Dear Val Helpless,

I think real issue here is not who you should you ask out, but why you feel you need a boyfriend?

I think you have very low self esteem issues. That's why you feel you need to ask someone out.

In each of the boy scenarios you second guess yourself. Just because this kid is popular, why do you think he would not like you. Obviously you do not have a lot of faith in yourself.

I think also that you like the bad boys because you mention that the first guy is too sweet for you. I do not know how your relationships in the past have been but people who shy away from nice guys are turned off for that reason, they are too nice.

I understand that situation because I am the same way, I can't stand when guys are too nice but hate it when they are mean.

My advice to you would be work on liking yourself first before you pick someone to like you as well.

– Valetta