Most Helpful Guy
He thinks you're fun to be around but it sounds like he's testing the waters to see what you'll say... Quite a lot of guys like to know if they have a chance with you first and so they will do what they have to do to get information that would help them... even if that means trying to get you to say something they might want to hear but being suggestive in what they say.
If you're just hooking up then tell him you want something more than just a hook-up, and see how he reacts.
He won't fault you for saying what you want, and being honest with him, and if he doesn't want something more then you get to make an honest decision about where things go from there. And if he does then he's not worth your time.
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Most Helpful Girl
Like he thinks you're fun to be around