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As far as the "not telling who likes him" thing goes. Am I understanding correctly that he was told that some coworker asked if he was available but then somehow a code prevents revealing the rest?
If so that is just stupid high school drama making. If it is a secret, don't tell him anything. If it isn't just tell him. And then, when you do don't forget the note that says:
Cindy asked Mary to ask me to ask you if you like Margaret. Please check one:
Yes
No
Only if I'm drunk
Only if she's drunk
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