1. What's the silliest habit you have?
This is the kind of question that will make her laugh while answering. Who wouldn’t laugh talking about their silly habits? But make sure she feels open enough to share with you. If not, the conversation might feel awkward and go nowhere. On the other hand, if she’s willing to open up, the chat will definitely become warmer after that.
2. If you had to choose between love and money, which one would you pick?
This question is a bit of a test. Of course, no girl will directly say she would pick money. If you get an answer like that, it means you’ve become a close friend to her. When asking this, I want you to make a slight evaluation (not everything) about the issue. Generally, women will respond with a balanced answer, something like 'Of course I would choose the one I love, but money is also necessary to live' or 'Money is important, but love is crucial.' So, you’ll need to be sharp and pay attention to her words, tone, and expressions to figure out which she values more. However, women do enjoy answering these 'either/or' questions.
3. What did you think of me when we first met? Did I seem okay?
This question is meant to have her describe her first impression of you. If she likes you, her response will be very interesting, and you’ll get a clear idea of what she thinks about you. On the other hand, if she wasn’t that interested, she won’t have much to say. At that point, you can easily guess her answer, as it might be a generic response you’ve heard before.
4. If I suddenly kissed you, would you slap me?
This is a fun question, but only if you and she are chatting naturally and comfortably. Trust me, it works because it makes her imagine your kiss. Waiting for something unexpected is thrilling and nervous, and with this question, you’ll put her in that exact state.
5. Are you feeling lonely tonight?
This is the kind of question I often use to invite someone out. It's a question I can almost predict the answer to: 'Okay, let's go out tonight. I’ll make sure you’re not lonely.'
6. What are the top 3 things you wish to do right now?
This is a general question for a variety of things, and it gives her the chance to share some of her deepest wishes. It’s also a perfect opportunity for you to show your thoughtfulness. After her little whispers, there’s sure to be something you can help her with.
7. If you could go back in time, what’s one thing you’d change?
Regret is one of the most negative emotions. With this question, you'll learn what she values most and has lost. This brings both of you closer, and makes you appreciate what you have together even more.
8. If I ever hurt you, would you let me know?
Women often hide their emotions, but if you encourage her to open up with questions like this, she’ll feel both loved and listened to. That means a lot to her. And by doing so, when you make a mistake, she won’t keep it to herself but will speak directly to you. Only then can your relationship remain strong and lasting.
9. If you could change one thing about me, what would it be?
This is a bold question, touching on sensitive areas. Even when your ego is on the line, you’re still willing to hear her thoughts about you. Many conflicts can be resolved after this conversation, with goodwill and openness. Small issues that have been bothering her for a while may not hurt much, but they’re still uncomfortable. Create a space where both of you are happy to address them together.
10. What does your ideal man look like?
Why should you ask this question? You don’t need to know exactly what her answer is, the goal is simply to see if she pictures you in her ideal man. If she likes you or pays attention to you, part of your personality or appearance will definitely show up in her description. I’ve tried this, and the answer was: “A man who truly understands and cares for me.”
11. What’s your biggest goal in life?
Everyone has dreams and goals, whether big or small. These desires are unique to each person. When you ask her this question, she’ll surely understand your genuine interest — that you want to know in order to support or at least encourage her. Pay close attention to what she says.
12. What’s your biggest fear?
No matter how strong a woman may appear, there are moments when she feels vulnerable. When answering this question, she might feel uneasy thinking about what scares her the most. Show her that you are a man of strength who can protect her from these fears.
