The 16 Best Flirty Questions to Ask a Guy

How are your flirting skills? 

Are you a master of drawing interest with nothing but your smooth talk? 

Well, if you’re here, chances are you need a little help. We get it! It’s hard to tell the line between a flirty comment and being weird or offensive. Plus, there are different degrees of flirting that are best for different situations. 

We’re here to help! 

If you are looking for some great flirty question to ask a guy, you can’t go wrong with these 16 options!

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Innocent Flirty Questions (Best for New Potential Partners)

Whether you’ve just run into your potential partner in a bar or matched through a high quality dating platform, there are social boundaries you aren’t prepared to cross. So, how can you be flirty with a guy you’ve only just met? Try out some of these questions!

“You Have Great [arms, legs, abs, shoulders, etc]. What Kind of Workouts Do You Do?”

This is a great flirty question because it allows you to sneak in a compliment that will make your guy feel good about himself and more comfortable in the conversation.

“If I was taking you on a date, where would you want to go?”

This is a great way to get someone thinking about the possibility of future dates and give you some good ammo to impress them later on. 

“Can You Show Me Your Best Pickup Line?”

A lot of men feel uncomfortable openly flirting for fear of being seen as a creep. This question gives them the opportunity to try some moves without fear of judgement. 

“If you could only eat one style of food for the rest of your life, which would you choose?” 

This is a conversation builder. It gives you an insight into his tastes, gives him a low-pressure opportunity to open up, and gives you important information for building future dates. 

Quirky Flirty Questions (Best for Making a Core Bond)

Flirting isn’t all about complimenting looks or trying to turn someone on. In fact, the goofier, quirky style of flirting is the thing that will help cement memories of you in his mind! So, if you are trying to enter a sillier, more personal place of flirting, try these lines:

If You Could Be Reincarnated As Any Animal, Which Would You Choose?

It’s not about actually believing in reincarnation, it’s about opening up the conversation in a way that is completely comfortable and free from consequences. This is a great question if your match/date is feeling shy or anxious. 

What Kid’s Movie Do You Still Watch As an Adult?

This is a great question for learning more about their childhood, level of sensitivity as an adult, and general interests. If you get some macho response like “ew, I don’t watch little kid movies,” you might want to be on the lookout for other unfun/ overly serious personality traits. 

If Money Were No Object, How Would You Spend Your Perfect Weekend?

You wouldn’t believe how much you can learn from this silly question. You can get a lot of insight into your date’s hopes and dreams. You can also learn a lot about their personality and how it matches yours. Some responses may even show you all the red flags you need to direct you out the door! 

What’s the Worst Date You’ve Ever Been On?

Gossiping isn’t always a good look, but sometimes you can bond a lot over commiseration. We’ve all been on terrible dates, so have a good time laughing about the weird situations you’ve been in and setting up call back/ inside jokes for later on. 

Flirty Questions With a Little bit of Spice (Best for Transitioning into a Sexual Relationship)

About half of the flirting we do leans more toward the sexual side of things. But you can’t just jump in with over the top questions that make your partner feel uncomfortable. First, you need to test the waters with some slightly saucy questions and flirts.

Which is More Romantic – Kissing in the Rain or Kissing Under the Stars?

It’s pretty obvious why this spicy question works: it gets him thinking about kissing you. We find that questions like these are perfect for transitioning a new relationship into something a bit more physical. 

Do You Know How to Give a Good Massage?

This is the type of flirty question that can transcend a relationship from verbal to physical. It also has the added benefit of coming with implied consent (though vocal, informed consent should always be acquired before touching your partner in a sexual manner). 

If I Tried to Kiss You Right Now, What Would You Do?

This one is a little more brazen, but should show you very quickly where you stand with your match/ date. It takes some guts to lay down a bold line like this, but it can help you move into the next phase of your relationship. 

When Did You Know You Were Into Me?

This is a common type of transitional flirt. It gets him to admit how into you he really is and you get to bask in a few compliments, which is always welcome! 

Truly Risque Flirty Questions (Best for Getting Your Partner in The Mood)

It’s time for the cheekiest, naughtiest, flirty questions. These are the ones you break out when you KNOW your partner is sexually interested in you. If you use these on your first date or during your first few conversations, you will likely scare him away! So, be certain the time is right so these questions are sexy and not creepy.

Do You Have any Kinks or Fantasies?

This is the kind of question you want to reserve for after the physical part of your relationship has begun. It is a great way to open up your mind to ideas and activities that can grow your intimate bond with your partner. 

Which Part of My Body is Your Favorite?

If you want to subtly let him know you have some sultry activities on the mind, drop this line. It is just innocent enough to not be awkward, but also easily leads to some less innocent activities. 

What’s Your Biggest Turn Off?

This is honestly an important question to ask him because you don’t want to accidentally do things that he despises. But, it can also help you learn if you are generally, sexually compatible. 

If We Were Alone In My House/Apartment Right Now, What Would You Want to Do?

You really want to clue him in to you being in the mood, this is the right question to ask. It makes it very clear what you are interested in and provides an open opportunity for some roleplaying, sexting, etc. 

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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.