I am 16. There's this guy I'm startig to like and it's been about 8 months since my boyfriend of 2 years broke up with me and I'm really happy I've found someone new that I'm into. I want to know if he may be interested and how I should pursue him... First of all, a couple times a week, we talk to each other online till really late, recently it's been as late as 3:30AM. After school a lot of the people at my school like to hangout in the front of school to socialize for a few minutes and according to my friends, he's always staring at me from afar when he's with his friends. Another thing is that he does little things like calling me cute , etc. next, one time I was walking by him and his friend and as I was approaching, his friend nudged him and uttered, "look it's, ______" . Another thing that's happened is that one time he tried sitting in a seat next to me in our history class but his friend stole the seat to talk to me about something and the guy a like said, "why are you trying to steal her from me?" We've also gone out for lunch a couple of times and has treated me once even. We've been talking a lot more in person and I've been trying to talk to him more. I want to drop some hints that I like him but I don't know how and I don't even know if he likes me a little

It sounds like he likes you. You could drop some hints, or just come out and bring the subject up. You could ask something like, "So, we've been spending a lot of time talking and hanging out, and I was just wondering where you're at with our friendship or relationship or whatever you want to call it. I've been wondering what you think about me but have been affraid to ask."

I think he's given enough positive signals that it would be OK to just ask him. He's probably afraid of rejection, so hasn't had the nerve to be more clear about wanting to date you. When he picked up the tab though, I think he was sending a sign that he wants to get out of the friend lane with you and be your boyfriend.

Don't be in hurry, your just 16. If he likes you let him approach you. Don't run on him. He will talk to you himself.

You're chatting a lot, if he didn't like you I doubt he would be talking to you till all hours of the morning. Just keep talking and let what will happen happen or just tell him you like him and would he like to go out sometime.