One of my friends wants me to go to her house and role play talking to men. I told her I don't have trouble talking to men, I just can't figure out how to move it past a casual talk with someone I find interesting.
Sunday at Huffines Art Trails is a good example. I was bebopping along when one of the policemen on duty called me over and started asking me questions and talking to me. He was quite handsome, probably close to my age, and funny. We talked a few minutes, and then I told him to have a good day and went to another booth. When I came out of the booth he was there again and called me over again. A little chit chat and I went on to another booth. When I came out we spoke again. During that part of the conversation he asked me what I was going to do for dinner. I told him I was going to go pick up my son on campus and take him out to eat. He proceeded to tell me about a meal he had that was delicious, a little more chit chat and then I said I had more of the trails to finish.
After I walked around for another 15 minutes I got to wondering if I could have taken that conversation in a different direction to see if maybe he was interested in talking some more in another venue. Then I realized I don't know how to do that in this life. When I was in high school and college it was not an issue. I mean you would meet a guy, find him interesting, and then mention you would be at the basketball or football game, the student union, the campus movie, etc., and if the guy was interested he would show up where you were. That won't work at this stage of my life.
I don't think role playing will solve my problem. I think getting up the nerve to suggest to the next guy I find interesting that we talk again sometime might work. The key words being "getting up the nerve."