Remember These 20 Questions to Ask a Girl to Keep a Conversation Going

A real conversation always contains an invitation. You are inviting another person to reveal herself or himself to you, to tell you who they are or what they want.

– David Whyte

You’ve finally plucked up the courage to go talk to that girl you’ve been eyeing up from across the bar, and now you’re stuck. You want to keep the conversation going, but you’re not sure what to say.

You don’t want to say something generic like “so what do you do?” or “where are you from?”, but you also don’t want to say something so random that it freaks her out. What can you do?

I asked our on-staff pickup artist, Mike Perez, for his advice. “You want to keep the conversation light and playful. Ask her questions that make her think, but don’t be too serious. And most importantly, make sure you’re having fun yourself. If you’re not enjoying yourself, she’ll be able to see it and it’ll put her off,” says Mike.

Below is a list of questions that you can use that are balanced just right between being playful, flirtatious and open ended enough to further extend the conversation:

1. When you are alone, what’s your favorite thing to do?

This is a great question to ask because it not only shows that you are interested in getting to know her as a person but it also has the potential to lead to some very interesting responses. It’s also a question that can lead to a lot of different directions.

She might tell you that she likes to read, or she might tell you that she likes to go out and party. She might say something surprising like I love to tie men up and ride them all night long. You won’t know until you ask!

Either way, you’ll be able to get a better sense of who she is and what she likes to do.

2. When’s the last time you got butterflies and why?

“Butterflies” is a great topic to bring up because it’s something that we can all relate to. We’ve all had that feeling of nervous excitement before, whether it’s before a first date or a big presentation at work.

By asking her about the last time she got butterflies, you’re opening up the conversation to talking about some of her more thrilling and exciting experiences, which can be a turn on. She’ll likely start talking about something that made her happy, which is a great foundation for further conversation.

According to Mike, “Anything you can ask that might excite her is good. Keep going in that direction.”

3. What’s your stance on manscaping?

Manscaping is always a fun topic, especially when you’re talking to a girl. It’s a great way to gauge her sense of humor and whether or not she’s down to experiment.

Some girls are totally into it and think it’s hot, while others find it weird and off-putting. Either way, it’s a great conversation starter and can give you an insight into her sexual preferences.

“If she’s down to talk about manscaping, it’s a good sign that she’s open to talking about sex. You can take the conversation in a lot of different directions from there,” says Mike.

4. Who’s your biggest celebrity crush?

We all have that one celebrity that we can’t help but swoon over, no matter how unrealistic it may be. This question is a great way to find out who she’s attracted to and what kind of guys she goes for.

It’s also a fun question to answering because we all like to talk about our crushes. And who knows, maybe you have something in common with her celebrity crush. If she says she likes tall, dark and handsome men and you fit that description, you might be in luck.

5. So what’s your guilty pleasure?

We all have those things that we love that we’re maybe a little bit embarrassed to admit. It could be a show like The Bachelor, a passion for fashion or a love of all things pink.

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By asking her about her guilty pleasure, you’re opening up the conversation to talking about some of her more fun and interesting likes and dislikes. This is a great question to ask early on in the conversation because it can help you find some common ground.

If she likes The Bachelor and you’ve never seen it, you can use that as an opportunity to ask her why she likes it. From there, you can then start talking about your own TV guilty pleasures.

6. What’s the most daring thing you’ve ever done?

This is another question that can lead to some interesting stories. If she’s done something adventurous like skydiving or bungee jumping, she’ll likely have a funny or exciting story to tell about it.

Even if she hasn’t done anything that daring, she might still have a story about a time when she took a risk and it paid off. These types of stories are usually laced with strong emotions, which make for good conversation.

7. Do you like your life or would you like it to be different?

This question is a great way to get to know someone on a deeper level. It’s also a question that can lead to a lot of follow up questions.

If she’s happy with her life, you can ask her what she likes about it. This will help you get to know her values and what’s important to her.

If she’s not happy with her life, you can ask her what she would change. This can lead to a conversation about her goals and what she’s working towards.

Both of these directions can be interesting and informative conversations that can help you get to know her better.

8. Have you ever gone skinny dipping?

This is a flirty question that can lead to some fun banter back and forth. Skinny dipping is definitely a daring thing to do, and it’s something that not a lot of people have done.

If she says yes, ask her where she went and if she liked it. If she says no, ask her if she’s ever wanted to try it. Again, you’re trying to keep the conversation light and fun while also being open ended so that you can keep talking.

9. What attracts you to a guy?

This is a great question to ask because it gets her thinking about the qualities she looks for in a partner. She might start talking about physical attributes, but she might also mention personality traits or even lifestyle choices.

Use this question as an opportunity to learn more about her and see if you have anything in common. If you share some of the same qualities that she’s looking for, she’ll be more likely to be attracted to you.

10. What’s the baddest thing you’ve ever done?

This is a great question to ask because it’s unexpected and it’s a great way to find out if she’s down for some fun.

“You want to see if she has a bad streak in her. We all have a little bit of bad in us, and it’s an attractive quality. It shows that she’s not afraid to let loose and have a good time,” says Mike.

It’s also a question that can lead to some interesting stories, which is always a bonus. If she starts telling you about the time she got arrested for streaking through the park, you know you’re in for a good time.

