Based on all the things you said happened between you two... I would suggest that you go ahead and take a chance and discuss your feelings with him, and discuss his feelings as well. Another suggestion to go with that is that you find a good time to discuss it with him, but in person, and away from your friends. It may go either way, but don't wait too long, cause it may be too late later on and he may fall for someone else. (the last sentence comes from my personal experience.) I hope that my answer helps =)
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