25 Flirty Questions to Ask a Girl

When it comes to talking to ladies, there aren’t any flirty questions that are one size fits all. You need to consider the personality of the girl you’re interested in, their hobbies, and the things they might find flattering. 

To help you find the right questions, we’ve broken them down into 5 personality categories – fashionistas, sporty ladies, creative types, alt girls, and intellectuals. 

Disclaimer: this is not an exhaustive list of personality types. In fact, some women can even fit into multiple personality types. This list is just a starter guide to help you find some flirty questions that may work for you! 

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5 Flirty Questions For Fashionistas

1. “If you could remove an item from my outfit, which would it be?”

This one is a bit cheeky! Not only can she give you some gentle ribbing, but the insinuation of removing your clothes makes this question extra flirty. 

2. “Those shoes look uncomfortable! Do you need a foot rub?”

This one is a bit forward, so make sure you ask in a way that is clearly joking. If you play it right, that foot rub might actually happen! 

3. “What is the sexiest thing a man/woman can wear?”

If she picks up the bait on this one you might get an answer that reflects something you are wearing. Either way, this can spark a conversation that can guide your style moving forward. 

4. “Do you want to come over and roast award show outfits with me?”

Rating red carpet outfits is basically like Netflix and chill for people who love fashion. Not only is it a cute date idea, but you’ll likely end up making a deep connection throughout the evening.

5. “Is there something a date could wear that would instantly turn you off?”

Not only will you learn some valuable information about her attractions, but the subtle reference to sexual intimacy makes this question one of the flirtiest you could ask. 

5 Flirty Questions For Sporty Ladies

1.  “What athletic feat are you most proud of?”

This is a great question to get her talking about herself. It will make her feel good to brag a little, and you will get lots of great information to use in future conversations. 

2. “Which teams are your favorite and why?”

Mild, playful teasing is a great flirting technique. This question is a great way to open the door to laughing over rivalries and other sports fan quirks.  

3. “Could you teach me to play X?”

If you want your flirting to lead to more dates, you should be sure to open up her mind to ideas of things you could do together that she would enjoy. 

4. “Is there a sport or activity you’ve always wanted to try?”

This is a similar approach to the last question, but without putting the pressure on her to curate the date activity. This question gives you the opportunity to create a dream date for her. 

5. “Would you be open to a little friendly competition?”

This is the type of flirt that can lead to physical, lighthearted affection. It is a great transitional flirt and shouldn’t be used the first time you meet her (it might be seen as creepy or goading). 

5 Flirty Questions For Creative Types

1. “Do you prefer spending time at home, in nature, or at a party?”

Creative types aren’t always introverts. This question lets her know that you recognize that she has a unique personality that doesn’t fit into a mold. 

2. “Would you show me some of your art?”

Always come up with a way to let her brag about herself a little. It will boost her confidence and help you learn more about her. 

3. “Do you believe in muses?”

You could follow this up with, “maybe I could be your muse.” It is silly and lighthearted, but hints at your desire to be in a steady relationship. 

4. “Could you teach me to paint/draw/sculpt/etc.?”

This shows her that you are interested in her hobby. It may even lead to another date! 

5. “If I wrote you a song/poem/story, would you find it romantic or cheesy?”

This is a great question because it can lead to some funny conversations, help you lead into a comedic area of flirting, or open up the communication to a place where you can be vulnerable. There are so many ways it could go, and they are all positive! 

5 Flirty Questions For Alternative Girls

1. “Who do you think is the most underrated musical artist?”

If you want a flirty question that will open up a lengthy and interesting conversation, this is the right one! Be open to the idea of listening to her pick, and avoid negging her musical choices (or any choices for that matter).

2. “If I was open to anything, how would you dress me?”

You might end up with some cool style tips if you ask this question. More importantly, you are letting her know how much your respect her style. 

3. “Would you be interested in going foraging with me?”

This is not only a fun date idea, but the cottage core aesthetic is very popular in alt culture. She will likely be impressed with the thoughtfulness of this request.

4. “What is the most peculiar thing you own?”

Alt girls almost always have a collection of some unique items. This question opens up the door to discussing some of her favorite things so you can learn more about her hobbies. 

5. “Is there any body mod that turns you off?”

Alt women are usually into body modifications, but even they have their limits. We love flirty questions that allude to attraction and passion, as they can lead to a closer connection between you and your date. 

5 Flirty Questions For Intellectual Women

1. “What is a fun fact you love to talk about?”

Intellectual women love to be able to nerd out without being talked down to. Create that safe space for her! 

2. “If you could make a career out of any field of study, which would you choose?”

This question will show you how ambitious and impressive she really is. Use the information you learn to fuel future date/gift ideas.

3. “What’s the best book you’ve ever read?”

We love this question because she will love this question. Plus, you’ll get a great reading suggestion out of it! 

4. “What do you like to do when you want to turn your brain off?”

Having to think all the time is exhausting! Help her show you the best way to get her  comfortable on your dates by learning what she likes to do to relax. 

5. “What is something you’ve always wanted to see or do?”

This is another flirty question that gives you important details about your date/love interest. Keep her answer tucked away in your memory files and use it to surprise her with an amazing date in the future! 

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.