Crushes are entertaining…and terrifying. Yes, it’s completely normal to be nervous when speaking with your crush or to lose your words when trying to get to know them better. But don’t worry; that’s why I compiled this list of questions to ask your crush, compiled by experts in sex, love, and intimacy.
“Vulnerability encourages intimacy,” says Shan Boodram, a certified intimacy educator and Kentucky sex expert. “It can create a feeling of love between people who don’t know each other otherwise, even within a single conversation.” That is why Boodram advises avoiding small talk and divulging personal details to keep the conversation deep.
Furthermore, she explains, these questions to ask your crush can reveal whether or not this person is right for you. “When you ask questions, you reveal information about your values, morals, lifestyle, long-term goals, short-term goals, and more,” she explains. “These are all indicators of whether or not this person is crush-worthy for you.”
Good Questions to Ask Your Crush
Now that you understand why getting to know your crush is so important, it’s time to get down to business. Continue reading for expert-recommended questions to ask your crush.
1. Tell me about your job.
So, knowing your potential partner’s job is essential. While it may appear to be a simple question, it is an important aspect of who your crush is as a person, according to Shannon Chavez, a licensed psychologist, and sex therapist. If you don’t like their line of work, they might not be for you.
2. What is your area of interest?
Not everyone’s job is their true calling in life. This question allows you to learn more about how they would like to spend their time. According to Chavez, asking about their deepest desires will help you form a more realistic expectation of who your crush is in real life. That is quite significant.
3. What would be your ideal job?
Now that you know their job and their passion, you must follow up and inquire about their dream career. Again, Boodram emphasizes the importance of going deeper to foster intimacy.
4. What are your interests?
“Having a crush means you’re fantasizing about who this person really is,” Chavez explains. In order to get away from that fantasy, ask them questions about their hobbies. This will help you get a sense of their true selves.
5. What do you enjoy doing for fun?
If you’re going to be spending more time with them, you’ll want to know what they enjoy doing for fun, right? You can compare leisure activities, which will tell you if you’re compatible in real life.
6. How would you describe your ideal weekend?
This one is straightforward. Ideally, you spend your weekends hanging out with your crush. Do you have similar preferences when it comes to your vacation days? Once again, it’s a compatibility test!
7. Where do you live and why do you live there?
Yes, this is technically still considered small talk; however, you must first master the fundamentals before moving on to more advanced topics! It’s also beneficial to learn why they chose their neighborhood, what they like and dislike about it, and so on.
8. Do you live on your own?
So, this is a bit of a loaded question to ask your crush, but it’s still important. It will reveal if they have roommates if they can afford to live alone if they have children and other information.
9. Do you enjoy preparing meals for yourself and others?
Yes, these may appear to be surface-level questions to ask your crush, but they open the door for a deeper conversation. How did they learn to cook if they enjoy it? Did they learn from a family member? What is their house specialty? The possibilities for follow-up are limitless.
10. What is your favorite restaurant, and why is it your favorite?
According to Chavez, asking about favorites allows someone’s personality to shine through. This one also gives you two an excuse to plan a future date.
11. Who would win a space battle between a polar bear and a great white shark?
“For fun, I used to ask all the time, if a polar bear and a great white shark had to fight in space, who would win?” says Boodram. “It’s a silly question to ask your crush, but it’s also an opportunity for someone to demonstrate creative and analytical thinking.”
12. Do you ever volunteer in your community?
This question demonstrates that you are interested in how they spend their time and how they give back to the world.
13. Where would you live if you could live anywhere in the world?
“I think it’s really important to figure out what signals compatibility for you,” says Boodram. If they have to stay in your favorite city, you’ll want to know where they’d like to end up. Are you and I on the same page? That could be a problem in the future.
14. How do you envision your ideal work-life balance?
If you can’t wait for five o’clock to arrive, dating a workaholic might not be for you. It’s also beneficial to learn about their pros.
15. What is your favorite animated film, and why is it your favorite?
Isn’t this one strange? That shouldn’t be the case. “If you have kids, asking someone what their favorite animated movie is might be logical because that can help; you know if they have kids around or if they have a child-like spirit,” explains Boodram.
16. What is your all-time favorite movie, and why?
Again, this is a simple question to ask your crush, but it leads to a plethora of follow-ups. Is it about a significant issue? what relevant Is to them? Is it amusing? All of the answers to these questions will give you a sense of who this person is outside of your fantasy.
