Flirty Questions to Ask a Girl You Like: Interesting Ways to Learn More about Her

Regardless of what you heard, the truth is, flirting is an art. And, just like any art, it can be mastered and improved upon. If you are looking for flirty questions to ask a girl you like, you’re in the right place!

Of course, it helps to have natural charisma, but we’re not all blessed that way. So yes, there are ways to get better at flirting, techniques you can learn, and moves to master. But, the art of flirting is based on creativity and wits, and it only works best when two people are fully engaged.

My list of flirty questions to ask a girl you like is perfect to get you started in the game. Each of the questions on the list represents a cute, innocent way to get to know the girl you like. Even more, it will give you an opportunity to show how smart and funny you are, and it will open new topics for communication.

I divided the list of flirty questions to ask a girl you like into several categories, so make sure to choose the right one. If not, you run the risk of asking a question that’s too bold, too early in the relationship. This can easily ruin your game and put an end to what could’ve been a beautiful relationship.

Flirty Questions to Ask a Girl You Like Before the First Date

If you met online or you got her phone number but didn’t get the chance to ask her on a date, you have a bit of time to “put your charms on her”. You probably talk via text messages/chat so it’s important to show you are an interesting and funny guy.

You do this by keeping the conversation going, and there will be plenty of moments to sneak in some flirty question in the discussion. Here are some that usually work wonders:

What’s that like?” or “What was that like?

In itself, the question doesn’t look too flirty or even interesting, but let’s dissect it for a bit. First, it can be addressed in any situation, at any convenient time because it’s not too bold and it makes the girl feel desired and cared for. It’s also a way to keep the conversation going smoothly and it gives you a chance to get the girl talking about something she enjoys.

If you don’t think it’s such a big deal, you should know that great interviewers use it extremely often. While it may look simple and plain, this question shows you care, you pay attention to the girl you are engaged in conversation with, and you are interested in her.

Now, when to actually introduce this question in the conversation? For instance, if she mentions “I work for a big IT company”, your answer could be “Interesting; what’s that like?”. It’s enough to get her going about how she feels about her work and the conversation moves forward.

If she says “I spent my summer/last vacation in Miami” or “I grew up in North Carolina” or “I just finished reading this book”, in any of these situations, the “What was that like” question will connect with emotions and will get you closer to her heart.

“So, what’s cool about this place?”

One of the questions a guy asks when he first meets a girl at an event or a bar is “Do you come here often?”. While it is legit and it shows your interest in the girl, this question is boring and doesn’t give room for too much conversation.

Still, if you formulate it differently, you get to look interesting and interested at the same time. By asking what’s cool about the place, you learn if she comes there often and what she likes in a place (extremely useful information for an eventual first date).

“Are you single?”

This never shows up on the list of flirty questions to ask a girl you like and it is a direct and blunt question. But it is such a fantastic tool in your flirting arsenal! First, it shows you are interested, you are not afraid to be direct, and you don’t like wasting time. Second, it allows you to be more flirtatious once you get an affirmative answer.

Still, you shouldn’t open with this question. Start by saying hello and build up the conversation until you can ask it – this also gives you room to see if the girl is as interesting as you first thought.

“What’s your ideal date?”

This is the perfect question to ask before actually asking her on a date. You learn about her favorite ways to spend time with a date and you open the door for the big question.

Flirty Questions to Ask a Girl You Like On a Date

First dates can be awkward if you don’t come prepared. So prepare a series of topics that can be used as discussion boosters, but also think about cute questions to ask that will keep the conversation flowing. Here are some easy-to-remember ideas:

“So, what’s your story?”

This question comes as a replacement for the classic and a lot more boring “What do you do (for a living)?”. Basically, you’re asking the same question, but in a more unique and whimsical way.

If you want to get more out of her, ask what she’s passionate about. After all, we’re not all passionate about our job or current situation, so this question opens a whole new world of topics for you. It also allows her to share things she loves to do and puts a positive spin on the date.

