Tired of running out of things to say, hitting “dead points” in conversation, and losing a girl’s interest? These are common problems that a lot of guys face. But if you know good questions to ask a girl you like, you can avoid these problems, connect with women more deeply, and attract them with ease.

Here’s the main issue: When you have the same old conversations with women, you get stuck in “small talk mode”. You don’t talk about anything that really matters, and so, the girl never feels a connection to you. You keep digging and digging, but the conversation goes nowhere.

We’ve all been there. Soon enough, the awkwardness hits its limit, and the girl excuses herself to “find her friends” or go to the bathroom, never to return again.

It sucks, right? But if you knew some great questions to ask a girl, you’d be in a much better position.

So today, I’ll give you questions to ask a girl in just about any situation you’ll face. From the first time you meet her, all the way up to when you’re considering a relationship with her. You’ll be covered.

These questions will help you not only flirt and connect with her, but also get a sense of her values as well as whether or not she’d make a potential good girlfriend for you.

Of course, you shouldn’t take her question by question like an interview. These are just questions to put in your back pocket and help you build the conversation. Keep that in mind as we go along.

Sound good? Let’s get into it.

Bonus: Get free access to my new course and learn the 5 conversation mistakes that put you in the friendzone.

Here are 23 Good Questions to Ask a Girl You Like…

Good Questions to Ask a Girl When You Meet Her for the First Time

1. What are you up to?

This tells you her logistics. You’ll know whether she’s in a rush or has some time to talk, and you can structure the conversation from there.

If she’s in a rush, you can go for her number quickly and excuse yourself from the conversation. But if she has some time to talk, you can connect and flirt with her a bit to make the interaction more solid, and improve your chances of seeing her again.

2. What brings you to this city?

Her answer will give you a quick snapshot of her background. You’ll know whether she’s living there, a tourist, or from there. It might even give you some insight into her career and passions.

Good Questions to Ask a Girl When You Want to Connect With Her on a Deeper Level

3. What are you passionate about?

A a woman’s passions can tell you a lot about her. They also give you a glimpse into whether you are a good fit for each other. You may find that you have similar passions, which makes it very easy to relate and connect with her.

4. What’s something you’ve always wanted to do? 

This gives you insight into her dreams and aspirations. Perhaps she’d love to paint, travel the world, or start a business.

Given the opportunity, most people would love to talk about their dreams and aspirations, but they hardly ever get asked about them. And so, it brings up all sorts of good and hopeful emotions.

5. What do you do for fun in this city?

This is a great question, especially if you’re a single guy in a new city. You’ll learn a bit about what the locals like to do for fun, and you’ll learn about the kind of activities the girl enjoys. This can give you some good ammo when it comes to trying to figure out potential dates.

6. What made you want to get into that? (i.e. her career, a specific passion, etc.)

Most men never dig deep enough to discover why a girl actually wants the things she wants. And so, this acts as a bit of a pattern interrupt – it goes beyond polite conversation and small talk.

7. What’s your dream job?

This question gives you a better idea of who she is and what her future plans are. Is she ambitious? Driven?
It can also lead to a meaningful discussion for her – and you build trust with her as she confides with you.

8. If you could wake up anywhere in the world tomorrow, where would it be?

Most people like the idea of traveling somewhere interesting in the world. This question gets her in the adventurous spirit, which is good for you. She’ll be more open to having adventures with you on the date, and afterward.

Good Questions to Ask a Girl When You Want to Create a Flirty and Fun Vibe

9. What do you find sexiest in a guy?

You can transform the vibe from platonic to sexual with this question. It works well because it gets her to look at you through a more sexual lens. Maybe she hadn’t really thought about in a sexual way yet – but this question can certainly make things interesting.

10. What’s one thing I wouldn’t guess about you?

This is one of my favorites. It gets her to open up a little more and tell you something she probably doesn’t tell a lot of people, and in return you can tell her something surprising and interesting about you.

As a result, you both become a little more invested in the date and in each other. Plus, it makes for a fun conversation topic.

11. What kind of music do you love to dance to?

Dancing is a fun topic. Most women enjoy dancing and feel good when they do it. So when you ask them about it, and can bring those good feelings to the surface.

