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robeenp comments on 2015 Repository Reruns - Boring Advice Repository - Less Wrong Discussion
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Don't use it for people you care about. I've wrecked a potential date because he found out I've used Boomerang to fake indifference. It’s quite easy to figure out the email was sent through Boomerang and even how much delay youset. It's better to be "honest" or let it cool in Drafts.
Sleeping over an important mail (or letter) is a good idea in general.