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20 tips on how to have difficult conversations (and still keep your sense of humor)



  1. First and foremost, prepare yourself mentally for the conversation. This includes a good night's sleep, and a positive attitude (or at least pretending to have one).

  2. Make sure the timing is right. Don't have a difficult conversation when the other person is in the middle of a deadline or just finished running a marathon.

  3. Choose your location wisely. If you're having a conversation about sensitive subjects, it's best to avoid having it in public places like a busy restaurant or a crowded park.

  4. Start the conversation with a joke. It'll lighten the mood and make both of you feel more relaxed. Just make sure the joke isn't about the topic you're about to discuss.

  5. Avoid using sarcasm. It's the lowest form of wit and can easily be misinterpreted. Instead, use irony, which is a much more sophisticated form of humor.

  6. Be honest, but avoid being blunt. If you're going to tell someone that their shirt is ugly, do it in a polite and humorous way.

  7. Use props. If you're having a conversation about something boring, bring props to keep the conversation interesting. For example, if you're talking about financial planning, bring a piggy bank to the conversation.

  8. Take breaks. If the conversation is getting too intense, take a break and do something silly together, like making silly faces or having a dance party.

  9. Make fun of yourself. If you're the one initiating the difficult conversation, make a joke about yourself. It'll show the other person that you're not taking the situation too seriously and that you're willing to laugh at yourself.

  10. Use gestures. Use exaggerated gestures to make your point and keep the conversation lighthearted.

  11. Sing. If the conversation is getting too serious, break out into song. It's a great way to diffuse tension and bring a smile to both of your faces.

  12. Use analogies. If you're having a difficult time explaining something, use analogies to make your point. For example, instead of saying, "I'm feeling overwhelmed," you could say, "I feel like a hamster on a wheel."

  13. Use humor to diffuse tense situations. If the conversation is getting heated, use humor to diffuse the situation. For example, if the other person is getting angry, make a silly face to lighten the mood.

  14. Use humor to express empathy. If the other person is upset, use humor to show that you understand and care about their feelings.

  15. Make fun of the situation, not the person. If the situation is frustrating, make a joke about the situation, not the person. For example, instead of saying, "You're so forgetful," you could say, "I think we need to install GPS in your brain."

  16. Use non-verbal cues. Use facial expressions, body language, and tone of voice to communicate that you're not taking the situation too seriously.

  17. End the conversation on a positive note. Make a joke or use humor to diffuse any lingering tension and end the conversation on a positive note.

  18. Follow up with a joke. After the conversation, send the other person a funny text or meme to show that there are no hard feelings.

  19. Practice makes perfect. The more you have difficult conversations, the better you'll get at using humor to make them less difficult.

  20. Lastly, remember that laughter is the best medicine.

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