Dear Dr. Date,
There is a young man that I like, he is on the crew team here at the U. I used to see him quite frequently at practice, as I am on the women’s crew team. I think he is a really nice guy and have talked to him on several occasions at practice. I always had a hope that he might ask me out but we always seemed to be in a group of people whenever we talked.
One week I found some courage and had decided to ask him out. I like to think that I would have gone through with it but I didn’t see him for a couple weeks and after that I chickened out. I don’t see him very regularly any more, as we don’t practice at the same time very often. I would feel like an idiot asking him out because I really don’t know him very well. (I’m not even sure that he remembers my name.) I just think that he seems like a very nice guy and would like to get to know him better and see what happens from there. I really don’t feel comfortable asking him out but I haven’t found any other option. Is there one?
— Chicken to Ask

The only other option is to position yourself correctly and hope that he asks you out. I don’t support this option as it tends to be the wimpy way out and usually doesn’t work. The major problem is that he may very easily remain oblivious to your actions or misread them as merely friendship.
You’ve got to remember that most guys feel as uncomfortable and unsure as you do.
Right now, there are dueling urges at play. On one side is the nervous anxiety of doing the wrong thing at the wrong time in tshe wrong way. We all have to deal with this annoying anxiety, so don’t feel alone. On the other side is the drive to do something you want to do. In this particular situation, I’m always going to side with the positive, proactive decision to do that something that you want to do. Don’t let fear own you.
Yes, it could be embarrassing. Yes, he could be uninterested. And yes, it could really suck. But all that nonsense will pass and you’ll be a better, stronger person for having gone after what you want.
Since groups are intimidating to you, find a way to talk to him alone. This may take some stealthy detective work, but at some point he s going to be walking or sitting alone and that is your cue to join him. It might not be the time to ask him out, but at least you can talk to him and get things started.