By saying he has a crush on you he practically says he wants to date you.
Two options
He just doest know how it works, if that's the case you could ask him out(no way he says no).
Or he doesn't want to go on a "official date" because He's scared things might get awkward and he just wants to have a fun time with you.
So, you're in a pretty good position.
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This is like a rule
If a guy says he will pay, you should object. If he insist, let him pay, he is happy to. If he just says OK and agrees with you, you should split, never pay for the whole thing if he asked to pay for it before.
So if he insisted you shouldn't feel guilty.
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