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233 Questions to Ask Your Crush

by eharmony Editorial Team January 6, 2026

Figuring out how to approach a crush you have on someone can feel challenging, particularly if you don’t know them well. But people often overthink it. By simply finding the questions to ask your crush, you can create the space for a more natural and vibrant conversation to blossom.

You may be looking for different ways to get closer to someone you’ve started to like or perhaps you found yourself stuck in the friend zone as your interactions have progressed, because you don’t know how to introduce a romantic dynamic to your conversations. Being a friend isn’t a bad thing. The initial questions you ask someone you like actually should be designed to foster comfort and understanding, as you both grow closer and begin to explore different aspects of each other’s lives, thoughts and dreams.

The beginning should resemble the process of making a new friend. People often stall at this stage because they’ve developed a communication style, and now, they need to change it. By introducing different things to ask your crush and widening the scope of questions that you ask, you can begin to promote mutual attraction.

This can include outright flirty, spicy or romantic questions that strongly signal your interest while keeping the interaction engaging. Whereas interesting and intimate questions encourage your crush to be more open and trusting with you, while also showing them that you think more deeply about things. It’s all about the tone you’d like to strike and the range of topics you want to begin connecting over. Here are some different approaches and examples of questions you could ask.   

Conversation starters with your crush

It’s often a good idea to start with a low-stakes and broad question, just to catch their attention and get the conversation going. The answers will likely encourage some small talk, where you get to know each other better. 

People often bash small-talk but it’s a useful fact-gathering stage for later conversations and starts laying the foundation for your overarching communication dynamic. Small talk with the right people can be quite fascinating and psychologically rewarding. A recent study showed that engaging in small talk daily improves confidence and one’s outlook on people and society in general.1

Think of a conversation as someone’s backyard pool. Using the right conversation starters with your crush is how you take the steps down into the pool’s shallow end and begin swimming over to the deep end. You can always just haphazardly cannonball into the deep end, but that can be messy and have unexpected results (which we explore later). 

Let’s look at some different ways you can break the ice and get the conversation flowing.

  1. What was the best part of your day today?
  2. Working on anything exciting lately, in or out of work?
  3. If you had a free afternoon with no obligations, how would you spend it?
  4. Have you been to any cool new spots in town (cafes, parks, etc.)?
  5. What’s your favorite way to spend the weekend?
  6. Do you enjoy coffee dates or movie nights more?
  7. What’s the last show or movie you binge-watched?
  8. Do you like pets? If so, cats, dogs, or something else?
  9. What kind of music do you listen to the most?
  10. Have you traveled anywhere exciting recently?
  11. What’s your favorite comfort food?
  12. Do you like trying new restaurants or sticking to old favorites?
  13. What’s a hobby you really enjoy?
  14. Do you prefer mornings or late nights?
A couple in the back of a car smiling and looking at a phone.

Good questions have multiple dimensions. They’re general enough that it doesn’t come across as prying, yet specific so it doesn’t sound generic. They explore someone’s inner thoughts, going comfortably beyond the surface level in a way where the answers to the questions naturally lead the conversation into deeper territory. Lastly and most importantly, they express curiosity and interest to your crush so that the nature of your conversation changes over time to foster mutual attraction and intimacy.

This may sound complicated, but it’s often just about putting a different spin on typical questions you ask your crush, so that it feels more engaging and forces the person you like to stop and think before they answer. This leads to authentic interactions that feel more special because they shake up our conversational scripts.

Good questions often naturally spring from good conversations. But a little help from your side couldn’t hurt. Here are some specific examples of how you could approach it.     

  1. What’s something that always makes you laugh?
  2. Do you prefer spontaneous plans or well-thought-out ones?
  3. What’s your favorite memory from the past year?
  4. What’s your go-to karaoke song?
  5. Do you enjoy big parties or smaller gatherings?
  6. What’s a skill you’d love to learn?
  7. What’s your favorite holiday and why?
  8. Do you like surprises or prefer knowing what’s coming?
  9. What’s the best trip you’ve ever taken?
  10. What’s your idea of a perfect day?
  11. What’s something you’re proud of but don’t get to talk about often?
  12. What do you geek out about?
  13. Are you more of a homebody or an adventurer?
  14. Who in your life inspires you the most?
  15. What’s a small thing that always makes you happy?