17. What is your favorite TV show, and why is it your favorite?
If you both have the same favorite show, you might be able to binge-watch it together. Or, if you know you’ll never be able to sit through nine seasons of How I Met Your Mother, perhaps you and your partner aren’t a good match.
18. What do you consider your greatest accomplishment?
“I like questions about people’s emotional experiences,” Chavez says. “It could be something you’re particularly proud of in your life, such as one of your greatest achievements.” Is there a bonus? This question allows them to brag a little bit, which means you can be impressed by their skills, whatever they may be.
19. Do you have a voter registration card?
If politics is important to you (and it should be! ), it’s time to answer this big question. It will reveal whether you and your partner share values, some of which may become a source of contention later.
20. How do you feel about your relationship with your parents?
“Find a way to avoid coming across as an interrogation while still asking the tough questions,” Boodram advises. If you’re curious about their relationship with their parents, it’s not a bad idea to ask gently.
21. Are you currently in debt?
This one can be awkward, but according to Boodram, it’s definitely fair game if the flow of the conversation is right. Because many couples eventually share their finances, you should be aware of what you’re getting yourself into.
22. What is the most extraordinary thing you’ve ever eaten?
Foodies, come together. This question invites them to share another memory, as this could be something made by their family, at a cool restaurant, with friends, or anything else.
23. What is the most decadent meal you’ve ever consumed?
More recollections! Perhaps their employer treated them to a fancy dinner, or perhaps their family used to go out on special occasions. In any case, it will give them the opportunity to tell you a story, which will help you learn more about who they are.
24. What is the most expensive gift you’ve ever purchased for yourself?
“You can also discuss life’s guilty pleasures,” says Boodram. This includes gifts, foods, vacations, and anything else you want to learn about this person.
25. What is the best vacation you’ve ever taken?
“I like to inquire about memories from crushes or new relationships,” Chavez says. “Memory evokes positive emotion, allowing one to see a person’s personality shine through a little more.” With this simple question, you can learn about their super fun backpacking trip across Europe or their relaxing AF island vacation.
26. Tell me about your most embarrassing moment.
This type of question (s) to ask your crush, unless they are uncomfortable telling you, reveals a lot about how they deal with their feelings of fear, shame, and embarrassment. Everyone has these awkward moments, so neither of you should feel bad about sharing.
27. What kinds of toys do you like to play with in your bedroom?
If you’re ready, you can always get a little more sexual with your questions. “Are you the type to take a walk on the wild side?” “Bringing up sex would be a great way to spice things up and stand out.”
28. What is your most fervent sexual fantasy?
Learn more about their desires with this odd question; as long as you believe the relationship is still there at this point. You’ll find out more about what they’re like in bed and whether you’re sexually compatible.
29. Do you have any sexual inclinations?
Yes, according to Boodram, you can go there. You can exchange kinks, and it’s a huge plus if you’re into the same things. Could you try them out later tonight?
30. How would you describe your sexual orientation?
Just so you know, your gender may not be the only one they’re interested in. Learn more about their sexuality to get to know them better.
31. Do you have a celebrity crush?
“Ask someone about their fantasies,” Boodram suggests. “Anything sexy or strange.” A fantastic way to do so? Find out who their celebrity crushes are, both past and present. It will basically give you an idea of who they are attracted to and why, which is a plus.
32. Is there anything you wouldn’t do in bed?
It’s also a good idea to set some boundaries. It’s probably best to know if anything is completely off-limits to your crush before you get physical.
33. How frequently do you experience stress?
Look, the world can be a stressful place. That means you’ll be curious about how your crush handles life’s ups and downs. Your compatibility may be off if each of your coping mechanisms clashes.
34. What was the name of your first love?
Once again, memories! Allow them to open up about their past loves, what made them special, what made them not work, and more if they are willing to talk about it. That being said, if they’re willing to share, be prepared to reciprocate!
35. What was the date of your first kiss?
Sure, depending on what else you’ve already laid out there, this one may be a little cutesy, but it can be an opportunity to share a fun or embarrassing memory from your youth with each other, which will only bring you closer together.
36. How was your first experience with sex?
This question will not only allow you to share a potentially awkward memory, but it will also reveal how your crush defines “sex.” Is it verbal? Penetration? It’s time to listen to them out.