11. What’s the craziest thing you’ve ever done?

This is another great question that can lead to some exciting stories.

“If she’s done something crazy, it shows that she’s not afraid to take risks. And that’s always a turn on. It shows that she’s spontaneous and down for anything,” says Mike.

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This question is also a great way to gauge her sense of humor. If she can laugh at herself and the crazy things she’s done, you know you’re dealing with a fun and easy-going person.

12. Where would you like you like to travel to most?

This is a question that’s both personal and open ended. It allows her to share her dreams and aspirations with you, while also giving you more insight into who she is as a person.

If she mentions a place that you’ve been to before, you can then talk about your experiences there and bond over shared memories. If she mentions a place, you haven’t been to, then you can ask her about what she’s looking forward to doing there.

“You want to find commonalities between you and her so that you can create a connection,” says Mike. “The more of a connection you have, the more likely she is to be interested in you.”

13. It’s your last day on Earth, what would you do?

This is a fun question to ask because it’s not something we think about very often. It’s also a great opportunity to find out what she’s passionate about.

If she says she would spend time with her family, then you know she’s close to them and values those relationships. If she says she would travel to a certain place, then you know she’s adventurous and likes to explore.

No matter what she says, you can use it as a starting point for further conversation.

14. What’s your idea of a perfect date?

This question is a great way to find out what kind of person she is and what she’s looking for. Does she prefer a night at home with a good book or a night out on the town?

If she’s the type that prefers a night at home, you can follow up with questions about her favorite book, movie, or TV show. If she’s the type that prefers a night out, you can ask her where her favorite place to go is or what her ideal date would be.

No matter what her answer is, you can use it as a jumping off point for further conversation. And if you find out that you have similar interests, you can use that as an opportunity to suggest doing something together that you both would enjoy.

15. If you could live anywhere, where would it be?

This question is not only a great conversation starter, but it’s also a great way to learn more about her.

Where she chooses to live can say a lot about what she values. For example, if she chooses to live in the city, it might mean that she enjoys the fast pace of life and being surrounded by people. If she chooses to live in the countryside, it might mean that she enjoys peace and quiet and being close to nature.

It’s also a great question to ask if you’re considering asking her on a second date. If she says she loves the city but you live in the suburbs, you can suggest meeting in the city for a date. Or if she says she loves the countryside but you live in the city, you can suggest taking a day trip out of the city to somewhere nearby.

Asking her about her dream life can give you a better understanding of who she is and what she wants out of life. It’s a question that can lead to more serious discussion, but it’s also a question that can be taken lightly if the conversation starts to die down.

By asking her about her dreams, you’re also giving her a chance to open up about her hopes and aspirations, which can be a very intimate thing.

16. What’s your favorite thing about yourself?

This question is open-ended enough that it can lead to a lot of different topics of conversation. It’s also something that most people don’t get asked often enough, so she’ll likely be caught off guard at first.

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That being said, it’s important to listen to her answer and then follow up with more questions about that topic. If her favorite thing about herself is that she’s a great listener, ask her about a time when she really connected with someone and what that felt like. If her favorite thing about herself is her sense of humor, ask her to tell you a funny story.

The goal here is to get her talking about herself in a way that is fun and engaging, so that she’s more likely to be interested in you.

17. Who are you closest to in your life?

This question is a little bit more personal than the previous two, so you’ll want to make sure that the conversation is going well before you ask it.

When she answers, follow up by asking her why she’s closest to that person. What is it about that person that she loves? What have they been through together? This question can really help you get to know her on a deeper level and find out what matters to her.

By asking her about the people who are important to her, you’re showing her that you’re interested in learning about what’s important to her. This is a great way to build a connection and create rapport.

18. What would you do if you won the lottery?

This question is a great way to get her to start thinking about all the possibilities that life has to offer. It’s also a fun way to get her to start thinking about what she would do with a large sum of money.

If she starts talking about all the things she would do with the money, you can start asking her about her dreams and what she wants to achieve in life. This can be a great way to get to know her on a deeper level and find out what’s important to her.

If she says she would give it away to charity, you can ask her about the causes she is passionate about and why she feels strongly about them.

19. If you could have any superpower, what would it be?

This question is great because it’s both fun and open-ended. It’s the perfect opportunity to find out more about her personality.

If she says she would want to be able to fly, you could ask her where the first place she would fly to would be. This question can lead to a fun conversation about travel and bucket lists.

On the other hand, if she says she would want to be able to read people’s minds, you could ask her if she would use her power for good or for evil. This question can lead to a more playful and flirtatious conversation.

20. Are you a Marvel or DC comics kind of girl?

Marvel vs DC comics is a great question if you’re talking to a girl who likes nerdier things. It’s a playful way to ask about her interests and it can lead to a longer conversation about comic books, movies, TV shows and other nerdy topics.

Even if she’s not into comic books, you can still ask her this question and follow up with asking about what kind of movies or TV shows she likes. “You want to find commonalities so that you can bond over shared interests,” says Mike.

If you can find something that the two of you have in common, it’ll be much easier to keep the conversation going. And if you’re both able to geek out about your favorite comic book character or TV show, even better!

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