Well first it sounds like he likes you already because this "playing" sounds like flirting. Ask him is he seeing anyone currently which shows that you are interested, even if you already know the answer. And if he says no, then you are open to ask him would he like to go and do something together, just you and him. Suggest a walk, the park, even the cinema, and from that you can ask him directly any question you may have about his feelings towards you and if he would like to go with you. Don't be afraid to make the first move by asking him, you don't have to wait around for him to ask!
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