37. What qualities do you seek in a partner?
Yes, you’ve had a crush on them for a long time, but now it’s time to get the lowdown. Are you really what they’re looking for in a partner? It may be difficult to hear at first if you don’t vibe on this level. However, it is preferable to get this done sooner rather than later.
38. What do you look for in a partner?
“I believe one of the best questions to ask your crush is what they value in a relationship,” Chavez says. “You can get a sense of where they stand in terms of their values and what’s important to them in their love life.” Hopefully, your values are also in sync.
39. Do you want to do something serious or something fun right now?
“You want to know if this person is looking for a casual friendship or a serious relationship,” Chavez says. “That way, you can set realistic expectations, knowing whether they’re committed or looking for something more casual.”
40. What is your most cherished childhood memory?
Chavez explains that this is your chance to learn about your crush’s younger self. Hopefully, their memory will reveal something about how they came to be the person they are today.
Related Articles: WHAT DOES LOVE MEAN: What It Means In A Relationship & To A Woman
Flirty Questions to Ask Your Crush
Do you spend hours online reading cute and slightly cheesy crush quotes that remind you of the person you like? In this post, I’d like to share some flirty questions to ask your crush, so you’re fully prepared when you start texting or talking to your crush in person! “Flirty Questions To Ask Your Crush” is up next.
- Do you think it’s possible to fall in love at first sight?
2. How was your first kiss?
3. Describe your best kiss.
4. What was your initial reaction to me?
5. What do you consider to be the ideal date?
6. What are the three qualities you seek in a partner?
7. What causes you to automatically swipe left on someone?
8. Have you ever felt true love?
9. If you could have a conversation with your ex, what would you ask them?
10. What is the most commonly used emojis in text messages?
11. What is the most unusual thing you’ve ever done to catch someone’s attention?
12. What is your greatest fear in terms of relationships?
13. What is the most humiliating thing you’ve ever done in front of someone you care about?
14. Do you find first dates to be enjoyable or stressful?
15. Who is your favorite movie couple, and why do you like them?
16. Where do you like to take your significant other?
17. What is your favorite relationship, and why?
18. When do you think it’s appropriate to go public with a relationship on social media?
19. Most powerful turn-on for you?
20. What is your biggest pet peeve?
What is your favorite aspect of me?
21. When was the last time you sent a flirtatious text message?
22. What is the most difficult aspect of being single?
23. What is the best part about being single?
24. Do you think you’re a hopeless romantic?
25. Would you prefer a casual or serious relationship at this point in your life?
26. What is the most difficult aspect of being in a long-term relationship?
27. Would you write your own wedding vows if you were getting married?
28. What is your biggest regret from a previous relationship, specifically?
29. How do you recover from a breakup?
30. Which meme best describes your life?
31. Do you prefer to love and lose, or to never love at all?
32. Do you start the makeup conversation after a disagreement or wait for your S.O.?
33. How many times have you said “I love you” in a romantic setting?
34. What’s the most ridiculous reason you’ve ever used to get out of date?
Questions to Ask Your Crush while Texting
When you’re texting a new special someone, it can be difficult to strike the right tone; so having some questions to ask your crush can help you steer the conversation in the right direction and encourage them to open up. It saves you the trouble of having to constantly come up with witty texts, and it basically guarantees that someone will be excited to talk to you. Almost everyone enjoys talking about themselves.
Here are some text-messaging questions to ask your crush to see if you two have the chemistry to make your connection last:
1. When Was Your Most Recent Crying Moment?
You don’t need to know why they cried; just see if they can keep up with your weekly routine.
2. How Did You Act When You Were a Kid?
Talking about how much of a jerk you both worked 99 percent of the time.
3. What is the strangest pet you’d like to have?
Forget about snakes. Let’s talk about how you fantasize about being the owner of a leech.
4. What’s Your Biggest Date Deal-Breaker?
Let’s get this out of the way: if you and your partner are completely incompatible, wouldn’t you rather know now?
5. What Is the Color of Your Aura?
Bonus points if they know not only the color but also which chakra it corresponds to.
6. What is your favorite meal you’ve ever had?
Mine is a sandwich I had in Venice in 2018.
7. What Are Your Thoughts on Free Will?
This is an excellent question for both philosophy students and astrologers.
8. What is the most flattering compliment you’ve ever received?
You’ll have a better idea of how to beat the competition once you’ve studied it. Because no one compliments as you do.
9. How Would You Survive If The World Ended?
With the end of the world looming, it’s probably a good idea to figure out if this is someone who would learn to till the land… or if they would eat you first.
