This Cougar dating story doesn’t involve me. It involves my best friend, Greg. About 6 months ago, I approached Greg about signing up for an Internet dating site. He’s had 1 girlfriend in his life, and that was about 5 years ago. Let me give you some background on Greg. He’s 26, never married, no kids, had sex only a handful of times in his life, has a good paying job, is smart, isn’t very good looking, and lacks confidence. That’s not a good combination to have if you want to get laid – especially with Cougars.
I had originally intended on helping Greg sign-up for a regular Internet dating site, where he could meet women his own age. So we got him signed up for PassionSearch.com. He had no success attracting 20-something women. I didn’t even think about having him go after Cougars. But after a few weeks of attempting to find him someone, I was ready to just give up. Women just were not digging him. That’s when I asked him what he thought about dating older women. I didn’t even know this, but he said he had always fantasized about being with an older woman. PERFECT!
Since I’m an expert with Cougars, I figured I would be able to better help him meet someone. The first few days were a little rough. He didn’t get much response. But then, out of nowhere, a gorgeous lady contacted him. She sent him an email that mentioned how interesting he seemed in his profile. She didn’t even mention his appearance. She seemed willing to look past that.
I sat next to him as he chatted with her via Instant Messenger. I even helped him out with many of the answers. Then I told him why I was telling him to say what I was telling him to say. After a bit, he was starting to catch on and my help was no longer needed. This woman got my shy, nerdy friend to open up. And once he started to open up, he became quite confident. He really does have a great personality, but he is too afraid to let strangers know of that personality.
Dude absolutely nailed it with this gal. Within 2 hours of conversation, they had a date set-up. I didn’t even tell him how to ask for the date. He just did asked with confidence. They agreed to meet that weekend at a Martini Bar in town. I was ecstatic but I knew I better calm my enthusiasm until AFTER the date. He still needed to impress her in person.
When he left my place to go meet her, I was probably more nervous than him. I really didn’t know what to expect. An hour after he left, I somewhat expected a call from him saying that she ditched him. That didn’t happen. In fact, I didn’t even hear from him until the next day. Either he was pissed off and didn’t want to talk about what went on. Or he was getting laid. I hoped for the latter, but expected the former. It turned out to be the latter. He ended his dryspell and proved that even nerdy guys can hookup with hot Cougars if they know what they’re doing.