Romantic questions to ask your crush

Once you’ve built some solid rapport, romantic questions help change up your dynamic and start making your intentions clearer. These are the questions that help steer your interactions away from the friend zone in a way that’s less direct than flirting but still strongly indicates where your head is at when it comes to this growing relationship.

A good romantic question asks about the crush’s dating habits, their interpretation of authentic romance and how they like to approach a new relationship. They say something without saying it, which is often a more comfortable route if you’re feeling somewhat trepidant and want to feel out how they see your bond. 

This is particularly a good option if you’re trying to find better questions to ask your crush while texting, as a text message gives you some emotional distance to collect your thoughts and have more control over the message. It also doesn’t corner your crush. Instead, it gives them time to consider and answer thoughtfully. Start off with something easy and general, like these questions:

  1. What’s your idea of the perfect date night?
  2. Do you like candlelit dinners or casual dates?
  3. What’s the sweetest thing someone could do for you?
  4. Do you believe in love at first sight?
  5. What’s the most romantic movie you’ve ever seen?
  6. Do you like slow dancing, even without music?
  7. What’s the most romantic trip you could imagine?
  8. Do you enjoy receiving love notes or texts?
  9. What song feels the most romantic to you?
  10. What’s one small gesture that always melts your heart?

What is romance to a man?

Men find romance in many forms beyond these questions. Here, we explore the gestures they enjoy most and help you better understand their desires.

Serious questions to ask your crush

Serious questions start to explore deeper aspects of your crush’s personality, how they look at the world, their value system and their dreams for the future. While lighter questions and small talk can help you come across as charming and approachable (which is a good place to start), figuring out deep questions to ask your crush is how you begin to forge your unique connection.

You can actually start asking deep questions relatively early in your interactions, often towards the middle of your first conversation. One study paired participants with two different strangers, one of whom they were instructed to exchange small talk questions and another deep questions. Not only did almost every participant prefer the deeper conversation, but they also expressed greater feelings of fondness, closeness and a sense of mutual understanding for the deep talker.2

These questions can also help you figure out whether you share any deeper compatibility with your crush beyond surface infatuation. Here are a few you could try out.

  1. What do you value most in a relationship?
  2. Do you see yourself wanting kids in the future?
  3. What’s the most important lesson you’ve learned from past relationships?
  4. How important is honesty to you?
  5. Do you believe people can change in relationships?
  6. What role does family play in your life?
  7. Do you think long-distance relationships can work?
  8. What’s a deal-breaker for you in dating?
  9. What’s your definition of commitment?
  10. How do you usually handle conflict in relationships?

Smooth questions to ask your crush

You’ve gotten the conversation going and built some rapport. Perhaps you’ve even thrown in some deep or somewhat romantic questions to see how they respond, and it seems like the initial attraction and interest are mutual. Now it’s time for the charm offensive. Smooth questions tend to be bold and unabashed, not so much indicating interest as waving a giant flag with a big red heart on it.

Asking your crush smooth questions takes confidence and can be somewhat risky, but the potential rewards are significant. However, with that being said, being very smooth is often a go-for-broke strategy. It will either help your relationships surge forward or stop the interaction dead in its tracks if they’re not ready to go there. This is why these questions are much more effective in very small doses. 

Here’s how you can ask smooth questions while still sounding sincere.     

  1. What’s one thing you notice first about someone you like?
  2. Do you believe in chemistry between two people?
  3. What’s the best compliment you’ve ever received?
  4. What do you think is the most attractive trait in someone?
  5. Do you like playful teasing?
  6. What’s one thing that instantly makes someone more attractive to you?
  7. Do you think confidence is more attractive than looks?
  8. What’s the smoothest pickup line you’ve ever heard?
  9. Do you like when someone flirts with you directly?
  10. What’s something that always makes you smile?

