Getting to know someone can take time but it doesn’t have to. Knowing your standards and what you’re looking for and asking the right questions can help.

On a scale of one to ten, making the effort to know your crush better hovers somewhere around a 20. Sure, Instagram has informed you that they like long walks during the summer, and their Twitter is filled with all their favorite bands — but what really gets them ticking? 

Do they prefer adding cereal before milk? Have they ever been to a nude beach? What’s their life philosophy, or the craziest thing they ever did while traveling? Is there such a thing as a perfect date? How do they define love, and what is their history with long term relationships? 

When considering questions to ask your crush, the last thing you want to do is make them feel awkward or like they’re at a job interview. Finding the right balance between a game of 21 questions and a friendly, light-hearted conversation is usually ideal. This way, you’ll learn more than their favorite childhood memory or their last relationship – you’ll get an idea about whether or not that special person likes you back! 

We’ve selected a number of questions with very specific agendas to help you know your crush better. These questions will range from silly trivia to deep questions that will give you a better idea of their way of thinking. They may also help with forming a connection. We’ve also included a few good questions to ask your crush to determine how they feel about you.

But before we get ahead of ourselves, there’s one thing you may need a little help with: how to get them talking in the first place!

How to Start a Conversation With Your Crush: Your First Impression is Important

Making the leap from watching your crush go about their day at work, school, or the gym to actually pulling them aside for a chat can be a very scary task. But spoiler alert: for all new relationships – even friendly ones, it’s a necessary step.

When it comes to questions to ask your crush, you might be worried: What happens if they aren’t interested in speaking? Will they roll their eyes if you catch them at a bad time? What if your voice suddenly cracks mid sentence? It can be unnerving. 

To ease the pressure, here’s a foolproof approach to starting a conversation with your crush. 

Relax before reaching out to your crush

Even though you’re probably super nervous and struggling to keep your voice at a reasonable pitch, your crush doesn’t need to know all that. Present a picture of relaxed calmness by first taking the time to cool yourself — and perhaps your sweaty palms, before reaching out. 

After taking a few calming breaths, it might be a good idea to practice what you plan to say to avoid stuttering over your words. It will also keep you better prepared for whatever they might throw in response.

Pick the right time to pull them aside

The most important thing to do to reduce the risk of any awkwardness or the inconvenience of having too little time to speak, it’s important to strike up a conversation with your crush at a time that works best for them. 

This means avoiding any interruptions on their commute to the bathroom, class, or what might be an important meeting. Instead, look out for downtime around lunch break or the end of work when they have less pressing matters to deal with. 

To have a lasting first impression on your crush, it’s important to plan for a time that allows for at least a few minutes of conversation.

Use something from your surroundings to spark a conversation

If your crush is unfamiliar with you, you can begin conversing by making quick introductions. If after introductions are made, there’s a little uncertainty about how to carry on speaking, you can use something around you as a prop. 

Did you both survive a grueling session at SoulCycle? Make a light-hearted joke about keeping your exercise to four-wheelers next time, or make a casual remark about the end of the school/workday. Icebreakers don’t have to be profound, but they should be interesting enough to arrest, and hopefully keep the attention of your crush.

Be casual and speak like you already know them

When speaking with your crush, you want to avoid sounding clumsy, bossy, or even uninterested in an attempt to play things cool. An easy hack when speaking is to talk to your crush as if they’re your friend, or at least a casual acquaintance you get along with.

This means adopting the same kind of speech patterns you’d use on a friend: ‘hey’, instead of ‘greetings’, likewise, avoiding strictly technical issues like work deliverables, or relatively obscure topics like the economy in Paraguay.

Ask about something you know they’re working on

Depending on the flow of the conversation and how much knowledge you have about your crush, you can extend the conversation by bringing up a non-personal project they may be working on. You could ask how they’re coming along with their fitness goals, possible work deadlines, or an important upcoming test.

In exchange, you can also contribute something similar you’re working on, or provide some light insight or comments on whatever answer they present.

Ask about something you’re certain they’ll have an opinion on

Again, if you’ve done your research, and you probably have — you can steer the conversation seamlessly to a topic they may have vested interests in. Comment about how you can’t wait for the weather to change so you can finally enjoy some time in the sun, or drop a casual remark about a band, food, location, or another thing that could excite your crush into a longer speaking time.

Following a hopefully memorable first impression, you can keep your memory fresh with your crush by saying hello when you happen to cross paths. In subsequent run-ins with your crush, you may exchange telephone numbers and social media pages to stay in touch. This helps to set the stage for questions that can help with getting to know them better.

Good Questions to Ask Your Crush: Getting to Know Them Better

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It can feel a tad overwhelming when deciding where to begin on your quest to get to know your crush. Here are some questions you can ask; conversation starters that can help build familiarity.

What do you look out for the most in a friend?

This sets a very innocent tone for associating with your crush. It’s harmless enough to show your interest in a possible companionship, while also allowing you direct information about what they prioritize in those closest to them.

By learning what your crush looks out for in a friend, you can also learn important things about their values. Do they place a premium on loyalty? Are they big on people around them showing spontaneity with adventures? This question could be an eye-opener as to how compatible both of you may be.

What’s a “bad” TV show you absolutely love?

