24 years and 8 months his senior, captivated his imagination so much that, years later, they wed. His stepchildren are roughly his own age.

While we’re not suggesting you go that far, there’s a lot to be said for dating a cougar.

A 52-year-old woman claims to be the UK’s top cougar. Her story was featured in several UK tabloids over the last few years. Juney Smith has dated more than 250 younger men since she turned 30—she says it keeps her young, and that men her age can’t offer what young men can and have no idea how to date properly!

“I have always dated younger but really focused on it from the age of 30. Among the guys I’ve gone out with were teens lads aged 18 to 20,” she said in the story. “I haven’t looked back since. I tried dating men my own age but they are boring, bad in bed and frankly not eager to please. After a divorce they return to the dating scene and simply are out of their depth. They have missed out on a generation of dating changes.”

Self-described ‘Cubs’ of Reddit shared their stories on a thread about meeting and dating cougars [NSFW]. One 24-year-old started a thread to tell a story about his experiences. He was playing pool at a bar with some women, he says, and ended up getting one of their numbers and hooking up at her place.

He said: “I stayed the night and we ended up talking until daylight. I found the conversation some of the most engaging I have had in a romantic setting in years. One thing that sticks out the most to me […] was how she found intelligence attractive.”

A recurring theme, in real-life stories of cougar dating from around the web, is how more mature women find different things attractive from their younger counterparts. This story has a happy ending. The 24-year-old finishes his Reddit post with: “At first, I shrugged the encounter off as just a one night stand, and chance fling, but for weeks, I could not get her and the night we had out of my head. […] We hung out for probably 4 or 5 hours, swapping stories in between some physical fun. We had another great time, and even though she said many times that she never sees herself remarrying(the divorce and having older kids is giving her a mental block), I could see myself out on dates with her, in public, instead of sneaking around, getting our time together when her kids were with their dad.
Now I come here, to share my story, to give hope that maybe one day you too will find what I did, even though I wasn’t really looking. This situation was not something I ever even dreamed about, but I am glad for it.”

Another cub, this time a 26-year-old, started a Reddit thread to share his experience of and ask for advice about getting involved with a woman, a family friend just over 20 years his senior (Macron territory now). He says the woman had been a crush of his since his teens that he had “practically given up on”.

“I’ve known Carol since I was 15, but for obvious reasons didn’t come out with it; not only was she older, but she was also friendly with my parents. I never told her anything about it until I was 17 […]I made a desperately juvenile attempt to tell her how I felt with a flowery love letter.”

He picks up the story years later:

“About a month and a half back, Carol moved back to town […] Carol mentioned the town had changed a lot, and I saw that as an opportunity, offering to show her around a bit and get her reacquainted as she was moving in with her parents until she got a place to stay. We spent two or so weeks meeting up, though there wasn’t any kind of flirtation from her and I thought I ought to respect that and kept my impulse to do so in check. Then, one night, I was in town looking for something for dinner and thought I’d playfully check if she wanted to join me. Half an hour later, we were chatting again and sharing anecdotes in a restaurant, and by nine we had ended up in bed together.”

We ship them. In fact, we want six seasons and a movie. Someone get Nicole Kidman’s agent on the phone.

Another cub:

“One night my co-worker went to bed early and the wine just kept flowing. Next thing I know we’re just sitting there staring at each other after a good laugh, and she breaks the silence with “is this really going to happen”… ALL FUCKING NIGHT IT DID!”

He calls the sex “mind-boggling” and summarises: “make her feel like she’s 20 again and she will bestow a treasure trove of under-the-sheets knowledge you didn’t even know there were names for.”

Recent divorcees make up a good portion of the real-life cougar stories from the web. One casino employee took to Reddit to fondly remember a former boss:

“I found out she was recently divorced, 38yrs old and she was enjoying/exploring her freedom. I bought her drinks, she had lots of fun and I got her number. From then on we got to know each other better and eventually became fwbs for about 9 months. It was amazing best sex I’ve had at the point of my life. We were always having sex or fondling each other. We even fucked in her office a couple of times when she needed that lunch time fix. It was just incredible. My young mind was blown that’s for sure.”

In fact, bosses taking advantage of their young hires was a bit of a theme as well.

“I was 20, she was 41. She hired me. 1 year later she quit to pursue another career. We’re 2 years strong right now. Best. Sex. Ever. I had multiple partners before her, I can verify. Older women tend to know their bodies a LOT better. If she gets into flirting with you, unless you dunce it up, your chances are probably quite high. She knows what she wants, don’t kid yourself into thinking you’re the one ‘hunting her.’”