Intimate questions to ask your crush

Intimate questions beg intimate responses. Intimate and personal questions tend to be deeper, asking your crush to be more vulnerable and open with you. This can take a bit of initial intimacy, though, so try to build a healthy rapport and perhaps even voluntarily disclose something more personal about yourself first to encourage reciprocation. 

A very important aspect of continued disclosure is how you handle their answers early on. It’s almost like a trust exercise of sorts. If you show you aren’t actively listening when they respond, don’t validate their feelings, fail to communicate any kind of empathy, or react negatively or judgmentally to their response, you’ve failed the exercise and likely spoiled any chance at future intimacy. This is often easy, though. When you really like someone, being present and kind feels natural because making them happy automatically makes you happier. This is because happiness, on a social level, is highly contagious. The closer we are to someone, the stronger the effect. This was psychologically explored in the novel The Contagious Power of Thinking.3

Let’s look at some questions to ask your crush that help promote closeness and intimacy. 

  1. What’s your love language?
  2. Do you believe emotional connection is more important than physical?
  3. What makes you feel truly cared for?
  4. Do you enjoy deep, late-night conversations?
  5. What’s the most vulnerable moment you’ve shared with someone?
  6. What’s your idea of true intimacy?
  7. When do you feel most at peace with someone?
  8. What’s one thing you’ve never told anyone else?
  9. What does ‘home’ feel like to you?
  10. What does it take for you to truly trust someone?
  11. Have you ever had your heart broken?
  12. What’s something you’ve never told anyone before?
  13. What’s a boundary that’s really important for you in a relationship?
  14. How do you show affection and how do you like to receive it?
  15. What does a safe and supportive partnership look like to you?
A woman with her arms around a man's neck, looking at a phone.

Making your crush laugh is one of the quickest routes to their heart, so try to find some fun questions to ask your crush to create that distinct bond over shared humor. We tend to perceive humorous people as being popular, extroverted, friendlier and easier to connect with.

Although studies have found that only certain types of humor are socially and mentally productive, particularly affiliative humor – jokes aimed at making the people around you laugh – and self-enhancing humor – good-natured humor that emphasizes a positive world outlook and the ability to laugh at yourself.4

While being funny can make you seem more desirable to your crush, it’s actually laughing together that distinguishes a bond between partners. This is why we suggest sending your crush funny questions, instead of trying to make them laugh with a joke. It essentially invites them to collaborate on creating a humorous conversation together. Silly questions are particularly handy when you’re struggling with what to talk about with your crush over text. Try something new instead of crafting another “Hey, how have you been doing?” message.

Simple questions often lead to really funny places. Here are a few you can try throwing out. 

  1. If you could have any superpower, what would it be?
  2. Would you rather always have to sing instead of talk or dance instead of walk?
  3. What’s the silliest thing you’ve believed as a child?
  4. Would you rather fight one giant duck or 100 duck-sized horses?
  5. What’s the weirdest food combo you secretly love?
  6. What’s the dumbest way you’ve ever injured yourself?
  7. If you had to live in a cartoon world, which one would it be?
  8. What’s your go-to funny face?
  9. Do you believe in aliens?
  10. What’s the most ridiculous fashion trend you’ve ever tried?
  11. What’s the weirdest thing you’ve ever thought about in the shower?
  12. If you could only use one meme to communicate for the rest of your life, which one is it?
  13.  What’s your favorite dad joke?
  14. If animals could talk, which would be the rudest?

Risky questions to ask your crush

Asking a risky question really puts you out there, essentially confessing your feelings to your crush without saying the exact words “I like like you.” If you’re not one for much preamble, you can feel that there’s a definite chemistry between you or you’ve decided that you’ve laid enough groundwork, in terms of getting to know them, that it’s time for that cannonball we mentioned earlier.

