Please help!!

You ask him to go to some place with you with some friends, try starting with a school game or something, then as he gets to know you, lessen the group. So start with a huge group thing like a football game, then go to hanging out with you and a couple friends on both sides, then if he begins to like you, ask him to go out together on a date. If it goes well, go on a few more.

OR you could just go up to him and say "Hey, do you wanna go out with me?" but if he barely knows you exist, well that may not be the best thing.

May I ask how old you are?

Before you even think of this, you need to get your parent's permission. If he is 14, that means you are around the same age, possibly younger. Which means your parents may not be too happy about your starting to date.

As Lyra said, if its OK with your parents see if you know someone in his group and start hanging with them. So he can get to know you.

ScottGem, I assumed the parents had given permission, as many parents these days are giving children as young as 11 permission to date.

I should have mentioned the permission issue though, good thing that you did.

ScottGem, I assumed the parents had given permission, as many parents these days are giving children as young as 11 permission to date.

I should have mentioned the permission issue though, good thing that you did.

I don't think we can make such an assumption. And it disgusts me that parents would let children that young date.

Good point. I do know what assume makes out of u and me! My mistake. And it is disgusting. I know of a girl who is now 15 but at the time she was 12 and dating and also on birth control because she was "active"