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Let me tell you the five magic words. I agree that you ideally would feel totally comfortable asking him out, but you are not. That’s not the end of the world. So there is a half-step that you can take. It’s simple: it isn’t really asking him out, it’s just letting him know that you would say yes if he asked. So, next time you see him, deploy this weapon:

“We should hang out sometime.”

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