Maybe you could let him know that you are interested in him without actually asking him out. Now he doesn't have to read your mind and you don't have to feel like you are being too aggressive. Say something like, "Wow, it's been so nice getting to see you so often lately. I'd really like it if we could see each other more." You're being honest and open and allowing him the chance to choose how he wants to recipricate. Trust your gut!
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