I always over thought situations when I was younger on dating girls. Some of my reasons are still valid to me but most of the time I avoided asking the question.
When we were in high school your mother and I both had a crush on each other. She was waiting for me to ask her out and I was too scared to. Luckily for us, we reconnected a few years later on MySpace and I redeemed myself. The Internet and social networks have boosted everyone’s confidence but we never had that in high school.
I was lucky when it came to your mom. Although it is hard to think about that fact that it almost never happened. My advice to you is just simply ask her out – whoever ‘her’ is. And, if she’s not the one, you can just move on quicker.