Sometimes on a date, it can be hard to think of meaningful questions in the moment. I decided to compile a list of dating conversation topics to help myself out, and it ended up becoming such a fun writing exercise. (I did a lot of this on the beach.) So, here it is…conversation topics to help you get to know your date better. Please add suggestions to help us all out, and please share this list with anyone who might find it helpful. I update this list periodically.
When asking questions,it’s a good idea to try and weave them into the conversation instead of doing this interview-style (unless you both agree that you would like to do that).
Relationships and Mentors:
Who are the most important people in your life now?
What is your relationship like with your mother? With your father? Siblings? Are you comfortable with these relationships as they currently are?
What do you look for in a friend?
Were/are you close with any of your friends’ parents? Older relatives? Former teachers?
Do you have a role model? Or any role model families? What do you admire in them?
Who do you talk to when you need to get clarity on something?
Goals, Strengths, and Outlook:
If you could devote yourself to solving one of society’s/our community’s problems, what would it be?
What do you think is our generation’s greatest strength and greatest challenge?
How would you spend your time, money no object?
What do you think is your greatest strength you can contribute to a family? To a community?
If you won the lottery, where would you give charity?
What is your attitude/have you given thought to financial matters like lifestyle, budgeting, credit card use, long-term financial goals, etc.? (obviously a loaded topic, but one that should be discussed when you’re talking seriously about other matters)
Future Family:
How important is it to you for your family to spend time together? To eat meals together? To go on family vacations? To visit extended family?
How important is it for a couple to spend time together? For parents to spend time with individual children?
How important do you feel it is for a mother to be home with her children?
What do you think the role of a mother and of a father is in a family?
Do you think about what your parenting will be like? Do you do anything to prepare to be parent (i.e. reading, observing, talking to relatives or mentors about parenting)?
How comfortable are you around young children? How easily do you relate to them? (There is no right or wrong answer to this).
How do you envision your family’s Shabbos and Yom Tov table?
Describe the feeling you want people to have when they walk into your home.
What are the most important values and lessons you want to give over to your children?
How do you want to celebrate birthdays, anniversaries, and other special events?
Do you enjoy or need to spend time alone?
Spiritual Life:
What do you most enjoy in learning/what is your favorite kind of learning?
Are you working on anything specific now?
If you could correct a flaw in yourself, what would it be?
What are your best/most uplifting/funniest memories from your time in Eretz Yisroel (if you went)? Anything you’d rather forget? Is there anything you saw or experienced in Eretz Yisroel that changed how you live or that you want to carry over into your future home?
What is your favorite minhag? Why?
What is your favorite Yom Tov? Why?
Do you have personal minhagim that you want to incorporate into your celebration of the Yomim Tovim?
Childhood and Family:
What was high school like for you?
What was your favorite family vacation?
What was your favorite childhood book?
How important were/are birthdays in your family?
How did your family celebrate bas mitzvahs?
How often does your extended family get together? Are they expected to show up to all simchas?
What is your earliest memory?
What was your favorite subject in school?
What was your level of independence growing up?
Did you make any promises to yourself as a child about things you would or wouldn’t do as an adult? (this can be funny or serious)
Did you have a favorite relative to spend time with when you were a child?
When did you first realize you were growing up?
Did you have a best friend?
What did you want to be when you grew up?
What would you change about your childhood?
Difficult memory? Happy memory?
What were your struggles as a child and have you overcome them? What helped?
The Fun Stuff:
What are you really good at?
What is your ideal vacation?
What is your favorite place in the world?
What is on your bucket list?
What’s in your dream home?
What’s a skill you would enjoy learning, given enough time?
What’s something you want to try, even if it isn’t something you’d be particularly good at?
Do you like to cook or bake?
Do you like to eat out? What’s your favorite type of restaurant/cuisine?
Have you ever taken a personality test? What were the results and do you agree with them?
Have you read anything good lately?
Did you memorize anything as a child that you still draw on today?
Do you or did you collect anything?
Do you follow politics/the news? How strongly do you feel about your political views?
What was the best gift you ever received?
P.S. Check out recommended dating books.
