Managing Both Responses

(My roommate works for a frame shop. A mutual friend of ours was the store manager and would frequently complain about how stressful it was. She soon quit. I’m in the store browsing for art supplies when I run into my roommate.)

Roommate: “Hey, guess what? With [Our Friend] quitting, they’re promoting me to store manager.”

Me: “Oh! Congratulations… or my condolences? I’m not sure what’s the appropriate response.”

Roommate: “Probably both.”

(It wasn’t long before he left too.)