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I think the key difference between whether or not to send an email at 2am lies in how well you know the person and whether or not their judgement of your sleep cycle has a potentially negative impact on you. I wouldn't, and don't, judge 99% of people for emailing me at 2am. It does usually end with funny and bonding conversations about our weird hours. However, if someone I've never spoken to before applies for a 9-5 job emails me at 3am, I may be concerned about their ability to arrive at work on time, etc.