25 Questions to Ask Your Crush
Navigating the early stages of attraction can be thrilling yet intimidating. When you’re drawn to someone, it’s natural to want to know more about them—but how do you ask the right questions without seeming too forward or putting too much pressure on the conversation?
As a dating coach, I’ve seen it all: the awkward silences, the overthinking, and the missed opportunities. But asking your crush thoughtful, engaging questions can spark deeper conversations and build a stronger connection.
Here’s a list of 25 questions to ask your crush—questions that will help you learn more about them, while also allowing you to show genuine interest without coming off as intrusive.
What I have done here is taken a look at some of the cliche type of questions that you could ask and alongside of them gave an example of what would add a bit more flavour and personality whilst giving you the same response.
Remember it’s always going to be about breaking patterns and the same to be true with our conversation.
If you are asking questions that seem generic then she may switch off into the dreaded ‘yawn zone’.
- What’s your perfect way to spend a weekend? / If I had to give you a week off work how would you spend it ?
This question helps you gauge their hobbies, interests, and whether you share any common ground. Plus, it opens the door to potential date ideas.
- What’s one thing you’ve always wanted to try but never have? / When was the last time you allowed yourself to experience something for the first time ?
This shows curiosity about their dreams and aspirations. It also gives you insight into what they value or what excites them.
- Do you believe in love at first sight? / Have you ever been completely taken back after meeting someone for the first time ?
This question opens up a conversation about their perspective on love, which can reveal how they approach relationships.
- What’s the most memorable trip you’ve ever been on? / If you had to cast your mind back and be given the opportunity to live that one day out for the rest of your life, what would it be ?
Travel is a topic many people love discussing, and it can lead to sharing funny or meaningful stories, allowing you to bond over experiences.
- What’s your go-to comfort food? / What’s the sexiest thing in your fridge ?
Food is a universal topic, and this question not only allows for a light conversation, but it also helps you understand what brings them joy in their everyday life.
- If you could live anywhere in the world, where would it be?
This can reveal their sense of adventure, lifestyle preferences, or their desire for a specific culture or environment.
- What’s your favourite book or movie and why? / What are you currently reading ? / What’s a movie that you’ve seen that you feel is the most relatable to you ?
People’s taste in media often tells you about their personality. This question can also lead to deeper conversations about shared interests in films or books.
- What’s something that always makes you laugh? / What’s made you chuckle recently ?
Humour is a great way to connect. Whether it’s a comedian, a movie, or something quirky about their own life, humour tells you a lot about a person.
- Are you a morning person or a night owl? / What time do you normally have to wake up? / When’s bed time for you ?
This seemingly simple question helps you understand their lifestyle and daily rhythms. Plus, it’s an easy topic to joke around with.
- What’s your biggest pet peeve? / What’s your biggest Icke ?
Knowing someone’s pet peeves helps you understand what frustrates them, and sharing your own can create a sense of camaraderie.
- How do you usually spend your free time? / What’s your hobby ?
This question can help you learn what makes them feel relaxed or happy, whether it’s a hobby, sport, or social activity.
- What’s something you’re really passionate about? / What’s something that really get’s your juices going ?
When someone talks about their passions, it can lead to a really engaging and exciting conversation. Plus, it shows what drives them in life.
- What’s the best advice you’ve ever received?
This question can open up a conversation about life values, personal growth, and the experiences that have shaped their mindset.
- What’s your love language?
Understanding someone’s love language can be incredibly insightful, especially if you’re exploring a potential relationship with them. This helps you understand how they express affection.
- What’s one of the most important lessons you’ve learned so far? / What have you learnt about yourself recently ?
This question taps into their life experiences and can lead to a meaningful conversation about growth and personal development.
- What’s something that really motivates you?
What drives a person tells you a lot about their goals, ambitions, and overall personality. Are they motivated by career, family, or personal growth?
- If you could meet any historical figure, who would it be? / If you had to host a dinner party and anyone could be there from past and present who would you put around the table ?
This question can lead to some fun historical discussions, and you can learn about their interests and values based on their choice.
- What kind of music are you into? / What’s on your playlist right now ?
Music is a great bonding topic. Whether you share similar tastes or find out about something new, music can be a way to connect emotionally.
- What’s the craziest thing you’ve done on a dare? / `What’s the wildest experience you’ve allowed yourself to explore ?
Everyone loves a good story, and this one might just reveal some wild or funny moments from their past.
- Do you believe in fate or do you think we create our own destiny? / Where are you at in terms of your spirituality ?
This philosophical question can lead to a deeper discussion about beliefs, values, and life choices.
- What’s one skill you’ve always wanted to learn? / What’s something new you want to explore ?
This question opens up a discussion about curiosity and personal development. It can also reveal opportunities for shared experiences, like learning something together.
- What’s your idea of a perfect date? / What’s the shittiest date you’ve ever been on ?
If you’re both into each other, this question helps you gauge what kind of romantic experiences they enjoy, which could lead to an ideal date idea in the future.
- What’s one thing you can’t live without? / What’s one thing you need in your life everyday ?
This reveals what’s truly important to them, whether it’s something material (like their phone) or something more abstract (like family or freedom).
- Do you have any hidden talents? / What’s your party trick ?
This question opens the door to learning something unexpected and fun about them. It can also lighten the mood and create a playful vibe.
- If you won the lottery tomorrow, what would be the first thing you’d do? / If you had all the money in the world how would you spend it ?
This question sparks a conversation about their dreams, values, and how they might spend their newfound wealth. It’s a fun way to learn about their priorities in life.
In Summary
Asking your crush the right questions isn’t just about gathering information—it’s about creating meaningful conversations that allow you to bond on a deeper level. The key is to keep things light, fun, and respectful. Don’t feel like you need to rush through all 25 questions in one sitting. Let the conversation flow naturally, and choose questions that feel right for the moment.
Ultimately, the goal is to get to know your crush better and find common ground. By asking open-ended, thoughtful questions, you can create an atmosphere of mutual curiosity, understanding, and excitement. So go ahead, ask these questions, and enjoy the journey of getting to know someone special!
Get in touch with dating coach Johnny Cassell today, and check out some his renowned courses such as remote coaching, group workshops and the popular 7 day programme!