38 Interesting Questions To Ask Your Mom Right Now

A year and a half ago, my mom , my sister and I met up for dinner at a cozy Italian restaurant in New York City with two of my aunts and my aunt’s longtime best friend. 

Over a couple glasses of wine, my mom, her two older sisters and our family friend who all lived, worked and partied in Manhattan in the 1980s spent the evening reminiscing about their apartments, jobs, relationships and other escapades at the time.

I learned a couple of things about my mom that night for example, in her early 20s, she dated a very wealthy man in another state who used to fly her back and forth on his private plane that I’d somehow never known or ever thought to ask about. It was another reminder that before she was my mom, she was a person with her own life and set of experiences that had nothing to do with me or my siblings.  

Over the years, you might slowly pick up bits and pieces of your mom’s life story, little breadcrumbs she drops here and there. But for many kids, myself included, the focus has almost always been on us not our parents since the day we were born.

Below is a list of things you may not have asked your mom , but should. The answers to these questions will help you know her more deeply and hopefully give you a better sense of her past, her life experiences and who she really is. 

Here are 38 conversation-starting questions to ask your mom right now: 

1. What’s one of your earliest memories?

2. What’s the most trouble you’ve ever gotten in?

3. What was your relationship with your own parents like?

4. What’s something you always wanted to do but didn’t and why didn’t you?

5. Was there something your parents did when you were a kid that you swore you’d never do yourself?

6. How many serious relationships were you in before you settled down (if you did)? What were they like?

7. What was your hardest breakup like?

8. Growing up, what did you think you wanted to do for a living?

9. How have your notions of what it means to be a woman changed over your lifetime?

10. (If she worked): What was it like being a working mom at that time? Would you do it all over again? What would you change?

11. (If she didn’t work): What was it like being a stay-at-home mom at that time? Would you do it all over again? What would you change?

12. When did you lose your virginity and to whom?

13. Who were/are your role models? Who did you look up to when you were younger? Who do you look up to now?

14. What’s the best trip you’ve ever taken?

15. Who was your best friend growing up? Who is your best friend now?

16. Have you ever had an abortion?

17. Is there a moment or event that radically changed the way you saw the world? 

18. Have you ever done something really impulsive? How did it go?

19. What was the moment I hurt you the most when I was growing up?

20. What was the moment I frustrated you most when I was growing up?

21. (If she got married): When did you know that you were ready to get married?

22. When did you know you were ready to have kids?

23. What do I need to know about our family’s medical history that could affect my health or life?

24. What was the day I was born (or adopted ) like?

25. (If she got married): What was your wedding day like?

26. What’s the worst fight you ever had with my dad?

27. What’s your favorite photo of yourself? Of our family?

28. What was the first year of motherhood like for you?

29. What do you want or wish most for your kids?

30. What do you want your funeral to be like?

31. What was life like for you at my age? 

32. What were some of your biggest struggles or insecurities in high school?

33. Were you ever sexually harassed or sexually assaulted?

34. Do you have any health issues you’ve never told me about?

35. What would your perfect day be like? Describe it. 

36. What’s the one song or album that means the most to you? 

37. Is the present year anything like you imagined it would be when you were growing up?

38. What advice would you give to your younger self at age 20? 30? 40?