Plus, it gives you a good reason to bring her back to your place later in the date or interaction. For example, you can say, “Let’s head back to my place and listen to some of that reggaeton music you were telling me about…”

12. Do you have rhythm?

This is a good question to ask when you’re on the topic of dancing. It’s an easy transition.

Rhythm is a tell-tale sign as to whether or not a girl as good at sex. If a girl has terrible rhythm on the dancefloor, she probably won’t be very good in bed. And so, this question gives some insight into her sexual side.

It also gives you an opportunity to create sexual innuendo. If she says she has good rhythm, you can joke, “That’s great… rhythm is important for a lot of things,” with a sly smirk on your face (insinuating that rhythm is also important for sex). This is one of my go-to’s and it’s great for drawing a laugh and making the vibe more sexual.

13. What kinds of things make you laugh the hardest?

This question gets her in a fun mood – after all she’s thinking about things she finds hilarious. It’s a great question, especially when the interaction seems a little too serious and you want to lighten the mood.

Good Questions to Ask a Girl When You Want to Qualify Her

14. Do you like to cook?

It’s awesome to hang out with a woman who can cook well. You can count on her to cook some incredible meals for you and it adds more depth to the dating experience. What’s more, it adds to her long-term potential

15. Do you enjoy working out/going to the gym?

It’s great if a girl looks sexy and fit now – but what is she going to look like in a few years? This question gives you the answer.

If she doesn’t like to go to the gym or exercise, then don’t count on her maintaining that fit look for long. I don’t know about you, but I like girls who are sexy and in shape. Not only does it show that she values her health (which is important to me), but it also makes sex more fun. So when a girl says something like, “Ugh, I hate working out!” or, “I used to, but I got bored,” that’s a huge red flag.

16. What are you favorite kinds of foods to eat?

This tells you about whether or not she likes to eat healthy. If her favorite foods are pizza, burgers, and fries, that’s probably not a good sign.

17. Do you consider yourself to be a creative/adventurous person?

It doesn’t have to be creative or adventurous – you can use pretty much any trait that is important to you. The point is to get her to qualify herself as to whether or not she embodies that trait

Good Questions to Ask a Girl Before You Consider a Relationship

18. Have you ever cheated in a past relationship?

If she’s cheated in the past, odds are she’ll probably cheat again in the future. You can also get some insight into the way she talks about cheating.

Maybe she says, “I never hooked up with another guy when I had a boyfriend, but I did talk to guys on Tinder,” or “I did flirt with this one guy from work all the time.”

If she has a nonchalant attitude about it you can tell that she’s rationalizing it, it’s a sign that she might not be the best relationship material.

19. Do you have a good relationship with your parents?

Your relationship with your parents goes a long way into shaping who you are as a person. And the same goes for women.

Her relationship with her parents will affect the way she acts in her romantic relationships, and it also affects her own parenting strategy if and when she eventually has kids. Usually, the better relationship she has, the better her coping strategies, and the more stable she’ll be within her romantic relationships.

20. What’s been your best romantic relationship, and why did it end? 

You’ll learn what worked and what didn’t in the romantic relationship that she remembers the most fondly. This can give you clues as to how to treat her within your relationship if you want to make it last long.

21. Have you ever had an STD?

This tells you a bit about her sexual history and sexual health. It’s just generally a good thing to know before you get in a relationship.

22. If you had $1 million, what would you do?

This question tells you a lot about the way she makes financial decisions and views money in general. Consider what you’d do with a million dollars, and compare it with her answer. The more similarly the two of you view money, the better chance the relationship has of working out in the long run.

23. If you could give advice to your 5-years-ago self, what would you say?

Her answer will tell you about her ability to learn from her mistakes, as well as the way she views the choices she’s made in her life. You’ll learn if she has a mentality of self-improvement, or if she kind of goes with the flow and lets life happen without trying to direct it.

Wrapping Up Good Questions to Ask a Girl You Like…

You now have a set of questions for any stage of a relationship with a girl you like. From the moment you say hello, all the way to the point where you’re considering a relationship with her.

Keep these in your back pocket and use them to fuel your conversations.

What are some of your other favorite questions to ask a girl you like? Let me know in the comments below.

And be sure to check out the video version of this post below!