A fun ice-breaker — this question not only lets you peep into the kind of shenanigans your crush gets into in their downtime, it by default, always demands an explanation. This allows for a longer conversation, with the possibility of linking to other unlikely interests they may hold.

What’s the perfect way to eat cereal?

Equal parts a get to know you question, as well as a test of personality —  this question lets you know whether or not your crush will be cool to hang out with on the breakfast table. You’re also giving them the opportunity to use their sense of humor.

Who is your celebrity crush?

So you’ll want to ask this question first to have an understanding of what they look out for in physical attributes. And secondly, you can get an idea of the traits your crush looks out for when pursuing romantic feelings, based on what it is they like about their celebrity loves.

What is your zodiac sign?

If you take zodiac signs seriously, this is going to be one of the most important questions you’re going to want to ask. Test out your compatibility with your crush — if the stars are aligned and you’re feeling extra flirty, you may pass a comment about how well your signs go together

What’s the one thing you can always talk about with no preparation?

This is a loaded question that not only lets you know what your crush is interested in, but also comes with the added benefit of watching them be cute while explaining this topic passionately for minutes on end.

What’s the best compliment you never get tired of hearing?

While you may think every part of your crush is dipped in gold and glitter, use this question to hear straight from the horse’s mouth, what their best features are and what they love being praised for the most.

If you could have one superpower, what would it be and why x-ray vision?

Because, why not?!

Deeper Questions to Ask Your Crush

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The aim of these questions is to take things a few steps further in the process of getting to know your crush. These may require a level of emotional intimacy, so you’ll want to make sure your crush is comfortable enough around you to freely answer these questions without any holdbacks. They include inquiries such as:

What happened the last time you cried?

Sharing a source of pain isn’t easy, so you’re certain to have crossed a threshold of closeness if you ask and your crush answers this question. Be sure to stay gentle with this line of questioning — take cues where they are open to speaking more or would prefer to stay quiet on a certain subject.

Describe your most vivid childhood memory

Watch them light up as they recall a time and space entirely different from how you view them now.

How different is your life from what you imagined it would be when you were younger?

Dig deeper into their youth, and learn more about their previous expectations and how much it differs, or is the same with their present.

What’s the first thing on your bucket list?

Use this question to find out not only how adventurous your crush is willing to be, but to also segue into their thoughts on death and the afterlife.  

What would you pursue if money was no object?

Would they start a dog orphanage or head into professional juggling? Learn about the wildest aspirations your crush may have with this question, and feel free to share your most audacious plans as well.

What was something that terrified you, but you did anyway?

A very vulnerable ask, they may hesitate to share this, but feel free to encourage them by sharing a similar moment of your own.

Get into a random moment in your life that changed your trajectory completely

This may require some thought from your crush, so be a little patient while they try to figure it out. Where you can, offer some useful guidance to help them to the answer.

Things to Ask Your Crush to Know How They Feel About Love

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Not to get ahead of ourselves, but you definitely want to put feelers out to get an idea of how romantically compatible you and your crush may be. Before venturing into these questions, however, you must have established a relationship with your crush that encourages them to speak openly about love and past relationships with you.

In best-case scenarios, you may have already exchanged a few flirty questions, so these additions can help with continuing the conversation, and maybe even move you on your way to a first date!

How old were you when you had your first kiss?

A harmless introduction into their love life, make the moment even more enjoyable by also sharing your first kiss and the events that followed shortly after.

Have you ever been in a long-term relationship?

This may give you a feel for how your crush enjoys longevity in relationships. Using your discretion, prod deeper into what they think may have contributed to its length, and find out what they enjoyed the most about their union. You could possibly learn a few things about keeping the interest of your crush for a long period of time.

Describe your idea of a healthy relationship.

Another good question to ask your crush if you’re looking at a future with them. What do they hope for when starting a relationship? What’s their idea of an unhealthy partnering? Use their responses to find out more about their preferences when partnering. 

What is the most romantic thing anyone has ever done for you?

Don’t feel any pressure from this question, but instead use it as a guide to the love language your crush loves spoken to them. You may also use this opportunity to find out what they’ve done that most deeply resonated with a former partner.

What is the biggest deal breaker, things you won’t accept in a new relationship?

Keep your pen to paper with this question, and listen carefully for anything that you may be guilty of with their answer. 

Will you ever make the first move if you have feelings for a person?

If you’re feeling extra spunky, get a quick feel for how your crush fares in the bravery department. Fingers crossed, they’re open to making the first move, but if their response says otherwise — you may need to muster up the courage to find out how they feel directly.

Does My Crush Like Me?

To wrap up, while you’re asking all these questions to know your crush better, it’s important to keep an ear out for certain inquiries they might throw your way. In some cases, your crush is sending you clear signals that they may be interested in a relationship with you, and are equally on a fact-finding mission. 
Look out for questions about your relationship status, food preferences, life goals — you know, the kind of questions you’d ask them. Their body language, the speed of their responses, as well as increased laughter when you’re around them are also easy ways to determine whether your crush is also crushing on you. No matter what happens, have fun and be confident!

You can find even more questions right here on Goalcast. And once you and your crush start building a relationship, be sure to check out our piece on questions to ask your boyfriend or girlfriend.