Honestly, some may be into the whole "Cougar/Cub" thing, but in my experience, we're just considered "Young(er) Men", and they enjoy us as such.
With most scenarios, it's usually about confidence. Not cockiness or arrogance, but just being confident in yourself. Personal value-which helps with confidence-helps sell you in job interviews, college applications, or dating situations. It's all in how you present yourself.
I'll give an example. When I was 21, I went to a bar with a friend. I noticed a very attractive (older) woman on the other side of the bar, and was smitten. I wasn't really dressed to impress. I had on Adidas athletic pants, some bands graphic T-shirt, and sneakers. I watched as men in suits, or club wear approached her, and didn't seem to have any luck. After a few beers, I decided that I was going to give it a try.
I walked up to her and asked her if I could ask her a question. She said "Sure", and so I asked "How many penguins does it take to break the ice? Since it seemed that plenty had failed so far.". She laughed and acknowledged that they had, but I was welcome to "Give it a shot.". I took a seat, cracked a few more cheesy jokes, then just asked her about herself. I ended up getting her number, and we met up a few times, which inevitably lead to sex.
She was about 50, at the time, but a goddess. I was nervous for sure, which I'm sure she could tell, but I just talked to her as if I had known her already, and it worked. I was surprised, but I learned a lot from that experience.
A year or two later, I went to a hooka bar with a friend for her birthday. I again, noticed an attractive woman at the bar, just sitting alone. As we went to leave, I decided to just go say "Hi.". I walked up and asked her if she minded if I took a seat. She checked me out and said that I could. I told her that I found her to be quite beautiful, and that it was a shame that she was out on a Friday night without a date. There was an event in the city that night, and she quickly asked me if I wanted to go with her. I did have to decline because it would have been rude to bail on my friends birthday, which she said was a shame. I agreed with her, lol. We talked for maybe 15minutes after that, and I took her number and gave her mine.
Don't be intimidated man. Just go for it. Don't think about whether they'll say yes or not: Just.Go.For.It. If they say no, there will be others.
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. So, you need to have the right character, charm and brains to catch a cougar. Because even thou they seek younger guys, they do not seek mama's boys :D.
