Deep, Flirty, and Dirty Questions To Ask Your Crush

We all know that guy or gal that starts every conversation with “Wyd?” and never strays beyond that surface-level small talk. You ask them about their most embarrassing memory, and they reply with “IDK, u?”.

It’s all too common. Not to mention unbelievably annoying. A dry conversation doesn’t get you anywhere, especially if you’re trying to win over your crush.

Talking is how we make meaningful connections, create inside jokes, and, most importantly: make our intentions clear. Dirty questions are a fantastic way of doing that. They open the door for flirty conversations and allow you to indirectly exclaim your feelings. They're also just so much more interesting than a typical ‘get-to-know-you’ chat.

Whether you’d rather ask juicy questions about their sex life, play a round of dirty truth or dare, or find out the craziest thing they’ve ever done on a night out, you’ve come to the right place!

Here's what we'll cover:

You never know the roads these questions could take you down!

Freaky Questions

Asking your crush freaky questions is a great way to move the conversation into more flirty territory. The key to asking the best freaky questions is to read the room but be suggestive without being overly vulgar (unless you know they're into that, of course).

You want to gauge what boundaries you can push without making your crush uncomfortable. If you already have a good, flirty vibe going on, then you should have the green light for some spicy questions!

Go for something like:

  • What’s the weirdest thing someone has said to you during sex?
  • Have you ever been skinny dipping?
  • Have you ever messed around in a public place?
  • Do you have a bucket list of places you want to have sex in?
  • What’s the dirtiest dream you’ve ever had?
  • Do you like to use toys?
  • What’s your guilty pleasure?
  • Eye contact or no eye contact during sex?
  • Do you like to make the first move?
  • Where do you think my favorite place on my body to be kissed is?
  • Would you ever wear edible underwear for a dare?
  • Do you think I’ve ever had a one-night stand?
  • What would you think the dirtiest thing I’ve ever done is?
  • How would you describe your best and worst orgasm?
  • Do you have any weird kinks?
  • When was the last time you masturbated?

The exciting thing about these questions is that they open the door to allusive conversation. By asking your crush about dirty topics in a fun and unconventional way, you’re associating yourself with excitement, secrets, and sex in their mind.

It's even more so when you ask them to guess dirty things about you (now they’re thinking about you in all kinds of compromising situations - wink wink).


Truth Or Dare Questions

The game we all know and love: Truth or Dare.

The beauty of this game is that if you play with your crush, and they pick truth, all expectations of a reasonable and modest question are off the table. By just playing truth or dare, it’s essentially an unspoken rule that all of the most personal, nasty, and naughty questions are on the table. No backing out!

So how should you use your newfound truth serum? By asking the dirtiest things you can possibly think of, of course!

  • Have you ever been caught having sex?
  • Do you have a sex tape?
  • Have you ever had sex while someone was sitting in the next room?
  • What’s your favorite position?
  • Have you ever played strip poker? (This also makes a good dare!)
  • What is the most amount of people you’ve slept with in 24 hours?
  • Who would you choose if you could pick any two people to have a threesome with?
  • What is the weirdest sex toy you’ve used?
  • Where’s the weirdest place you’ve put it?
  • How many partners have you had?
  • Have you ever been in an open relationship? Why or why not?
  • What’s the most shameful porn you’ve ever watched?

Truth or Dare is probably one of the best ways to get to know someone. I mean, you can get juicy information out of them and use imaginary game rules to insist that they play along!

Jokes aside, while it’s an incredibly fun game, you should never forget to respect people’s boundaries. If you sense their discomfort with the questions, just tone down the intensity! Games are meant to be fun for everyone; after all, make sure you’re on the same page about what kinds of questions you’ll be asking each other before you start!


Cute Questions

You can be suggestive and still be coy. It’s an art form, I assure you.

Maybe you like to leave something to the imagination but still want to show your crush you’re interested, as well as create the sense that there is more to what you’re saying than meets the eye.

If that sounds like you, do continue!

  • Are you a little spoon or a big spoon?
  • What was your first kiss like?
  • What’s your favorite thing to do on a first date?
  • What attracts you to a person?
  • Have you ever online-dated?
  • What is your favorite body part of a man/woman?
  • If we were on a first date right now, what would we do?
  • What’s your love language?
  • Do you ever see us having a romantic relationship?
  • What has been your worst date, and why?

These cute questions are definitely not so much on the dirty side, but they allude to the idea of sex and romance without having to be quite so overt about it.

It’s the perfect strategy for someone a little more reserved or perhaps if you’re still in the ‘getting-to-know-you stage’ with your crush and don’t want to ask them outright what their favorite sex position is!


Flirty Questions

Being direct when talking to your crush can be a little daunting. But it’s also a really effective way of sparking some flirty conversation and possibly opening the door to a new relationship. It can be tough to figure out what to say when you want to be direct and to the point with your crush.

Here are some flirty questions to ask that should really get the conversation ball rolling and make your intentions clear as day!

