1.) Ask him back to your place for drinks and a rousing game of "hide the salami."

2.) There is no 2.

As a male, and a shy one, I had difficulty for years. I'm not sure what tripped the "On" switch, but when I started, I had tremendous success. I was, at best, average looking, a little overweight, hair turning grey, and sure I would never attract a pretty woman. All of a sudden, I got confidence from somewhere, and found that the only thing stopping ne from picking up the best-looking girl in the place, was that I hadn't yet started talking to her. The best women, beautiful or not, are not all looking for the "hunks" – they want someone who will appreciate them and make them feel good about themselves. And guys: no matter what, NEVER take your eyes away from her eyes! Even if she stands there and takes all of her clothes off – just stare into her eyes, and smile like a kid in front of a loaded Christmas tree. The time for looking lower will come in due time – just let her know that you are completely into knowing her! I, a plain-looking, pudgy, greying shy guy, dated a lot of really great-looking girls, and ended up married to absolutely the most beautiful (no exaggeration!) and most wonderful girl I had ever seen in my life!