10. Do You Prefer To Live In The City Or In The Woods?
My parents grew up in the woods. I was raised in the woods. I need to be with someone who is all about the city.
11. Do You Think Soulmates Exist?
I’m not sure if I believe in soulmates or if I just want to believe in them; but anyone who dismisses the concept probably doesn’t like fun, either.
12. What is your greatest fear?
Asking your crush this question naturally leads to recurring nightmares, childhood terrors, and similar subjects — just in time for Halloween.
13. Have You Ever Loved Your Best Friend?
It’s a good idea to get an answer to this question early on, especially if you’re concerned about any lingering feelings.
14. How many people do you have a crush on right now?
If you talk to someone who has five crushes a day, don’t be too disappointed. Crushes are entertaining! And that doesn’t mean they’re not interested in you.
15. What was the most difficult job you’ve ever had?
Complaining can sometimes be confused with bonding.
16. Who Do You Turn To When You’re Depressed?
Everyone needs a friend who will text 20 times in a row while panicking, then follow up four hours later with a casual “…but how r u??”
17. Who was your first crush interest?
Do you know how crushes make each other laugh? By discussing their previous crushes.
18. Do you eat things that have fallen to the floor?
It’s critical that you’re all on the same page when it comes to the 10-second rule.
19. What is the one item you would save from a burning house?
I’m talking about after their pets. Always prioritize pets.
20. Do You Get Ticklish?
If you’re hoping to get your bodies together sooner rather than later, this is the question to ask to see if it’s on.
21. What was your favorite movie as a kid?
Learning about your crush’s current likes and interests is important, but learning about their interests as a child can provide you with even more insight into who they are. Plus, there’s a good chance you’ll recognize whatever film they choose — there are only so many PG-rated films out there.
22. If You Could Have Any Superpower, What Would It Be?
This is a great question because it reveals what your crush values the most. Not to mention that it can spark a lively debate between flying and invisibility.
23. What Is Your Weirdest Habit?
It’s easy to put on rose-colored glasses when you’re first meeting someone new. Learning about your crush’s habits, especially the eccentric ones, can help you stay grounded. It also gives you the opportunity to tell them more about yourself.
24. Do You Have Any Guilty Pleasures?
Be forewarned: This question has the potential to turn the conversation into something more steamy.
25. Do you believe in astrology?
Are you really into each other if you aren’t comparing charts? In all seriousness, this can be a fun way to get to know your crush a little better — even if you don’t believe in astrology, it’s a great way to start a conversation.
Let’s take a look at Flirty Questions To Ask Your Crush While Texting
- What always brings a smile to your face?
- Who was your very first crush?
- What do you think is the cutest aspect of yourself?
- Both physically and mentally?
- What is your idea of the ideal date?
- Who or what is your go-to person or activity when you’re feeling down?
- What is something about which you are extremely passionate?
- The most thoughtful thing you’ve ever done for a girl?
- What is your go-to snack, dessert, or junk food?
- How would you react if a guy hit on a girl you like?
- What’s the first thing you notice about a woman?
- What is the worst that could happen to you on a first date?
- What is the first question you ask a girl on a first date?
- How do you know when you have a crush on a girl?
- What have you always wanted to do with your girlfriend but have never done?
- Where was the most unusual place you’ve ever kissed someone?
- What is the most enjoyable aspect of being in a relationship?
- What is the most appealing characteristic a person can have?
- Do you enjoy cuddling? Is it better to use a big spoon or a small spoon?
- What is your favorite feature of mine?
Let’s take a look at Intimate Questions To Ask Your Crush While Texting
- What’s the most corny pick-up line you’ve ever used that actually worked? Put it on me.
- What are some cute things you like to do when you’re dating someone?
- Do you believe you’d ever be open to having an open relationship?
- Have you used dating apps or websites before?
- What was the first thing that came to mind when you saw me?
- If we were stranded on a deserted island, what three items would you bring with you?
- Do you believe a guy and a girl can be friends without developing feelings for each other?
- What would you do if you could spend an entire day with your crush?
- The strangest thing you’ve ever done to attract the attention of a crush?
- What is your most powerful turn on?
- How would you know if I was right for you?
- What is your most serious flaw?
- Do you believe that men should always make the first move?
- How do you define a happy and healthy relationship?
- What would your ex-partners have to say about you if I asked?
