Missed opportunities

Last night my friend Jason, my nephew David and I all went out to Champs to watch the basketball game. What looked like a blowout turned out being a very close game and we had a good time cheering on both teams. Maybe the best part of the night was our waitress, a very cute, friendly brunette named Natalie. Now I never can tell when a waitress is flirting because they like me or if they simply want a good tip but it seemed like there was a connection between us. But instead of asking for her number I left a big tip and walked away. This is becoming an increasingly familiar pattern in my life of missing potential opportunities with women.

Last summer I met an amazing woman on a flight from Chicago. We talked the whole way, had lots in common. I am sure she was interested in me but I chickened out at the last minute and didn't ask for her number and now have no way to contact her. I regret it to this day. Then last Fall I was afraid of committing to a good friend of mine. We had been "hanging out" all year and she was really cool, smart and attractive but every time she would try to move things along romantically, I would get cold feet and pull away. Now I regret that I didn't give that relationship a chance.

Last night, Jason and I were talking and both complaining about not dating. The problem is we have been having this same talk for ten years. I fear it will be the exact same talk another ten years from now. When I was younger, I was okay with being free and having no commitments. I had plenty of time to find Ms. Right and I could pretend that when I was thirty I would settle down and find someone. Now it is not so fun. I fear that I am living a life of regret because of my fear of rejection and commitment. What if I have already walked away from my perfect woman because I was too scared to pursue her? What am I waiting for? How do I break this pattern? They say insanity is doing something over and over again even though it doesn't work. I think I am going crazy.