  • How do you feel about me?
  • Do you enjoy being single?
  • What is your favorite thing about me?
  • Next time we hang out, what do you want to do?
  • What’s one thing you’ve always wanted to say to me?
  • Do you ever think about me?
  • If I said I liked you, how would you respond?
  • What reminds you of me?
  • Do you ever think about getting into a new relationship?
  • How do you think I feel about you?
  • Do you want to add me on (insert social media app)?
  • What do you think our first kiss would be like?
  • Do you want to know what my favorite part of your body is?
  • What’s something you’ve always wanted us to do together?
  • Would you like it if I took you to my favorite spot?
  • If we were on a date, who do you think would make the first move?
  • Do you see us together?
  • What was your first impression of me?

You see, ‘flirty’ doesn’t always have to mean beating around the bush with a wink and a nudge. Some people appreciate a more forward kind of flirting, where you take the conversation very clearly in the suggestive direction you want to go in.

The beauty of these questions is that the intention of why you’re asking them is obvious, but they’re just the right amount of conversational so that it wouldn’t be too awkward for your crush to steer away from the topics if they’re not interested.

Really, this is one of the best selections of questions to use if you hate living in the unknown and would rather jump straight into the deep end to see where you stand (with a metaphorical ladder nearby, of course, in case they indirectly turn you down).

If worst comes to worst, and they don’t answer the way you want them to, these questions still make for some genuinely interesting conversation starters!


Funny And Embarrassing Questions

Funny questions are a great way of getting the ball rolling on some potentially dirty conversation and maybe even dirty secrets. The brilliant thing about funny questions is that they keep conversation light and airy when discussing sex and relationships.

Flirting can be pretty heavy-handed, but by slotting in some awkward questions and digging around their mind for a little comic relief: you’re associating yourself with humor and fun.

Laughing together is a great bonding experience, and jokingly laughing at your crush is also a good way to establish a slight playful dominance if you’re so inclined. That part is a bit of a niche goal, but I know some of you freaks are out there!

So let’s get into those funny questionable questions!

  • What’s your favorite condom color?
  • What’s the most embarrassing thing that’s ever happened to you during sex?
  • Would you ever go to a nude beach? Why or why not?
  • What’s the weirdest thing someone has ever asked you to do to them? Did you do it?
  • What’s the worst thing you’ve said to someone in the middle of sex? What did you say?
  • Has anyone ever walked in on you during sex? What happened?
  • What’s the dirtiest thing you’ve ever done by yourself?
  • Who’s your weird celebrity crush?
  • What’s your worst dirty talk story? (Everyone has one, and they’re all cringe)
  • Have you ever masturbated in a weird place?
  • What’s the craziest thing you’ve done with another person?
  • Has anyone ever accidentally seen your search history? What was on there?
  • Have you ever used a sex toy wrong?

Deep Questions

One of the best things about sex is that everyone talks about it in a different way and has a different experience with it. For some people, it’s a beautiful, intimate, and sensual experience that deserves some really in-depth conversation.

Everyone loves deep late-night chats, but they’re even better when you’re diving into the topic of sex on a personal and meaningful level. Borderline dirty talk with your crush is an experience in and of itself, but getting hot and heavy on an insightful level is just a whole other thing.

Just give it a try; you’ll see what I mean. Everyone gets off on feeling like they’re in a deep, coming-of-age movie. Don’t pretend you’re above it; you can’t fool me!

  • What does sex mean to you?
  • Do you think sex is the most essential part of a relationship?
  • Did you learn anything from your last sexual encounter?
  • What kinds of intimacy are important to you?
  • Do you think sex has changed your identity in any way?
  • What does your ‘perfect’ sex life look like?
  • Are you at peace with your sexual identity?
  • What makes you feel attractive?
  • Do you separate sex and emotion?
  • What’s your opinion on porn?
  • What are your sexual and emotional weaknesses? Strengths?
  • Have you ever regretted being with someone? Why?
  • How do you feel about casual sex?
  • What was your very first orgasm like?

The reason I think these deep questions are important is that they open up a dialogue and would hopefully allow you and your crush to be vulnerable with one another. You want to make sure you know each other well enough before you start diving into their brain for an emotionally and sexually charged chat, but when you do, I can almost guarantee it’ll be worth it.

Sharing personal thoughts and insights with another person creates an intense connection, and it’s a whole lot more interesting than the dreaded ‘So, um, you a virgin? Lol’ texts. Ugh.


Final Tips

All in all, dirty questions don’t have to be so simple and boring. There are layers to discover when you want to initiate a spicy conversation or a Truth or Dare game with your crush.

One size absolutely does not fit all, and you have to take into account what kinds of questions your crush would enjoy answering and what types of questions you yourself would feel comfortable asking!

Coming up with organic topics to get your crush interested in you and get their mind on ‘sex! sex! sex!’ is a challenge in itself, and that’s exactly why incorporating these questions into a late-night texting game or on a drunken date is so effective!

It’s fun, it’s funny, it’s sexy, and overall it’s just a great way to get to know each other. Stories and new topics can branch so breezily from these questions that it might be 6 am before you know it, and somehow you’ve been waist-deep in random questions and flowing conversation for six hours!

That is the beauty of carefully calculated and well-thought-out questions. You never know the roads they could take you down!

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