A bit old to be in middle school aren't ya? ┐(・ิL_・ิ)┌ tut tut *totally judging your internet life choices*
Everyone who has ever been rejected and made to feel bad about themselves in some way will have reservations about putting themselves "out there" only to be possibly rejected or hurt again so it's not girl or guy specific.
That being said, if you know that he likes you and is too afraid to do it himself, why don't you just ask him instead? If he's still too scared to take you up on a date then he's probably not worth it. Hard as it is, try to move on.
Now, if after you try this and some time later on (maybe weeks or months) he does finally come back around, don't just "jump into his arms" because you already gave him a chance and he refused. Unless he already explained his reasons before and they sounded acceptable, you need to make sure where he's at emotionally and why he all of a sudden wants to get with you even though he rejected you in the past. Its always good to be honest and forthcoming in relationships.
Also, just because other people are dating doesn't mean you need to start dating. I'm sure you've heard it before, but most high school or younger relationships don't work out long term. In fact he huffington post wrote an article about High School Relationships stating that "only two percent of new marriages in North America are compromised of “high school sweethearts"". So if you guys end up getting together and breaking up it won't be the end of the world no matter how much it will feel like it. Accept those feelings in the moment, validate them because they are real, but learn to let them out and then let them go and move on. And ignore all of the adults who tell you your feelings aren't real because they are. Us adults just know from experience by now that dating in high school isn't worth it because most of those relationships don't work out. But if nothing else as long as the relationship doesn't negatively effect your school performance I'd say go for it. High school dating, while usually not lasting, can help you have some extra dating experience down the road so that you'll better know what you want from a relationship and what kinds of people to look out for. Personally I never dated in high school or even start of college but looking back I probably should have. Maybe I wouldn't be so socially awkward and shy if I had opened up earlier. (Just remember that relationship is NOT synonymous with sex)
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No more than a girl is afraid to ask a guy out. We all fear rejection. It's not a guys job to step up. You can't ever truly know how someone else feels, only what you feel.
If you have a crush then make a move instead of waiting for him. If it doesn't work out, at least you did something about it. Regret comes from waiting rather than acting.
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I'd say yes, I mean what are the chances that he'd succeed?
You are still in middle school and 23? Man, you are really taking your sweet time. lol
Why is your age 23?
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