- What would you do if someone approached you and kissed you on the lips?
- Tell me what is your unfulfilled sexual fantasy?
- What would you do if you had to choose between your best friend and your girlfriend?
- What do you recall about the first time you met me?
- How important is physical attraction in deciding whether or not to pursue a romantic relationship?
- If you could only ask me one question and I had to answer honestly, what would it be?
- What is the most important date stumbling block?
Deep Questions To Ask Your Crush Over Text
So, if you have your eye on someone, take advantage of the first opportunity to speak with them and ask them some of these questions to determine if they are right for you, followed by more bonus follow-up questions.
- Is there a song that comes to mind when you think of me?
2. What is a past mistake you made in a relationship that you don’t want to repeat?
3. What would you like us to do if we only had one more night together?
4. Who do you believe had the most influence on you as a child?
5. What is one significant difference between us that you adore?
6. Where would you be and what would you do if you could be anywhere other than where you are right now?
7. How do you know if you’ve had a good life?
8. Do you prefer to be extremely intelligent or extremely happy?
9. What advice would you give to yourself if you could go back in time?
10. What is your favorite type of music, and why do you like it?
11. What is the most emotional movie scene you’ve ever seen?
12. If you could dedicate a song to someone you care about, what would it be and why?
13. How do you know if you’ve fallen in love?
14. What is the most flattering compliment you’ve ever received?
15. Would you rather date someone attractive or intelligent?
What is the most thoughtful thing someone could do for you?
16. Would you rather find your true love or become a millionaire?
17. On which fictional character do you have the most crush?
18. What would surprise your parents to learn about you?
19. Do you think it’s possible to fall in love at first sight?
20. If you could have dinner with one deceased person, who would it be?
21. Can you tell me some random fun facts about yourself that you think I should know?
Bonus deep questions and their follow-ups for an in-depth discussion
1. What do you do to calm down when you’re angry?
Possible follow-up questions to ask your crush include: what kinds of things irritate you? How long does it usually take you to calm down after being enraged by something or someone?
2. Have you ever tried to appear cool and it backfired on you?
Follow-up questions could include: what made you think it was a good idea in the first place? What were your feelings like afterward? Did you ever give it another shot?
3. What is one rule you never break in your life?
Possible follow-up questions include: how do you react when others break this rule? Is there any scenario or situation in which you would consider breaking this rule?
4. What is the most significant bullet you’ve ever avoided at work?
Possible follow-up questions include: what about the times you didn’t escape with your life? What transpired? Have you ever made the same mistake in this area twice?
5. What is one skill or knowledge that you have never been able to master or learn?
Possible follow-up questions: do you know anyone who can do this, and how does it make you feel? Have you ever attempted to learn how to do this thing seriously?
6. What is your most impressive skill?
Possible follow-up questions include: has this skill ever come in handy at work or in life, or is it purely recreational? Have you ever met anyone who can perform this skill as well as you?
7. How do you spend the majority of your time during the day?
Possible follow-up questions: what would you do if you could spend your day doing anything? Have you ever gone a whole day without doing anything?
8. What is the one thing you know you shouldn’t be spending money on?
Possible follow-up questions include: what steps do you take to reduce your spending? Do you feel remorse for your spending? Why don’t you just enjoy the item you purchased?
9. Describe an event that completely altered the course of your life.
Do you ever wonder what might have happened if you had done something different that day? What if someone had stepped in?
10. Do you take yourself seriously?
Possible follow-up questions to ask your crush include: why don’t you have more fun? Have you ever had to deal with the consequences of not taking something seriously?
11. What is it about people that makes you go insane?
Hopefully, these questions to ask your crush have inspired you to think of some conversation starters for the next time you text or talk to your crush in person. Don’t be shy, and talk to your crush as if he or she were just another person you’d like to get to know! (Try not to put them on a pedestal.) This allows you to be more comfortable being yourself and displaying your wonderful personality.
Frequently Asked Questions
What questions should I ask my crush over text?
Here are some text-messaging questions to ask your crush to see if you two have the chemistry to make your connection last:
When Was the Last Time You Wept?
What did you look like when you were a kid?
What’s the strangest pet you’d like to have?
What’s Your Biggest Date Deal-Breaker?
How do I ask out my crush?
The simplest approach is to ask, “Do you want to go out with me?” This is the simplest and most direct method of asking your crush out. Because they are taken aback, they will either say yes or no, stammer for a minute before responding.