Hi Rich,

I’ve got to say, when I was in my 20s, I had no idea how to talk to women. I am much older, now in my 50s, and because I’m single, I’m again seeking to meet someone special.

My own opinion, FWIW, is not to try to connect with women by complimenting them. There’s nothing wrong with compliments if they come from a place of joy and authenticity, but I think if you do it to get their attention, you might be self-aware that you’re not acting authentically, and most people will pick up on that.

I’d suggest thinking in terms of having regular conversations. Don’t worry about ever seeing the women again. What I mean, is that if you’re out walking in your neighborhood and you see a woman walking a dog that strikes you, you can say “Wow, I like that dog!” You can pause to chit chat but there’s nothing wrong with just smiling and going on your way.

Do this kind of thing over and over. You can even just say “Hi” to women as you pass them and continue about your business.

The more you have lots of positive even short experiences of talking and light stuff, the more comfortable you will feel.

Here’s a goal, I’ll just toss it out there. Change it as you wish, or discard entirely: Over the next week, just smile and say “Hi” to 7 women (of any age, etc.) and for another 3 women, say something more, like “Man it’s really hot today” or, “My neighbor has a dog just like yours,” or “Isn’t it great to be outside today?”

You’re just practicing your natural ability and desire to connect with others.

Hope this spurs your own ideas!