There’s not much to be said of its effectiveness. They’re either interested and will say yes, or they’re not, and therefore it’s a no. It’s closure, of sorts, because it removes all ambiguity. It makes your feelings clear to your crush and asks them to make a decision, but in a way that isn’t aggressive or feels like it’s coming entirely out of left field.

However, it’s important to keep the risky questions that you ask your crush simple. Don’t bombard them with context and caveats along with the question. Here are some basic but effective examples.  

  1. Have you ever had a crush on someone unexpected?
  2. Do you think of me as just a friend or something more?
  3. What’s the boldest thing you’ve done when dating?
  4. Have you ever been in love before?
  5. Would you ever date someone completely opposite to you?
  6. What’s your biggest dating fear?
  7. Do you believe in taking risks for love?
  8. Have you communicated your feelings to a date first?
  9. How have you asked someone to be your partner in the past?
  10. Are you seeing anyone right now?
  11. What do you think of me?
  12. Have you ever thought about what it would be like if we were more than friends?
  13. What’s your biggest deal-breaker in a relationship?
  14. What’s the reason you’re single?
  15. Am I your type?

How to ask someone out on a date: A practical guide

Find out how to ask someone out with confidence. Learn the best strategies for approach, handling different mediums and your fear of asking someone out.

How to ask someone out over text

Ever wanted to know how to ask someone out over text? Explore dos and don’ts, message styles and different approaches for asking someone out over text.

Flirty questions to ask your crush

Flirty questions are a bit like romantic and risky questions – in that they convey your feelings to the person you like – but they tend to be more playful and low-pressure. Flirty questions instead create romantic tension and more humorously explore the idea of moving the conversation forward, beyond friendship or basic acquaintance. These questions also don’t put the person you like on the spot. Flirting is more non-committal, allowing them to explore a romantic dynamic with you without necessarily agreeing to date you, right now.   

Asking your crush flirty questions is effective when you find that the conversation is stuck on small talk or when your interactions are getting deeper, but you just need to give it that final push to place your communications firmly into romantic territory.   

You can also use flirty questions to take the plunge and ask them out, but in a way that’s disarming and encourages them to give a more authentic answer. Let’s take a look at a few approaches you could try.

  1. Do you like compliments, or do they make you shy?
  2. What’s one trait you find irresistible in someone?
  3. Do you like when someone makes the first move?
  4. What’s the most fun you’ve had on a date?
  5. Do you like surprises from someone you like?
  6. What’s the cutest thing someone has done for you?
  7. Would you rather cuddles or kisses?
  8. So, are you going to ask me out, or should I just keep waiting?
  9. What’s your biggest turn-on?
  10. Do you have a favorite feature of yours? Mine is your smile.
  11. What are you doing this weekend? Besides thinking about me, I mean.
  12. Are you always this cute or is it just for me?
  13. What would you say if I told you I’ve been thinking about you?

Dirty questions to ask your crush

Texting someone a dirty question definitely is up there, in terms of risk. It’s likely not something you’re going to ask during your first few interactions (unless the sexual chemistry between you is palpable).

These questions would be considered to be in the category of sexting, so it’s probably only something you’d explore if you’ve already done quite a lot of flirting back and forth, the mutual attraction feels like a given, your conversations have already touched on somewhat dirty topics or if you’ve already gone out on a date and communicated your sexual intentions.

These can be effective questions to ask your crush when you want to get them thinking of you in a certain way and turn up the heat on the sexual tension that’s already there. However, be warned, this will only speak to the sexual nature of your relationship, not true intimacy. So if you’re going to use them to build the relationship, you should mix them in with other types of questions. Here’s how you can get that dynamic started.

  1. Do you like taking the lead or letting someone else?
  2. What’s the most daring thing you’ve done iwhen dating?
  3. Do you think physical chemistry is important right away?
  4. What’s something you find secretly attractive?
  5. Would you ever go skinny-dipping?
  6. Do you like gentle or passionate affection more?
  7. What’s a guilty pleasure you’ve never admitted?
  8. Do you like whispering secrets in someone’s ear?
  9. Would you ever kiss on the first date?
  10. What’s your favorite type of physical affection?
  11. What are you wearing right now?
  12. What’s a fantasy you’ve always had?
  13. Where’s the most adventurous place you’ve ever had sex?

