Questions To Ask Your Crush – Complete Guide


Getting to know someone is hard! It can be nerve-wracking to sit across from a gorgeous woman or handsome man and try to figure out what kind of questions to ask. You don’t want to say the wrong thing, but you want to get to know them better.

So what do you do? Ask the first thing that pops into your mind? That could work, but it could lead to some awkward small talk.

Why not be prepared? We’ve come up with a list of questions you can ask your crush in case you find yourself in a conversation lull. These will help you get to know them better, encourage them to open up about themselves, and help you find commonalities that can bring you together. In the end, connecting on a deeper level is the key to any successful relationship!


The Right Way to Ask Questions

When you ask a question, you need to actually listen to the answer they give. Don’t be thinking about your next question or how you can turn what they said into another question to keep the conversation going.

Instead, pay attention to their words, their facial expressions, and their body language. Feel their answer and use those feelings to continue the conversation.


Example of BAD question-asking:

Him: Do you enjoy science fiction movies?

Her: Not so much. I prefer romantic comedies.

Him: Even the funny science fiction movies with romance in them?


The guy in this scenario asked a question, then followed it up with a question that continued with his original line of thinking instead of flowing to a potential new topic that would prove far more interesting to her.


Example of GOOD question-asking:

Him: Do you enjoy science fiction movies?

Her: Not so much. I prefer romantic comedies.

Him: What is your favorite rom-com?


Yes, this is an incredibly basic (small talk) topic of conversation, but it serves to illustrate the point.

When you ask a question, don’t follow it up with another question that continues what you were thinking. Listen to the answer they give, feel it, then ask something that goes off of their train of thought. You’ll find your conversation goes to many more interesting places this way!


Start Small, Get Big

Don’t make the mistake of asking the big, heavy questions right off the bat. Like «How old were you when your parents divorced?» can lead to unpleasant memories, which is the last thing you want on a first date or a quick chat with your crush.

These questions do have a place in your conversation—they’re the ones that really help you get to know someone on a deeper level—but you can’t drop them too early.

Start off with light, smaller and funnier questions (even if they feel like small talk), then delve into the deeper topics over time.


10 Questions to Get You Started

Try these simple questions to help you spark up a conversation and engage the other person long enough to get them interested in you:

  1. What do you do? How do you like your job? — A lot of people are defined by their profession, so asking them about it will get them talking about the thing that interest them. Alternately, you may find they dislike/hate their job, and you can get to know them when you ask about
  2. What is your dream travel/holiday/living destination? – Everyone dreams about traveling. This can be an interesting way to spark up a conversation about places you’ve visited or want to visit—a great way to find common ground.
  3. What’s your favorite thing to do after work? – A light, fluffy question that will give you some insight into their social life, friends, family, hobbies, and interests.
  4. What would be your craziest date idea? – This steers the conversation toward dating, but in a fun way. Easy to back off if he/she doesn’t seem interested, or to press if he/she does.
  5. What is the craziest/silliest/most embarrassing thing you’ve ever done? – We all have stories that we want to share, and this opens the door for you to talk about their past. This can spark a much deeper conversation!
  6. If you could do anything right now, without thinking, what would it be? – Another fluff question, but it can give you a better understanding of their hopes, dreams, passions, and interests.
  7. What makes you happy? – This can be a question that leads to more in-depth conversations, or it can help them open up about their passions, desires, hobbies, and pursuits. Either way, it’s a great question to lob out there!
  8. What is the best gift you’ve ever received? – This is another fun way to bring up their past, including family, friends, and (unfortunately) exes.
  9. What is your favorite book/movie/TV show? – It’s a light question that will lead to a lot of small talk, but a great way to establish common ground. It can also tell you what kind of person they are—their choice in entertainment says a lot about them.
  10. What are three things you look for in a date/crush/partner? – This helps you turn the conversation toward dating and relationships, but it’s still casual enough that it’s easy to salvage the conversation if they don’t show interest in you.

These simple questions are a way to get you started, and it’s up to you to take the answers they give and make them work for you!


10 Questions to Take Your Conversation Deeper

Once you’ve had some small talk, it’s important to try to take the conversation deeper and get to know them better. Here are 10 questions that will help you do just that:

  1. What is your dream profession? Where do you see yourself in five years? – This may seem like a simple question about the future, but it is an excellent way to get people to open up about what they expect from life. Some people are sensitive about their future plans, so they may hesitate to share. If they do, it can help you learn a lot about them and who they want to be.
  2. Has anything happened that changed you? – This is a chance for them to open up about past traumas, successes, and anything else that caused physical or emotional changes. This can be a hard-hitting question that leads to much deeper conversation.
  3. What is something that makes you feel nervous/afraid? – Everyone has their deep-seated fears and anxieties. Talking about them may not feel sexy or flirty, but it helps you get to the root of who they are far faster.
  4. What is your definition of happiness? – We all have our own opinion on what it means to be happy—understanding your crush’s idea of it will help you know what they’re looking for out of life or a relationship.
  5. What are your goals in life? – This gives them another chance to talk about what they want to accomplish with themselves, and can help you get to know them a lot better. Who knows, it may just turn out your goals are aligned!
  6. What was it like the first time you fell in love? – Bringing love into the conversation can help to lead things toward romance, relationships, sex, and emotional connections. It can be flirty, but it’s also a great way to get to know their romantic history.
  7. How would you describe yourself in one sentence/paragraph? – Everyone has an idea of who they are, and their perspective may be different from what you see. It’s an innocuous question that can lead to much deeper topics.
  8. What do you like in a partner more: intelligence or looks? – This one gets things back on topic of relationships and potential love interests. If he/she mentions things that you clearly have, it may be a sign they’re interested in you.
  9. Do you have any tattoos or piercings? – This is a very flirty question, because it brings up conversations about personal, private things (pierced or tattooed body parts). On the other hand, if they say they don’t have either, it can spark a conversation on why not.
  10. What is your happiest memory as a child? — Talking about childhood and the past is a good way to get to know someone, and this question can open up a conversation on their parents, relatives, siblings, friends, and other people that were important in their lives.


The right questions can help you to get to know your crush on a much deeper, more emotional level. In the end, that’s what leads to a successful, well-grounded relationship!