Question #1: Is it clear to everyone in the room that you feel complete goodwill toward the “target” of your sarcasm?
Solution: Avoid sarcasm where it could be misunderstood.
At its best, sarcasm and joking around can create levity in hard situations. We all need to relieve the pressure valve on life sometimes! If everyone in the room knows that we have complete, unconditional respect and care for the person we are being sarcastic with, then it is just funny.
But what if anyone in the room has doubts about that? We discovered that people are often laughing on the outside … and wondering on the inside if you really mean the sarcastic dig and if you really are that cynical, or mean, or “superior.”
If you’re not sure that people know you unconditionally care about and respect the other person, consider setting aside the sarcasm until you’re sure it isn’t acting like a pinprick to the other person’s heart.