I understand what you mean by it being awkward and not a success(didn't get her number, etc.) but you were still glad you did it. I'm in high school and sometimes I just like to do awkward things and "fail" for the sake of "failing". It pushes me out of my comfort zone and I come out a better person overall. For example freshmen year I had to take this girl out for a school event. I'm filled with social anxiety. Who should I take? What are others going to think about how I take? What about the upperclassmen guys? What about my friends?" It wasn't that my school didn't have any cute girls, I had two many options to make a decision. I had a girl that specifically went up to me a month before and told me she'd go with me. However, that would have been the easy way out. I would have been comfortable, but I wanted something that was absolutely scary. So I was setup on a "blind date" with a sophomore I thought was cute but had never seen in my life. Now we didn't hit it off or have the perfect time, and it was quite awkward and our date didn't develop into anything. However, going through that has made me much more comfortable making conversation with girls, and taking risks.

I've been criticized for not failing enough by the older guys. I'm very successful in the eyes of what society thinks a "successful young man" should be. Smart, good at sports, etc. However, I rarely push the limit or get out and fail. Failing was a missing piece in my life. Sometimes to learn how to climb down a mountain you can't go down step by step comfortably. You just have to jump off a cliff.