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Should I ask him out?

Anonymous
This guy and I have known each other for a long time. I work for his mom as her assistant. We have hung out a couple of times, but never in a romantic setting. He has messaged me a few times around 10 pm-ish saying "Hey". But I have always been asleep and have not seen his messages until the morning and then I don't reply because I think that might be weird. Should I text him? We do flirt whenever we see each other. I just don't want to embarrass myself.
Should I ask him out?
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