Spicy questions to ask your crush

For when you want to split the difference between a flirty and a dirty question. Finding some good spicy questions to ask your crush lets ramp up how you two flirt and introduces sexuality into your interaction without being as forward or putting it all out there, the way a dirty question does. This is often a less intense option if you want to see how your crush approaches sexuality but with a question that’s more suggestively sexy thanoutright lewd. A Drexel University study found that just over 40% of casual relationships engage in actual sexting.5

So spicy questions fit better with social expectations and are therefore statistically a safer bet. It’s particularly a good option for when you’re thinking about how to talk with your crush over text after you two have already admitted your feelings for each other and perhaps even had a date or two but you’re not sure where to go from there. 

They also come across as less shallow, exploring sexuality in your crush as an aspect of them rather than simply isolating sex as the topic.

  1. What’s the most adventurous date idea you’d try?
  2. Would you ever send a bold text to someone you like?
  3. What’s something you find surprisingly attractive?
  4. Do you like a little mystery in dating?
  5. Would you ever go on a spontaneous trip with someone you like?
  6. Do you think being bold makes dating more exciting?
  7. Are you a good kisser?
  8. What’s something you find incredibly sexy that most people don’t?
  9. What’s one of your fantasies?

Interesting questions to ask your crush

Joking, flirty and small talk questions help make your interactions feel more familiar and enjoyable. But coming up with interesting questions to ask your crush, and the answers they evoke, make a conversation memorable, fostering intimacy and a more profound sense of closeness.

These questions ask your crush to be somewhat vulnerable, though, which you can encourage by being vulnerable first, by discussing a very personal or interesting story of your own, and by reacting empathetically and without judgment when they share.   

You can use them relatively soon in your interactions because they positively express interest in what makes your crush tick, their values, the things they think about and how they engage with the world. They do this while hinting towards, but not outright admitting, your romantic feelings.

Asking the right interesting question, one that’s compelling and unique, also takes the conversation deeper and makes it more entertaining for your crush, making them more likely to initiate contact in the future.

Look at these interesting question examples to get some inspiration for yours.

  1. What’s a random skill you have that surprises people?
  2. Do you believe people meet for a reason or by chance?
  3. What’s the most inspiring thing you’ve experienced?
  4. What’s a passion project you’d love to pursue?
  5. Do you think dreams tell us something deeper?
  6. What’s a place you’ve always wanted to visit?
  7. What’s a belief you’ve changed over time?
  8. What’s the most fascinating story you’ve heard?
  9. What’s one question you wish people would ask you more?
  10. What’s an unpopular opinion you’ll defend to the death?
  11. If you could have dinner with any three people, living or dead, who would they be?
  12. What’s a book, movie, or song that changed your life?
  13. What’s a belief you used to hold strongly that you’ve since changed your mind about?
  14. If you could know the absolute truth to one question, what would you ask?
  15. What’s the best piece of advice you’ve ever been given?

Unexpected questions to ask your crush

These tend to be quirky and unique questions that, ideally, your crush has never been asked before. Questions that can feel random but also fun to answer because they compel people to really process what they were asked and give answers that inadvertently reveal hidden aspects of them. 

By coming up with some random questions to ask your crush, you help create a more distinct and indelible notion of you in their memory and the interactions you have, naturally creating positive anticipation whenever you make contact. This is just how our brains work. Several studies have confirmed this6 but it’s just common sense. For instance, you probably can’t tell one day at work apart from another until you have a workday where something unexpected happens. 

Memory also has an incredibly important function in intimacy, where thinking of memories we enjoyed increases our fondness for the people we shared those experiences with.7

You can start creating these experiences by trying these examples.

