Everyone is saying you’re doomed but I think it’s salvageable as long as you are very good at setting boundaries and keeping to them.

Do not encourage his oversharing, do not offer too much advice as that will only draw you in. Do not allow anything that would overstep the line, this includes him saying things like “You’re his type”.

If he says something like that again the simplest non-confrontational response is something humorous that clearly points out the line he’s trying to cross.

Something like “Well that’s awkward…” Or “What a strange thing to say…” “Yeah that’s way over my pay grade…” Say it jokingly and laugh, so things stay friendly, but you have pointed out the line instead of your nervous laughter sounding like agreement.

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I love this! Cheeky cross stitch is the best!