25 Stimulating Deep Relationship Questions

Couple talking

When deep conversation ensues as the result of a question, partners learn more about each other and grow closer. These questions are designed to prompt conversations yielding poignant conversations that reveal the true nature of a person.

Revealing Questions

These questions are designed to prompt further discussion, revealing more about your partner's character and how they think.

  • Who do you most admire, and why?
  • Did you enjoy your childhood?
  • If you had a million dollars to give to a charity, which charity would the money go to?
  • Do you think men and women are equals?
  • What is your biggest fear?
  • What makes you angry?
  • What do you need to feel fulfilled in life?
  • Do you think people are more influenced by their environment or by their biological traits?
  • What do you think your purpose is?
  • Who is the villain in your life story?
  • What words do you think people use to describe you?
  • What words do you want people to use to describe you?
  • If you could change one thing about yourself, what would it be?
  • When was the last time you cried?
  • Do you think Younger You would be happy with what you have become?
  • What is the best way I can be a supportive partner to you?
  • What has been your greatest accomplishment in life thus far?
  • What has been the happiest moment of your life up until now?
  • Are there things I say or do that make you want to spend less time with me?
  • For what do you want to be remembered?
  • How can I make you feel more appreciated and honored?
  • What do you think we can do to make our relationship stronger?
  • Do you think we are all at the mercy of fate?
  • When do you feel most loved?
  • If I could live your life for one day, what do you think would surprise me the most?

Prolonging the Talk

The more information you can pull from your partner, the more you will know about him or her by the time the conversation ends. Ask open-ended questions, and if your partner responds with a simple, one-word answer, follow up with more questions to lead your partner toward elaborating. Don't prod your partner if a topic seems to be painful. Be understanding as there may be things that are difficult to talk about. You can keep the conversation going with even more suggestions for would you rather questions for couples and deep questions to ask your girlfriend or boyfriend.

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25 Stimulating Deep Relationship Questions