As much as archer86 has some great insight on feminism and etiquette in the workplace, I think you need an answer from someone a little closer to your own age and who is in-tune with the teen dating scene.
What you have to do is see how he reacts when you address him directly. If he gives you a straight answer with little emotion, then he is either EXTREMELY shy, or doesn't like you, either way it won't work out. If you see him light up a little or he seems like he's trying too hard to answer simple questions, then he is just shy but you probably have to make the first move. Also, take into consideration how he acts around other girls.
Depends on the situation. Sometimes, I avoid woman's eyes completely in public because as an average looking man, I get the snobbish looks as though my eyes upon them ruins their divinity. At work, I don't do anything or say anything around women unless it is directly focused on the task at hand, so that I don't get fired for harassment. I don't approach women at all anymore, have no idea how negatively they will react. I don't do much with teens, somebody may think I'm being a dirty old pervert who will try to have sex with underage girls. In addition, there is the feminist men-hating mentality that is so open in our society. As you can see, some men are consciously giving women all the space they could possibly want. Not your fault, 16 years of men bashing has damaged our country far worse than 9/11. That is realism.
Um yeah. Well this guy is only 15 and really good looking - 6 months ago
Answerer
Makes very little difference. If my 14 year old cousin can get kicked out of middle school for looking at a girls chest, any male can get into trouble just for being a male. It may not be so for you younger folks but it's still out there. Most boys your age are either shy with girls they like or come on too strong. I say take the initiative and go to him, make it clear it is ok for him to come on to you. - 6 months ago