30 Bold and Thoughtful Questions To Ask Your Crush

Finding true love can be stressful on so many levels; for a lot of people, the fear of being rejected has kept them away from even trying, just as some simply don’t know how to talk to someone they are crushing on. It is not hard to see why talking to your crush seems to be very tasking. You want to make a good and lasting impression, so it is only natural that you have spent a great deal of time replaying how things could play out in your head. Though it might look like pigs would fly before you have that perfect conversation you have always imagined with the special someone, there are questions to ask your crush that can facilitate a deep conversation.

Fun and interesting questions are great conversation starters on any day. Moreso, they go a long way in helping you keep the conversation going without awkward silences. So, if you really want to take things up with your crush, you would find the questions discussed here very helpful in coming up with your own unique questions. Nonetheless, the first play on the card is to be nice and warm to your crush and the people around him/her. This would lay the foundation for a smooth conversation when you eventually find the perfect time to talk to the person.

While waiting for the right time, learn about the things they like, what they are passionate about, their perception of the world around them, and what have you. All of these can be incredibly useful for generating questions tailored towards getting your crush to feel comfortable around you. With that, you would have a better chance of expressing your feelings and of course, a step closer to landing the lover of your dreams.

Questions To Ask Your Female Crush To Learn More About Them 

When you get the chance to initiate a conversation with someone you have secretly admired for a while, go all out for it but be sure you are prepared and wouldn’t come across as desperate. To have your mind in the right place, think of it as an opportunity to make a new friend. You can kick off the conversation with an impersonal but interesting question that would soon have the person sharing her biographical information with you. Mind you, things could quickly get awkward if you ask a question you can’t naturally follow up, such that a mere “yes” or “no” answer can put to rest. Below are some examples:

1. If you had the chance to choose where you were born, where would it be?

This question is an intriguing alternative to the usual “where are you from?”. It does more than just providing information about a person’s place of birth and hometown. It is a gateway to learning about your crush’s upbringing and childhood experiences. She might end up sharing stories about their early life that are dear to her heart. This would only have the person feeling close and comfortable talking with you. The question can also provide useful insight into how your crush thinks and how they see things. Through it, you might realize you don’t really want to date them. With this question, you would find that there are many other natural conversation paths to pursue.

2. You have quite a unique life view, what did you study in college?

What someone studied can tell a lot about them and some people need to have romantic partners that are college-educated. As such, it might be necessary to ask this question. If so, it must be done in a manner that isn’t formal. Remember, it is not a business conversation: the goal is to endear yourself to your crush. Through this question, you can easily further the conversation and learn about what the person does for a living.

3. What would you be doing if you weren’t a teacher/nurse/chef?

You don’t have to be certain what the person does for a living before you ask this question. YES, you can assume whatever career you want but be certain it comes off as a compliment rather than insulting. Through this question, you can learn about the dreams and aspirations of your crush, the disappointments they have faced in life, and what they have achieved. You would realize when you ask her this question that there are many things to talk about all of a sudden.

4. What has taught you the biggest life lesson?

More than being one of the fun questions you can ask your crush, this question, like the first three, is an opportunity to get to know more about the person you have been admiring secretly. It is an effective question to ask if you want her to share her life experiences with you. The question would most likely be thrown back at you, so be ready to answer it meaningfully and sincerely.

5. What is the one thing you have done you would want everyone to try?

This is an enthralling question that might have you asking your crush out before you realize what’s happening. It creates the moment for her to tell you about how she spends her leisure time and the fun things she has always hoped to do someday. Let’s assume she expresses a desire to embark on any outdoor activities, you can capitalize on that and invite her to any of such recreation.

6. Do you think there is really life after death?

When you are crushing on someone, it’s most likely you don’t know who they are. The intense infatuation you have been feeling might evaporate with the realization that she is not compatible with you. A fascinating inquiry like this presents the ticket to explore the mind of your crush in terms of their values, beliefs, religious views, and whatnot. These factors are meaningful things to consider if you are committed to pursuing a romantic relationship with her.

7. What do you think being queer is like for people?

For a lady crushing on a lady, this question might help you learn if your crush is open to having relationships that are not heterosexual. But then, she would likely see through the essence of this question. So you might as well be upfront with it, or carefully stir your conversation towards the aspect before asking the questions.

