100 Questions to Ask Your Crush, IRL or Over Text

Having a crush can feel equal parts exhilarating and terrifying. Your heart races just thinking about them, yet speaking face-to-face makes you tongue-tied.

So how do you move from crush to meaningful connection if conversation doesn’t flow easily? The solution is asking the right questions.

Thoughtful questions for your crush reveal who you both truly are under the nervousness and excitement. They receal your personalities, values, dreams – and compatibility. The answers give essential clues whether this person deserves crush status or something more.

Crafting questions for your crush is an artform.

They should spark lively exchange, not sound like a job interview. You want to balance lighthearted flirtiness with deeper discovery. Most importantly, they open the door for vulnerability and honesty on both sides.

So if you have your sights set on getting to know that cutie better but aren’t sure where to start, this list has you covered.

From fun icebreakers to flirty queries to ones delving into hopes and values, these conversation starters hit all the right notes. They provide the building blocks for potential intimacy and maybe even romance to bloom if the fit feels right.

Now that the introductions are out of the way, let the questioning begin!

Good Questions to Ask Your Crush

If you could learn any new skill instantly, what would you want to learn?
What’s one of your favorite childhood memories?
Where’s the most peaceful place you’ve been? What was special about it?
What music have you been listening to lately?
What’s your favorite childhood memory? What makes it special?
What are a couple things that always make you happy no matter what?
If you could revisit any age or event in your life, what would you want to relive?
What would your perfect day look like?
Who’s someone who has really impacted your life? How so?
What’s something you want to accomplish in the next 5 years?
What do you enjoy learning about most?
What’s your favorite way to spend a day off?
Where is the most interesting place you’ve traveled to? What made it so interesting?
Do you have any goals you’re working towards lately? What motivated you to choose those?
What gets you really excited or passionate?
Are you more of a morning or night person?
What are some of your top interests or hobbies outside of work/school? How did you get into those?
What would your perfect weekend look like?
Who are some of the most inspirational people in your life and why?
What is your most embarrassing moment?

Flirty Questions to Ask Your Crush

If you could take me on a dream date, where would we go? 😍
What do you find most attractive about me so far? 🥰
Have you had any flirty dreams about me lately? 🤫
What your go to karaoke song lately?
Do you have a signature move to make your kisses extra steamy? If yes, demonstrate please! 😘
On a scale of 1 to 10, how good a kisser do you think I probably am? 👄
What is your favorite movie of all time?
Where exactly would you sneak quick kisses with me if we were out together? 😙
Have you peeked at my lips or body when you thought I wasn’t looking? 👀
How would you describe my lips using only emojis? 💋👄🤫
If we slept in the same bed, would you want to cuddle all night or give me space? 🛏
What kind of sleeper are you – wild and restless or calm as a log? 😴
On a scale of 1 to 10, how strong is the chemistry between us so far? 🔥
How would you rate my flirting skills? Any advice to drive you crazier? 🤪
What dating norms would you throw out the window when wooing me? 🤷‍♀️
Have you pictured what I probably look like underneath my clothes? 👗
My best physical attribute is probably my __. Would you agree? 🍑
On a balcony under the stars or snuggled by a cozy fireplace – which sounds more romantic? 🌌🔥
If I was your girlfriend and stole a shirt of yours to wear, how crazy would that drive you? 👕😜
Would you say I’m more of a Marilyn Monroe or Audrey Hepburn classic beauty? 💁‍♀️

Deep Questions To Ask Your Crush

Who has been the biggest inspiration in your life so far?
What’s something you believe really strongly?
What quality do you value most in a friendship?
What’s one of your favorite memories from childhood?
What are you most thankful for in life right now?
What’s something you think everyone should do at least once in their lives?
What’s something that motivates you or that you’re passionate about?
Where do you find peace and clarity when things feel chaotic?
What personal goals are you working towards now?
If you could travel back in time, what advice would you give your younger self?
Where do you see yourself in 10 years?
What’s your biggest fear?
What is one of your top priorities in life right now?
Who has been the most influential person in your life so far?
What inspires you to reach for your dreams?
Do you have any role models? What traits do you admire in them?
What’s something you believe in strongly these days?
Do you think you’ve ever broken someone’s heart?
What is one accomplishment you’re really proud of?
If you had unlimited funds, what charity would you support and why?

Juicy Questions To Ask Your Crush

Who is your biggest celebrity crush and why?
What’s one accidental text you’ve sent that was very embarrassing?
Are you a dog or a cat person?
What’s your biggest regret?
What’s your biggest turn on physically?
What public place would be the most thrilling to get frisky in? 🙃
What was your genuine first impression of me when we met?
Have you ever sexted before? Did you enjoy it?
What’s the sexiest quality I have according to you? 😈
If I touched you in just the right way, where would you melt?
What is your biggest guilty pleasure?
What’s the most daring thing you’ve done in the bedroom?
How many past relationships have you had?
What’s something naughty we should add to a sexual bucket list?
Would you feel comfortable getting adventurous outdoors together?
Have you been into any serious relationship before?
Boxers, briefs or boxer briefs – what do you find hottest?
Slow and steamy or fast and fiery – what’s your preference?
What’s the fastest way to turn you on? 😍
If you could tell your younger self anything, what would it be?

Romantic Questions To Ask Your Crush

What do you think a perfect date looks like?
Do you believe in love at first sight or should I walk by again?
Have you had your first kiss? 😚
What’s your love language?
Would you ever consider going on an exciting spontaneous adventure with me?
What are some things that are important for you in a relationship?
How would your ideal partner make you feel appreciated?
If I gave you a bouquet of flowers, what kind would you want?
Have you had any dreams about me lately? Feel free to describe them!
What do you find sexiest about me so far?
Do you see this blossoming into a deeper connection down the road?
Would you be open to making things official someday if things continue going well between us?
How can I be a better partner to you moving forward?
If you could map out our perfect future together, what would it look like?
Would you ever relocate to another city or country for love?
What song or movie reminds you most of me or makes you think of me?
If I was by your side right now instead of miles away, what would you want to do together?
What food do I need to try that you’re famous for making perfectly?
Do you think stargazing under the full moon would be romantic or cheesy?
Of all the people in your life, why do I stand out to you most?