"Teaching Bad Apples" is a game developed in 2014 for current and future teachers. It plays much like "Apples to Apples" or "Cards Against Humanity," with each player in turn reading a situation card, followed by the other players choosing their response cards. Each situation, however dramatic or bizarre, is authentic, obtained through crowdsourcing, social media, and online teacher forums. After many playtests, including feedback from practicing teachers and teacher educators, we concluded that the most effective way to teach people to deal with these dicey situations is to have players provide wildly inappropriate responses to the authentic situations, and then in the debriefing talk about "what you would really do." Effectively the game teaches by counterexample, and by making light of these situations it breaks down conversation barriers and then gets into authentic and appropriate reactions. This game format lends itself to teaching content in a variety of areas where dealing with difficult situations is important.