Subtle Questions for Expressing Your Intentions to Your Female Crush

If you feel attracted to a girl and talking to her becomes a big deal, then it is only natural you might not find the right words to express your feelings even after establishing an acquaintance with the person. But with some riveting questions that sustain a conversation, you can hint at your intentions and even make them clear. This way, you buy some time to know her more and get comfortable around her pending the time you would explicitly express your feelings and what you want from her.

8. How would you know someone is into you?

This is probably the most effective of all questions to ask your crush if you suspect they are also attracted to you. It might mark the beginning of a relationship between you and her if she really fancies you. It’s a shot at confirming if the two of you have chemistry.

9. What do you find most attractive in people?

Like the question above, this is also a way of letting a girl you are crushing on express how she feels about you if you suspect she’s also crushing on you. Listen carefully to what she would say and don’t be surprised if she talks about some turn-offs that seem to describe you, especially if you have known each other for a while.

10. What is the most pleasant thing someone can do for you?

Depending on her response, you should know if she is someone you want to commit to or someone to casually date. The response of people who are ready for a serious relationship typically has some level of depth; those looking forward to having fun without much commitment would give a shallow and materialistic answer.

11. If you must dedicate a song to me, what would it be? 

Songs have always been a means through which people find expression for their inner feelings. So it’s possible the song she names would provide insight into the way she feels about you. If you feel the need, you can ask her why she picked the song. There would be a lot to talk about thereafter if you have been struggling to keep the conversation going.

12. How can someone who likes you add value to your life?

One of the most powerful questions to ask your crush, this question is an engaging way of conveying how much you want to make a meaningful contribution in her life. For many people, there is nothing as appealing as someone who is not only interested in being with them but also willing to support and push forward their life goals.

It would be hard for her to not take you seriously after this. But remember that words must be backed with actions, so there is no point asking this if you are not really interested in being a supportive partner. You would be regarded as a manipulator at the end of it all.

13. When you are having a bad day, what is the one thing that can turn things around? 

A strong bond can emanate between you and her through this. Although it doesn’t seem like it, her answer would be letting you in on something she might not have shared with anyone. As such, her mind is immediately tricked into seeing you as someone who understands her. If there was never a chance for the two of you, there would be something to count on after asking this and following up with questions like “what’s your worst day ever and how did you cope?”

14.  Apart from your known names, what other name would you like to be called?

It goes beyond being a fun question that sustains a conversation if she gives any name other than her known names or nickname, and doesn’t mind you referring to her with the new name thereafter. It would create a form of exclusivity between you and her, something only the two of you share.

15. What would be the perfect way for someone to ask you out?

This is one of the bold questions to ask your crush. Nothing hints at your intention more than that; if she is a straightforward person, she might create the chance for you to express your feeling by asking why you asked the question.

If romance is a big deal for her and she had thought of being asked out recently, she should give a detailed description that only goes to show she’s expecting someone to ask her out. That person might just be you.

Questions To Ask Your Crush If You’re a Woman Secretly Admiring a Man

Am I Socially Inept?
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It is pretty difficult for a girl crushing on a guy to express how she feels without coming across as desperate. And it takes a mature and serious-minded man to appreciate being crushed on by a lady. As such, women have been advised over the years to not be upfront with men they like; they have been encouraged to hint at their intent and let the men pick it up from there.

It is imperative to point out that there is nothing wrong with taking the lead and asking a guy out if you feel up for it. However, if you want to play it safe, there are several questions to ask a guy you like that would help you find out if he is open to dating you, and as well, reveal to him that you are caught up with feelings for him.

Again, you should start with random questions that are Intriguing and gradually proceed to ones that are personal and intimate.

16. Can you tell me about the most embarrassing day of your life?

Like other intriguing questions to ask your crush that has been discussed thus far, this question is a great conversation starter. More than facilitating a meaningful conversation, it’s a path that leads to being a part of one of the most memorable days of his life. The bond between you and him is bound to have some level of substance thereafter.

17. What do you think is the ultimate secret to happiness and living a fulfilling life?

Through this, you can learn what is important to him and why they are important. In no small manner, an insight into his priorities in life would help you decide if he’s someone to commit to, especially if you still questioning your feelings.