  1. If you could wake up anywhere tomorrow, where would it be?
  2. What’s the strangest compliment you’ve ever gotten?
  3. Would you rather explore space or the deep ocean?
  4. If you had to give a TED talk on something, what would it be?
  5. What’s the weirdest dream you’ve had?
  6. Would you rather always be 10 minutes early or 20 minutes late?
  7. If you could live in another era, which one would you choose?
  8. What’s a quirky talent you have?
  9. Would you rather trade lives with a celebrity or a fictional character?
  10. What’s the most random adventure you’ve ever had?
  11. If you were a flavor of ice cream, what would you be and why?
  12. What’s the weirdest fact you know?
  13. Do you believe in any conspiracy theories?
  14. If you had a personal theme song that played when you entered a room, what would it be?
  15. Which fictional world would you most like to live in?
  16. Is a hot dog a sandwich? Settle this for me.

Questions to ask your guy crush

You may be wondering if you should approach questions to ask a guy differently from women. From a content perspective, not as much as you’d think. Men show a general tendency toward exterior topics like challenges they’ve faced, personal stories and perspectives on the future. While men aren’t very emotional with their friends, they tend to erect less restrictive boundaries with prospective romantic partners. So you can use almost all of the questions we’ve mentioned for any gender. If anything, men tend to be easier to attract. Studies have shown that they’re more sensitive to flirting and courtship cues because, on a perceptual and cognitive level, guys perceive missing these cues as a more costly mistake than women do.8

So, feel free to ask your guy crush the questions that interest you, as they’re more likely to respond positively to any perceived interest in them. If you don’t know where to start, try one of these. 

  1. What’s something you feel like you’re good at?
  2. What’s your favorite sport?
  3. Do you enjoy gaming or watching movies more?
  4. What’s your favorite type of music?
  5. Do you prefer hanging out with a group or one-on-one?
  6. What’s your go-to snack while watching TV?
  7. Do you like surprises from someone you’re dating?
  8. What’s your ideal weekend plan?
  9. Do you enjoy cooking or prefer ordering in?
  10. What’s one thing you always wanted to try but haven’t?
  11. What’s the best advice you’ve ever received?
  12. What’s the most adventurous thing you want to do in your life?
  13. How do you and your friends usually hang out?
  14. What’s a challenge you overcame that made you a better person?
  15. What does a “successful life” look like to you?
  16. What’s a movie that every guy should watch?

Questions to ask your girl crush

Does the fact that guys are more sensitive to when questions are flirtatious mean you have to make romantic interest more obvious with the questions you ask a girl? This would only be true if the opportunities to interact with your crush are very limited.  

Otherwise, we’d say being overly obvious might come across too strongly. Just by showing consistent and distinct interest in initiating contact and finding out more about a woman you have a crush on will be more than enough for her to pick up that you’re hoping for something more than a platonic connection.

Try one of these to get things going.      

  1. What’s your favorite type of date?
  2. Do you like sweet gestures or adventurous surprises?
  3. What’s your favorite dessert?
  4. Do you enjoy going out or staying in more?
  5. What’s your go-to song when you’re in a good mood?
  6. Do you like romantic comedies or thrillers more?
  7. What’s a small thing that makes you feel special?
  8. Do you prefer cozy nights or fun outings?
  9. What’s your favorite way to relax after a long day?
  10. Do you like receiving compliments often?
  11. What’s something that can instantly make you laugh?
  12. Who is the most important woman in your life and what has she taught you?
  13. What’s the best compliment someone could give you?
  14. What is a simple pleasure you absolutely love?
  15. What’s your favorite memory from a trip you’ve taken?
  16. What’s a quality you really admire in other people?

Questions to ask your crush to see if they like you

If you’ve decided you’re going to firmly test the waters and find out just how they feel about you, certain questions can help you gauge their interest levels. These are generally the kinds of questions you ask your crush that relate directly to their current love life and dating situation. So, regardless of how subtle you try to make them, they are going to telegraph what you’re getting at.

