Casually approach him and strike up a small conversation.,
Get in contact with him on a social network.,
Attempt to talk to him a few times a week.,
Gauge his feelings and drop hints that you like him.,
Make physical contact after awhile, but be sure he’s okay with it.,
Ask him out.,
Keep the date simple if he agrees.,
Every person has an ego.,
Let him feel competent by having him help you with something.,
Be genuinely interested in him.,
Be approachable and attractive, but not so stunning and loud as to draw him away.,
Throw a small party and invite a few people you know he’ll be comfortable with.
Remember, shy people are just like everyone else except with a wall, like I said; they won’t run away if you make quick movements. Small conversation is usually rather impersonal and can consist of: the homework, weather, teachers, something on the news, or otherwise. If he really likes you, he won’t be able to stop thinking about you.
If you don’t go to school with him, maybe ask what he likes to do other then homework, and school, or even maybe ask for his number. Remember if he doesn’t text you first don’t sweat it. If he’s shy in person with you, he’ll be shy everywhere with you!;
, It won’t intimidate him as much, and will give him a chance to think about his answer. If you don’t have social media, just try asking for a simple number.
, By talking to him a few times a week, you will begin establishing a bond and he may start to tear down his wall for you. After small talk, you should begin moving onto personal things like: family, travel, summer vacation plans, his hobbies, and other casual but personal topics.
, After you’ve talked to him for awhile, transition conversations onto a more personal level. Perhaps talk about what you both are looking for in a person, and drop hints that what you’re looking for is him.
, Don’t ask him if he’s okay with being touched, just do it once and see how he reacts. A touch or pat on the shoulder is fine. If he seems to dislike it, then refrain from touching him until you know he is more comfortable with you. However, if he seems fine with it, then you should continue to do it every once in a while. Don’t go too far; hugs (when needed), small touches on his arm, and pats on the shoulder are just fine.
, Make sure to do this in private and one-on-one. Don’t even ask around close friends, or else he might feel uncomfortable as well as feel pressured to say yes. You want him to say yes because he wants to, not because he thinks he needs to. He might also be pressured to say no, so be careful.
, Going out to public places is most likely not his thing. Suggest a movie at your house (though he might be afraid to meet your parents) or something else that’s away from people. You could also suggest getting drive-through dinner and parking some place quiet to eat and talk.
, If necessary, find a way to increase his self-esteem. Make him feel confident around you.
, It could be a homework problem or where to buy the latest gadget. Whatever works.
, Because shy guys are guys too! Find out his hobbies or passions. Or talk about a common interest. DO NOT PRETEND TO LIKE SOMETHING YOU DON’T! But ask open-ended questions about it. It will make you a good listener, get to know him better, and you will have fewer chances to say something stupid. (If you do anyway, as 99% of us do, forgive yourself.)
, Most guys actually approach cute girls over gorgeous girls because they find really pretty girls out of their league. This applies particularly to shy guys, who have little confidence to begin with. I’m not saying it isn’t okay to be really, really, really, incredibly good-looking. But don’t draw so much attention to it. Now is not the time to try cutting-edge fashion or over-the-top makeup.
, Make it fun by trying some ice-breaking games and whatnot.