What's the other key takeaway from my date with Ross? Don't be passive. Be aggressive in getting what you want. This is an important lesson for me. I'm too passive sometimes. What's the worst that can happen? He says no and I feel rejected. Not the end of the world. I should be confident....he might say yes.
Ross is an average guy, and really nice. I'm sure he doesn't have guys knocking his door down. He took the lead that night and it worked out.
A few years ago I went out on a first date. The guy was a little younger than me, good looking, and I would have done more with him. He was shy like me. We had a light dinner, walked around town a bit, and then got a beer. I was waiting for something to happen. Would he invite me back to his place? He seemed bored, but he was asking questions like, "how far away is your place?" and "where is your car?"
He didn't ask me back to his place. I didn't ask him back to mine. Why didn't I? Not sure, I was too shy I guess. He was shy like me. I could have, should have taken the lead here. Eventually he said good night. Lost opportunity.
I was telling a friend about this. "Rob, you are so f--ing dense! Of course he wanted to go back to your place! Why would he spend three f---ing hours with you? Why would he ask those questions?? Dude --If he wasn't interested he would have been gone within 20 minutes."
Yea, I guess you're right. Have a little sympathy for a socially awkward guy. I'm trying.