This isn’t a bad thing, though. Your crush should be at least somewhat aware of your interest. Otherwise, you’re being far too subtle. A lot of the examples we’ve included are designed as much to help reveal certain important aspects of your crush to establish compatibility as they are to convey a deeper, more intense and healthily grounded interest in someone you like.

So, you should start to ask the kinds of questions we’ve included below when you’re starting to get ready to ask them out, but you just want to establish whether it’s even an option to begin with.   

  1. Do you think we have good chemistry?
  2. What was your first impression of me?
  3. Do you enjoy spending time with me?
  4. Would you want to go on another date with me?
  5. What’s something you like about me?
  6. Do you find yourself smiling when we talk?
  7. Would you introduce me to your friends?
  8. Do you like when I text you randomly?
  9. What’s something we could do together that you’d enjoy?
  10. Do you think we’d make a good couple?
  11. So, what do you look for in a partner?
  12. Are you dating or talking to anyone right now?
  13. A friend and I were talking about types—what’s your type?
  14. What do you think our dynamic is like?
  15. Would you be open to someone asking you out right now?
  16. I was thinking of going to [event/place] this weekend. Any interest in joining me?

Does she like me?

Have you ever wondered if she has feelings for you? Find out how to tell if she thinks of you that way and look out for the signs.

Does he like me?

Are you wondering whether he likes you? Here are some signs that he’s interested and ways to figure him out.

Yes or no questions to ask your crush

While we often offer the general dating tip to ask open-ended questions when you’re trying to create conversation, some really important pieces of information about your crush are also hiding behind yes or no questions.

We’ve already included some of the most crucial questions to ask your crush, such as “Are you dating anyone right now?” but even more general questions are allowed to be yes or no, as long as they act as a prompt to invite more open-ended questions as a follow-up.

With closed-ended questions, always consider where they logically resolve. For instance, with the above question about whether they’re single or not. What’s your plan if they say yes, they are? It either has to be asking them out or you’re left with an obvious fake-out like “Oh, cool, I was just wondering.”

But you can still have fun with these questions, like with these examples.    

  1. Do you own any pets?
  2. Do you believe in soulmates as a concept?
  3. Does pineapple have any business being on a pizza?
  4. Are you superstitious?
  5. Would you ever go skydiving?
  6. Have you ever had a premonition come true?   
  7. Do you believe in love at first sight?
  8. Would you ever go on a spontaneous trip with someone you like?
  9. Do you enjoy texting more than calling?
  10. Would you kiss someone on the first date?
  11. Do you believe opposites attract?
  12. Would you ever date someone completely different from you?
  13. Do you like surprises?
  14. Would you call yourself more romantic than practical?
  15. Do you think physical attraction matters as much as emotional connection?
  16. What’s your ideal first date?

How to start a conversation with your crush?

Starting a conversation with your crush can feel intimidating, but keeping it simple, genuine, and context-based makes breaking the ice much easier.

  • If you’re trying to find different conversations to have with your crush and you already have a somewhat friendly relationship, try one of the conversation starters above.
  • If not, we advise starting with “Hi” or “Hey”, your name, remind them how they know you and then immediately following it up with your reason for contacting them. 
  • For instance, “Hi David, this is Hailey. We met through Jessica over the weekend at that gin bar. I just wanted to say it was really cool chatting with you. I thought I’d drop you a message so that you have my number too and also just to say ‘hi’, I guess.” This is friendly, specific, shows interest, and isn’t a complex message.
  • If their response seems receptive, ask a context-specific question that relates to anything you know about them, or they told you. This is how you first connect over an interest and get the ball rolling.
  • Ask questions, but make sure they’re also asking questions back. If not, they may not be interested.
  • Don’t over-text in the first conversation. You want to create interest and leave them wanting more. You’ve just taken the first step in establishing your new communication dynamic.
  • Repeat the last two steps semi-regularly or wait for them to contact you to establish rapport.

What to talk about with your crush?

Something that can really help inform the kinds of questions you ask is figuring out the general topics to talk about with your crush that will engage them while giving you a greater perspective of their life. Here are some topics you could start with.