18. Has failure shaped your life in any way?

The failures in life are as important as the successes we attain. So, this question would make you come across as a thoughtful person; who wouldn’t want that attribute in a romantic partner?

19. What are you most focused on at the moment?

Dreams and goals are what define a serious-minded man, and indeed any human that’s determined to live a life of purpose. Given that, you can count this among the powerful questions to ask your crush. It’s a way to make him realize that you are really interested in being a part of his aspirations, nothing is sexier than that.

20. If you have the power to change one thing about the world right now, what would you change?

People are frustrated about so many things in the world, so this question is very handy if you want to engage anyone in a serious conversation. With it, you can practically get to talk about anything and everything you’d like to discuss with him. Nonetheless, be certain you are versed and aware of current events as it would be unfortunate for him to get talking and you can’t keep up with the conversation because you don’t have anything to contribute on the subject.

Flirty Questions To Ask A Man You Like

Things to do when bored
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As much as women are wary of expressing their feelings to a guy who might take them for granted, men are also skeptical of going all out to express their feelings as they fear rejection. If you sense that a man is into you but it is taking forever for them to do the needful, the following flirty questions can go a long way in encouraging them to let the cat out of the bag.

21. What would make you go crazy about a lady?

With suggestive body motions, this becomes a daring way to tell the man you have been admiring that you are attracted to him. It is hard to imagine he wouldn’t capitalize on this to ask you out if he is enthused about you as much as you like him.

22. What qualities must the mother of your kids have?

Depending on his answer, you should know if he is open to settling for family life in the nearest future. For someone that’s looking forward to a relationship that would lean toward building a family together with a prospective partner, this is one of the most important questions to ask your crush. There is no point in pursuing a relationship with someone who isn’t on the same page as you.

23. How did you realize you like me?

Among other flirty questions to ask your crush, this is a bold way of getting him to own up to what and how he feels about you. It should be asked playfully and dismissively. If he strives to discuss it, then there is a great chance he is into you.

24. What did you think of me the first time we met?

A detailed and heartwarming answer suggests he has been caught up with feelings for you. And a shallow one implies you are just another person he knows, especially if you have known each other for a while.

25. If you have the power to choose what I’m wearing right now, what would it be?

This is probably more of a seduction than a question but it is a good one to ask. It can make him more comfortable and free with you. Also, his response can provide insight into how he’s attracted to you.

Questions To Ask Your Crush If Your Are Gay and He’s Straight

Heterosexual relationships can be difficult but for obvious reasons, it is not as difficult as going through same-sex romantic feelings, especially for a gay man crushing on a straight fellow. Even though it seems impossible for a gay to seduce a straight man, some studies have found that straight men go gay more often than people realize. So, it is possible to seduce a straight man but takes a lot of work, commitment, and patient according to this piece.

26. What is the most relevant thing in your life right now

The straight man you are crushing on has to be very comfortable around you, it is a vital process in seducing him and questions like this can help you work your way into anyone’s heart.

27. Have you ever experienced unreciprocated love?

If you suspect the straight guy is secretly gay or curious about homosexual relationships, you can ask this question and allow the conversation to flow naturally, if he is unwilling to open up, don’t push it as you might end up having him distance himself from you.

28. What is your biggest secret?

Generally, this is one of the fun questions to ask your crush. For someone crushing on a straight man, you may never know what you would learn if you didn’t ask this. While the answer might be far from what you hope to ultimately achieve, the question can help form a stronger bond between you and him.

29. What would you have your girlfriend do to get you off?

When you are convinced he is open and free with you, you can ask this and learn about what he likes. You will find it useful when the time is right to make a move. Yes, you will eventually have to take the lead.

30. What do you do in your sexual life?

Like the preceding question, asking a straight man you have been crushing on this question can expose his sexual fluidity; of course, what you learn can be useful in your scheme of seducing him.

Final Words

As often said, you miss 100 percent of the shots you don’t take. So if you find yourself attracted to someone, it’s best to do something about it. From the experiences people have shared, it is better to be rejected than spend a great deal of the rest of your life wondering what could have been. Build up your courage and go for it!


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