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Does he try to spend more time with you than any of his other female friends? Does he seem interested in what you say unlike some other boys? Does he act differently towards you (in a nice way) than other girls?
And it will depend on the age, maturity of the boy and the culture the boy is raised in. He may ignore you completely, he may stare, also at times girls mature and get an interest in boys before the boys have the same in girls. Often if one is too scared to talk to the other, there is little you can do
If he really likes you he will most likely tell you. If he's extremely shy when it comes to asking girls out, he should be exposing certain clues. He'll stare at you, or he'll act differently when he's around you. Or, he'll constantly tease you, or he'll always want to know how you're doing, or he'll want to get your attention.
Do you flirt with him? Does he respond?
Try flirting with him in a more obvious way, then he'll be more comfortable to show you his feelings if he likes you.
Compliment him, tease him, this can let it out of him.
If it doesn't, then either he doesn't have feelings for you, or he's afraid to show it. There may be another reason, but you can never truly know until you ask him directly.
Try asking him, if there were anyone he would date among [a group you're included in] who would it be?
Don't be afraid to approach him about the subject. Think about what the worst possible scenario would be. Then the best possible scenario. Which is most likely to happen? And are you willing to take a chance for the best to happen? Then take a chance and just do it!
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