Sometimes on a date, I find myself drawing a blank. I’d really love to ask questions that aren’t too intense but go a bit deeper than “What do you do in your free time?” 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 thinking about this on the beach.) So, here it is…a list of conversation topics to help you get to know your date better. Please feel free to add suggestions in the comments below and help us all out. And please share this list with anyone who might find it helpful!
Childhood and Family:
What is your earliest memory?
What was your favorite subject in school?
What was your favorite summer vacation?
Did your family do road trips/long car rides? What are you memories of those?
What was your favorite childhood book?
How important were/are birthdays in your family and to you as an adult?
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 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?
Did you have or want a pet?
What did you want to be when you grew up?
Relationships and Mentors:
Were/are you close with any of your friends’ parents? How about any older relatives? Former teachers?
Do you have a role model? Or any role model families? What do you admire in them?
Goals and Strengths:
If you could devote yourself to solving one of society’s/our community’s problems, what would it be?
If money weren’t an object, how would you spend your time?
What’s a skill you’d want to learn, given enough time?
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 your maaser?
Do you have any personal traditions – for celebrating birthdays, milestones, Yomim Tovim?
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?
Do you think about the kind of parent you’ll be? Does that have any practical implications in your life now (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?
What are your best/most uplifting/funniest memories from your time in Eretz Yisroel? 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?
Do you have a favorite minhag? Favorite perek of Tehillim or tefillah? Favorite part of Tanach? Favorite Yom Tov?
What do you most enjoy in learning?
If you could correct a flaw in yourself, what would it be?
The Fun Stuff:
What are you really good at?
What would your ideal vacation be?
Do you have a travel bucket list and if so, what’s on it?
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?
Do you enjoy spending time alone?
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’s something new you’d want to try, even if it isn’t something you’d be particularly good at?
What was the best gift you ever received?
P.S. Check out recommended dating books.