I never had any issues. I learned early on that the pretty girls got asked out the least. I didnt ask many out though cause I didnt have time for all that. Most of my freinds were an still are girls an what little free time I had was spent with them. Over half of them told me later that they had a thing for me. That never crossed my mind back then though.
I had it easy back then though. I was expected to be the aggressor an girls were expected to take that as a compliment even if they were not interested. I remember the first time a girl approached me vividly. I was in college at the time. I was spending more time in the city an was killing time at the mall. Girl bumped in to me twice in a radio shack then started talking to me about TVs. I was being nice an talking to her but it never crossed my mind what I now know was going on. I Just assumed the chick was clumsy cause girls didnt do that where I was from. I bet she left that store lost as to why this dumb country boy didnt get her hints...
But like I said, I had it easy. Any guy in the school could ask out any girl in the school know that the worst thing that would happen is to be politely declined. Girls today make a scene if they are hit on by someone they dont want to go out with. It can be downright rude an very public. Things have changes big time in the last 10 years. I got to watch the change an get use to it, even learning how to handle the rude responses. The kids I mentored though, that is their life. They have watched others get shot down hard an dont want to take the chance. The effect of that is that most girls are not being asked out by anyone anymore, many of which thinking something is wrong with them. You also have a rise in guys hitting on girls is a rude an sarcastic way. I think that is also cause by fear of rejection.