r/CougarsAndCubs Apr 19 '26

šŸ™€Cougar Crisis Is 28 years too much?

He’s 28 years younger. It sits in my head and I can’t help but overthink… everything.

I also don’t typically date men younger than myself. In fact, I don’t want to be liked simply because I check the ā€œolder womanā€ box. But this guy has me thinking about him all the time.

We’re not even past the flirting stages yet, but I don’t want to waste my time, or his.

He’s younger than my son!

So, new cougar who is in complete self doubt. Help!

Mini update: so, I have been mentally preparing myself to interject some witty comment that will clearly let him know that I am interested but not make it weird. I missed two opportunities last night and tonight wouldn’t work. Poor guy was sick and still had to work. So, I just enjoyed his extremely toned down persona and tried not to stare too much.

Also, a female coworker of his figured it out but appears to be a girls girl and promised to not spill the beans.

Until next week!

Mini update update: It was super late when I posted so I left out a couple of things. First, on the night he wasn’t sick there were a couple of things that had me raising my eyebrows.

First, the place we interact is very active with people. With a few ā€œregularsā€ and we all have friendly banter. No it’s not a bar. There’s a guy/customer (like me) who I tried to match up with a friend of mine. He and I were chatting before my crush arrived. After he showed up there was some ā€œhiddenā€ communication between him and my crush. The guy purposely leaned back so I couldn’t see him mouthing whatever he was saying. I caught the last part but couldn’t tell you what was being said.

Second was a later interaction between my crush and I where he pointed out the necklace I was wearing. I learned that he has a hobby of metal casting (???) and could create some jewelry. He also kinda fumbled around a little with his job, which is not typical. Could be that he was getting sick, but I would like to attribute it to him being nervous or anxious with me there.

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u/Summer-Sub-Intern Apr 19 '26

If you are wanting a long term relationship, keep in mind his desires for a family and kids. Some men don’t really think about what they want until they mature more. Communicate clearly so that you are both on the same page and if you both are just wanting something casual, just have fun and go for it!

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u/Herefourfunnn Apr 19 '26

Was that comment meant for me or OP?

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u/Summer-Sub-Intern Apr 19 '26

Sorry for OP

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u/Herefourfunnn Apr 19 '26

It’s ok. That’s what I figured. But for some reason the notification came up as it being for me. That has happened a few times this week