Get your girlfriend talking about positive things—the memories that give her all the good feelings and make her smile.
1. What is your most treasured memory?
2. How have your parents impacted your view of love and relationships?
Did she grow up in a secure family environment? Don’t probe too deeply on this one if she seems closed to sharing.
3. What are some of the cultural pressures that people put on you as a woman?
Just like the pressures and expectations you face, there’s a fine line that people expect a woman to walk. How is that impacting her?
4. What question have you wanted to ask me?
Maybe she wants to know if you’re married with 12 kids, but asking feels awkward, and she doesn’t want you to be offended.
5. What are your 5 travel essentials?
What does she value so much she can’t live without? Ask follow-up questions to spark further conversation and dig deeper into her values.
6. What was the best gift you’ve given someone else?
If she’s thoughtful and unlikely to brag on herself, this question shows you a part of her she might keep quiet. You’ll also learn about how she thinks.
7. What was your favorite book in high school? What’s your favorite book now?
This is a fun question that can lead to conversations on what she was like in high school and how she’s changed over the years.
8. What are your physical boundaries?
This is a great question to ask early in the relationship, so you’re both on the same page.
9. What was your favorite breakfast cereal as a kid?
You can learn much about her background from this fun and innocuous question. If all you discover is a shared obsession with Cocoa Puffs, this question is a warm and fuzzy dose of nostalgia.
10. What do you believe about life after death?
Do you have compatible spiritual views? Find out the answer to this question early on, and explore how important it is to be consistent in this area.
11. What do you wish a guy would ask you but never has?
If you want her to feel attracted to you, give her control of the conversation.
12. What do you wish people knew about you?
Give her a chance to share who she is and that you want to see the real her.
13. What gets you out of bed every morning?
Learn about her passions and what gives her purpose every day. You may also find out about responsibilities you didn’t know she had. Maybe she has a child she didn’t tell you about yet, or she lives with her sister and helps take care of her nephew.
14. What signs can I look for to know when you aren’t ok?
You know you’ve hit the danger zone when your girlfriend says, “I’m fine,” or, “It doesn’t matter.” Or even worse, the wall of silence.
15. What do you like most about yourself?
It’s good to know how she views herself, and you can even build her up in the areas she feels strongest.
16. Can we talk about our health histories?
It’s never comfortable to ask someone if they have mental or physical concerns, but when you’re in a relationship, it’s essential to know what your SO is struggling with.
17. If you’re angry, what do you do?
If she doesn’t see this as a problem or even thinks it’s funny, you’re looking at a relationship that could turn toxic very quickly.
18. What are your political views and ideals?
If you’re starting to get serious, do a values check. Do you have similar political views, and if not, are you comfortable with that? If it’s not a dealbreaker, talk about how you can hold differing views and still be respectful of the other person.
19. What do other people do that frustrates you?
Learn how she handles stress and what her pet peeves are. If you know her frustrations, you can avoid annoying her.
20. What are your favorite things to do?
It sounds like a simple question, but it gives you important information. Ask this early (even on the first date) to find out what you have in common.