Dear Urban Diplomat: How do I tell my best friend that his on-court tantrums won’t fly at my tennis club?

Since you’re his best friend, it falls to you to dish out some Dr. Phil–calibre emotional honesty. Tell him you’re worried his antics might reflect poorly on you. He might understand and dial down the racquet-smashing routine. If you fear he’ll Hulk out on you, there’s always the less lion-hearted approach: invite him to apply, say you’ll do your best, mumble something about a “blasted new review board” and direct the form to the circular file. After a few weeks without response, he’ll take the hint or lose interest, leaving you with your best friend and your job.

Send your questions to the Urban Diplomat at urbandiplomat@torontolife.com