Deep Conversations Dating Couples Can Have

Although you probably should not use these deep conversation starters for a first date, they work well to find out more about a person. The answers can reveal some hidden facts and lead to a deeper relationship. Pick carefully, however, as some may mean the end of a beautiful relationship.

• Talk about a significant event that caused a positive change in you as a person.
• Talk about your future; how you picture your life in five years and in ten.
• Who is your hero and what qualities make them your choice?
• Tell about a time when someone showed you kindness or compassion. Tell about a time when you showed compassion or kindness to someone else.
• If you won the lottery, what is the first thing you would buy? Why?
• Find similarities and differences. Discuss them.
• What makes you excited? What was the last exciting experience you had?
• What is your favorite item of clothing and why is it your favorite?
• What values are important in your life? Were they imparted to you by your parents? If not, from where did they come?
• What kind of date do you consider romantic? Plan a romantic date night together.
• What scares you the most? Has what you are afraid of changed since you were a child?
• Discuss your first impression of each other and whether it was accurate.
• Has your relationship changed since you began dating? Give some examples to support your answer.
• What would cause you to end a relationship? Would you be able to forgive and forget and renew the relationship?
• Have you ever had a very bad nightmare? What was it about?
• When and where do you feel most like your real self? Why?
• Which celebrity is your favorite? What do you find attractive about them?
• What characteristics do you think are necessary for a strong relationship? Do you possess these characteristics?
• What controversial issue – social or political – do you feel strongly about? Why?
• What was your favorite book as a child? Why was it your favorite?
• What was your favorite movie as a child? Do you still enjoy seeing it? How many times have you seen it?
• If you could go back to your childhood, what advice would you like to have from your adult self?
• Share a secret about yourself.
• What would you do on a “perfect” day? Would you want to do something with someone else or be alone?
• What is one thing that scares you the most? Why?
• If you could be any character in a book or movie, who would you be? Why?
• Describe your biggest regret?
• What did you dream of being when you were a child? Have you managed to achieve any of your dreams?
• What is your dream job and do you believe you will ever succeed at having it?
• How many siblings do you have and are they older or younger? How is your relationship with them?
• Tell about a time when someone hurt or betrayed you and how the experience has affected your adult life.
• Tell about your most difficult challenge thus far in your life. Were you able to overcome and what did you learn?
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