“What’s the craziest thing you’ve ever done?”

It’s a conversation booster and lets you know if she loves adventure, flirts with danger, or just likes curling up with a good book from time to time. Of course, the question can bounce back so be prepared with an answer of your own.

Talking about crazy adventures can drum up adrenaline and arousal. (In psychology, arousal simply means being alert, awake, or attentive.) Thinking about your skydiving trip or bungee jumping adventure can get your heart pumping as it did when you experienced the event. Often, our minds misattribute this arousal for attraction. Being around someone that makes your heart race, whether it’s through their crazy stories or physical attractiveness, will make you want to see them more often!

“What’s your favorite holiday?”

The holidays we love tell a lot about ourselves! For instance, a person who loves Halloween and appreciates the idea of a good costume has a rebellious, artistic side and loves parties. On the other hand, someone who loves Christmas is more family-oriented and enjoys the beauty of a romantic evening by the fireplace.

It’s also a way to gather intel on how she likes to spend the holidays. If the relationship goes any further, you can use the information you get now to create the perfect couple holiday for her.

“If you could go anywhere in the world for two weeks, where would you go?”

Everyone likes to travel and we all have that dreamy location we want to cross off our bucket list. So this question is sure to produce a passionate answer that will entertain the conversation for a while. It’s also a way to let you know about her current state. For instance, if her first reply is “partying in Vegas”, then she might be bored with her everyday life.

On the other hand, if she wants to go to India or Tibet, she may be looking for spiritual enrichment. Also, a girl who wants to visit cultural places like Europe or Egypt may be interested in more such topics.

“There’s just something about you…I can’t put my finger on it. What do you think it is?” 

This is a fun question because it expresses your interest in her. Her response will also tell you what she likes about herself, or what people notice about her. Is it her charm? Good looks? Eye contact? The answer will give you a look into how she perceives herself.

Flirty Questions to Ask a Girl You Like After the First Dates

Now that you know a bit more about her, you can be bolder with your questions. But still, try to keep it light and casual; after all, you don’t want to scare her away. Of course, if she is into heavier topics, feel free to approach those as well.

“What’s your idea of an ideal man?”

After the first date you still want to keep things flirty and playful, but you don’t want to wait too long before taking things on a more serious note (that is, if you like the girl). This question reveals her expectations of a possible partner and lets you know if you actually have a real chance with the girl.

“What’s your best childhood memory?”

A great second-date question and a fantastic way to make her think about some of her favorite times of life! It’s also a great way to learn more about her past, her family, and the environment in which she grew up.

“Where do you like to be kissed the most?”

It is bold and it leads to a more intimate relationship between the two of you. It also shows you have no interest in a platonic relationship (if there was any doubt up to this point) and allows her to reveal something a bit more sexual.

Still, you must make sure it is the right time. For instance, you shouldn’t ask this question immediately after the first or second date. Maybe wait for a third date to go by and then ask it.

“Do you believe in love at first sight?”

This question doesn’t have to have a punchline – it can just be a legitimate question! Even if you aren’t in love, this gets the conversation going. When do you fall in love? How do two people fall in love? Is “love at first sight” just lust in disguise? These are all fun debates!

More Dating and Flirting Tips!

Asking questions is the best way to get to know your date! So, if you know you’re not a spontaneous person, get a list of questions and practice them before going on the date. Also, have answers prepared, in the situation the question returns to you.

Overall, the art of flirting is based on both partners being involved in the exchange, so if her answers are short and without substance, it doesn’t mean you’re bad at flirting. It might just mean she’s not that into you, and you should move on to someone else.

Curious to read more about dating and flirting? Check out the following pages:

Practical Psychology

Practical Psychology began as a collection of study material for psychology students in 2016, created by a student in the field. It has since evolved into an online blog and YouTube channel providing mental health advice, tools, and academic support to individuals from all backgrounds. With over 2 million YouTube subscribers, over 500 articles, and an annual reach of almost 12 million students, it has become one of the most popular sources of psychological information.

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