  • How they fill their free time – This can be hobbies and interests, which is always a rich source of conversation, or you can expand it to deeper things like their relationships with their friends and family, media consumption habits or even passions they hope to pursue in the future.
  • Common ground – Like draws to like, as they say. Commonality is often where you’ll naturally start when finding things to talk about with your crush. This is because you can both exchange on the topic with similar levels of proficiency, making the conversation feel more effortless.
  • Travel plans – It’s almost universal that people want to see more of the world than they currently have.  But travel plans also speak to someone’s priorities in life, their values, lifestyle and what they consider culturally rewarding. For instance, people who want to travel to Ibiza versus Paris.

When it comes to what to talk about with your crush over text, the above is still fertile ground for text chats but you should also explore more nuanced aspects like their sense of humor – by sending them a funny GIF, for example – or even play a text game where you compare hypothetical situations.

How to get your crush to like you?

Winning over your crush isn’t about grand gestures. It’s about showing genuine interest, building trust, and letting your best self shine through in every interaction.

  • If you really want to make her fall in love with you, be a source of joy to them. Contacting you should be the highlight of their day. Plan exciting things if you meet up as friends, make them laugh when they’re down and always express empathy so they feel like you’re someone they can turn to on the best and worst days.
  • Always be your authentic self and practice the same honesty with them. You’re in the trust building phase, at this point, and lying or misrepresenting yourself has definitive consequences on that process.
  • When you meet up face-to-face, always be fully present and open. Listen actively and interact critically with the things they say, maintain eye contact, mirror them, keep your posture open and relaxed, and ask your crush thoughtful questions, expressing the idea that you truly see them.
  • Dress up for them. Just them seeing you trying to impress them can already foster warm feelings but looking your best can also make you seem like a more high-value partner.
  • Don’t be too available. It’s okay and even advisable to miss the odd phone call or not have every text exchange turn into an hour-long conversation. You want to indicate that you have a full life of your own and that getting more from you requires them to give more too. Having said that, don’t play hard to get either. It’s insincere and frustrating. 

How to make your crush fall for you?

Getting your crush to fall for you is all about deepening connection, creating meaningful moments, and showing genuine care in ways that feel natural and sincere.

  • The steps for how to make him fall in love with you aren’t that different from women, so use all the previous tips for girl crushes in addition to these. 
  • But as we mentioned, making your feelings obvious to men often creates a similar attraction in them, if there’s chemistry.
  • Be a safe space for him. Pew Research found men are less likely to share emotional aspects of themselves with their friends and family, instead turning to romantic partners for emotional support.9 This may not be the case with your crush, but being someone he trusts enough to confide in is a great sign, regardless. 
  • Think of questions to ask your crush that speak directly to how well you’re getting to know the real them. This is why active listening can help anyone forge better relationships. 
  • Create experiences together that are distinct and exciting. When they look back on their fondest recent memories and you’re in most of them, they’ll start to associate you with fun and adventure. This is also how you begin building common narratives and a pattern of shared laughter, which has a profound effect on bonding.

How to differentiate infatuation and love?

Infatuation says:

I love them because they’re perfect.

Love says:

I love them for who they are.

From the outset, it’s quite logical. How can you love someone for who they are if you don’t actually know who they are? Love is realistic and grounded, while infatuation is idealized and fantastical. Infatuation drives us to affection while love steers us to true understanding. Infatuation is quite fragile and can change quickly, but it doesn’t change the emotions involved. A failed infatuation can still break your heart even if it is a distinctly worse bet than real love. This is why you have to also take on board exterior opinions of your relationships and whether you’re being unrealistic.   

Infatuation is built mostly on chemicals, while love actually has an emotional foundation. In this sense, love is almost a material thing you can explain, as you recall your shared experiences and moments of authentic intimacy. Love shores up these extreme chemicals in your brain with a genuine shared emotion, so that our feelings are both reasonable for your level of closeness and have the long-term stability that infatuation inherently lacks.

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