Hi ladies, I would really like your advice on one thing I have never really been able to comprehend and don't see myself realistically ever mastering.

My story: Bullying during childhood > no confidence > don't know how to initiate a conversation > loner who dates less than one day per year, on average. You get the idea.

So, I think it comes down to the fact that, even though (I've been told countless times) I am a fairly good looking and intelligent well-rounded guy ... 6 ft tall, in great physical shape, almost always well dressed, with nice skin and a great smile, I'm almost never able to muster the confidence to initiate a conversation with a girl I find attractive or interesting. On the rare occasions when I can start a conversation, I can't keep it going very long, and it falls flat. I'm never able to take it to the point of "So, let's keep in touch. Can I get your email/phone ?". That leaves me feeling disappointed and sad, because I feel like there was a chance for a friendship or more, with an interesting gal, that I lost, and I don't know why ! I don't know what I did wrong, and I don't know what I could/should have done differently that would have resulted in success.

So, my question(s) to you: Imagine yourself, a single gal, in a bookstore. What are some of the things that you would like to be asked or that you would like to talk about with a guy who initiates a conversation with you ? Also, what can he do to keep you interested and engaged in the conversation ? Under what circumstances would you then take the leap of faith to give him your contact info so you guys could keep in touch ? What are the things you would look for, in this guy, given that it's your first time meeting him ? What kinds of things about him would leave a good impression on you ?

Thanks, I love y'all