What to Say When You Get a Cougar on IM: Chatting Your Way to an Offline Date

Cougars are more sophisticated than younger women. Therefore, you have to work a little harder to impress her than you would someone your own age. When you get her onto an Instant Message, you need to charm the hell out of her. It’s not very difficult to pull off. But your chat should be more mature than with a younger woman. The keys to impressing a Cougar on Instant Message are…

  • Making her laugh – at your jokes, not at you. Childish humor is not wise. Mature humor and light teasing are the way to go.
  • Using proper grammar and spelling. Like I said, these women are more mature than younger women and expect you to be as well.
  • Showing off your romantic side. Cougars have spent much of their adult lives without a romantic relationship. They’re looking for a romantic, passionate guy.
  • Showing her you’re confident. Confidence is the #1 trait a Cougar looks for. They can sense a guy that has no confidence. You won’t have ANY chance of getting laid if you’re not confident.
  • Paying attention to her. Cougars often spent years in a relationship with a man that completely neglected her. Take in everything she says and prove you were paying attention by following up her comments with interesting comments and questionsrelated to what she said.

     Romantic relationship

    Romantic relationship

Example of a Successful IM Chat With a Cougar

The following is an actual IM conversation I had with a Cougar I met on PassionSearch.com. The reason I am posting this is so you can see how a good conversation should go. Yes, I ended up sleeping with this woman…multiple times.

Me: Your profile says you recently moved to Las Vegas, what brought you here?

Her: When I got divorced, I decided to move here to be closer to my brother and his family.

Me: Okay, that makes sense. Vegas is a crazy place to live. Do you spend much time on the Strip.

Her: Not very much, but I definitely need to check it out.

Me: Well then you’re giving me ideas for a first date!

Her: Heck yeah! So where on the Strip would you take me?

Me: To McDonald’s, obviously!! Haha!

Her: I’d be sooo impressed if you took me there!

Me: I know, right? Perfect date! I have some less thrilling ideas, however…

Her: Oh yeah? And what are those?

Me: Start out with drinks at Venetian…

Her: That’s a good start…

Me: Then we can walk the Strip, maybe play a little Blackjack, enjoy the sights.

Her: You have me intrigued. Keep going…

Me: That’s it! Then I’ll go home and call it a night!

Her: You’re such a tease!

Me: I’m only kidding! After that, we’ll just have to see where it goes. Who knows, maybe you’ll be coming back to my place to cap the night off!

Her: I like that.