He’s someone who I know we’ve actually hooked up once before in the past. I don’t know why it’s complicated to tell him to call me when he’s single.
Unless you have a reason to believe he is not single, it sounds like you are assuming the worst and trying to prevent issues you may not have. Imho it is best to approach things with a positive mindset expecting things to go well, until proven otherwise by his rejection.Maybe I am biased because last time someone told me to let her know when I'm single, it took a year and a half and she herself was not single anymore by then. It sounds like you think more about reasons for possible failure that about the hope of success.
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