Try just breaking the ice every time your with him or trying to talk to him, make jokes about things you both heard about, ask him what he thinks about things and try to invite him to do things with you if thats allowed. like to poster before me said, you didnt give us your age so im not sure how to help guide you here.
Dragonflymagic answered Monday December 22 2014, 9:09 pm: Is it that you have a problem with the fact that he is shy or that he texts your girlfriend on FB? Or are you interested in him at all, or not? You didn't give an age. Depending on your age, the parents may have some guidelines and rules for you on dating. So the possibilities of what I could suggest are quite a few.
If you parents won't let you date til 15,16 and you are 13, 14, then let him know that your parents won't let you officially date yet but you do like him and want to spend time with him. Then ask the parents if a friend who is a boy can come over to hang out while they're home. Some parents, (me included) are more comfortable with something supervised by them loosely, with the boy visiting at your house.
If you don't like that he is texting a friend and not you, then ask him why he texts your girlfriend and doesnt text you but wants to ask you out. He may have a perfectly good explanation. Then decide to accept or not.
If you are an introvert and very talkative and he being shy, you don't feel you'd have enough in common, then say so, "Um Josh, I know you're kinda shy and I am very outgoing? Since I really don't know you well except for that one fact, I'm not sure we'd have anything in common. So I am not sure about accepting to date unless I knew a little more about you. Would you be willing to talk with me for some time first or at least on FB/or other social site first?
If it doesnt matter whether he is shy or talks to your girlfriend, and there's no restrictions on dating, then tell him, you'd love to go out with him and suggest some places that you would like to go together, whether hanging out at the mall, at a fast food place or your house or his. [ Dragonflymagic's advice column | Ask Dragonflymagic A Question ]
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