Flirty Questions To Ask Your Crush To Win Them Over

There are so many ways to structure a first date with your crush in order to win them over. First of all, you have to be confident and strike the right balance between cocky and smooth. You want them to be impressed with you, right? Here’s a selection of ideas for flirty questions to ask your crush to win them over.

  1. Do you come here often? This is a classic standard response. It draws on all the classic rom-com standards of quips, without being creepy or overplayed. It shows that you can have fun and you aren’t taking things too seriously. That takes the pressure off for the other person. It means they can relax into the date. That means they’re more likely to ease into the date and show you their true self. That’s when the true flirting can commence, so it’s an essential stage.
  2. What would you do if I kissed you right now? Admittedly, this will take a little bit of courage on your part since it is pretty forward, but this is one of the best flirty questions to ask your crush. This is especially true if you actually have the nerve to follow up on it by actually kissing them!
  3. Do you like cuddling? Most of us appreciate the joys of cuddling with the person we like, especially during those early, butterfly-inducing stages of the relationship. Asking your crush if they also like to cuddle tells you how they feel about affection and also puts the idea in their mind that you might like to do it with them.
  4. Do you want to be the big spoon or the little spoon? This is a good follow-up to the last question, especially if they say they’re into it. If they do like to cuddle, ask them whether they want you to spoon them or vice versa. They won’t be able to stop thinking about getting up close and personal with you. After all, spooning is one of the most intimate ways to be physically near someone.
  5. What do you wear to sleep in? What if they sleep naked? If they’re not shy, they might admit this. Of course, it’s possible that the answer will be a little less than glamorous and they actually have an old ratty t-shirt and stained pair of sweatpants that act as their pajamas. Either way, this is still a great flirty question to ask.
  6. What’s your family like? This might not seem like a particularly sexy question to ask, but you’d be surprised. Once you have a strong foundation of understanding what drives them and their goals, you will find it much easier to tailor your flirting approach. For example, if they turn out to be a more serious person, then maybe teasing them endlessly isn’t the vibe. Meanwhile, if you’re chatting with a younger, happy-go-lucky person, that’s the time to start bantering. It’s all about reading the room and that takes research.
  7. Who are your closest friends? By this point, you know the person across from you pretty well, so it’s a great time to start amping up the intimacy of the conversation. Ask them about their friends and relationships. That builds intimacy and ensures that you can tap into deeper conversations. That’s the secret to flirting, after all. It’s not about endless quips and constructed conversations. It’s honesty and vulnerability. That’s where you get the most powerful relationships, from the trust you build.
  8. Am I your type? Once you’re comfortable with each other, go more direct. Ask them questions, like if you’re their type. It will give them a chance to either lie and save face, to end things, or to reveal that they are interested in you. It narrows down the options and clarifies the ambiguity inherent to the talking stage. This means you can accelerate your relationship with your crush – on your terms.
  9. What’s your biggest turn-on? What is it about a person that really gets them going? Is it a specific physical feature? A personality trait? Maybe they really like people who are intelligent and well-read. Maybe a sense of humor seriously turns them on. Or, maybe they’re a simpler person and there’s nothing sexier than a shapely backside or big boobs. Either way, this could steer the conversation in a really interesting direction.
  10. What’s your favorite body part on me? What about on yourself? This is another one of those amazing flirty questions to ask your crush. Of course, you’ll need to be prepared for what they have to say in response, and also be open to things getting pretty intensely sexual, especially if they’re quite open with the truth of their answer.
  11. Do you believe in love at first sight? If you’re someone who does, it’s good to know you’re preaching to the choir. If your crush doesn’t, things might get a little heated here, but in a good way. Challenge one another, express your viewpoints, and make them see why love at first sight is not only real, but it might exist between the two of you.
  12. What should we do the next time we go out? This is, again, direct, but it shows that you have an expectation to have another date. That represents you putting your cards on the table. Showing him that you’re interested in the hope that he reciprocates in kind. Even if it takes a few days.
  13. What do you do for fun? People love to talk about themselves, so this is perfect for that purpose. Particularly men. Anyway, this way you get a natural invite to things like his sports games. While getting up early on a Saturday morning to watch him kick a ball around in the cold might not represent the most relaxing wake-up call, it will mean the world to him. It’s his way of trying to introduce you into his world, you just have to show him you’re willing. That way you can win him over.
  14. If you could go anywhere in the world, where would you go? Again, this gives you the perfect opportunity to make future plans with your crush. You can get their attention by showing common ground and by wanting to accelerate the relationship in a way that you know he’s interested in.
  15. Want to know what I think sounds like a fun date? If he isn’t getting the hint, then seize the moment. Don’t overthink it. Just go for gold and remember that the worst he can say is no. Plus, if you can’t be bothered to put yourself out there, you probably need to ask yourself questions about whether you actually like him or not.

There you have it, a few suggestions on how to flirt effectively with your crush and see where they stand. Good luck!

Hannah has a Masters degree in Romantic and Victorian literature in Scotland and spends her spare time writing anything from essays to short fiction about the life and times of the frogs in her local pond! She loves musical theatre, football, anything with potatoes, and remains a firm believer that most of the problems in this world can be solved by dancing around the kitchen to ABBA. You can find her on Instagram at @_hannahvic.