Meeting a new crush is a wild mix of butterflies and brain fog. You’re side-eyeing them in hallways, manifesting miracles, and hatching elaborate schemes with your friends just to break the ice.
Whether you’re using dating apps or going retro with a handwritten note, one thing stays the same: asking the right questions makes all the difference.
But even the right questions come with their own minefield of worries. You’re constantly walking a tightrope wanting to be charming without sounding clingy, curious without being creepy.
That’s why we’ve gathered a list of thoughtful, mood-based questions, so you don’t have to overthink every text or moment. Whether things are just beginning or picking up steam, these can help keep the conversation flowing.
First-Move Questions to Ask Your Crush
Making the first move is never easy. You’re sweating bullets, fumbling your words, and hoping the ground doesn’t swallow you whole. But sometimes, all it takes is the right question to shift everything.
- I have an extra ticket to this new movie, would you like to come?
- Are you on any of the dating apps?
- Would you like to meet for some coffee later on?
- Thinking of you makes me smile. Why do you think that is?
- Are you seeing someone right now?
- What are you doing this weekend? I was hoping to ask you out on a date.
- I have a feeling we’d have so much fun on a date, don’t you think?
- Would you like to get a drink sometime?
- You’ve been on my mind a lot lately. Would you be interested in getting dinner?
- Do I have permission to hold your hand?
- I’ve been loving our conversations lately, have you?
- I think we owe our chemistry one shot, don't you?
- When do you think is the right time to make a first move on someone?
- Have I been too obvious about my feelings for you?
Questions to Ask Your Crush Over Text
In the 21st century, if you’re not a smooth texter, you might as well kiss your crush goodbye. It goes without saying that being prompt with your replies is of utmost importance, as is asking the right questions, since texts lack the aspect of tonality that could possibly jeopardize your chances.
- What’s something you’ve been meaning to tell me but haven’t yet?
- Is there anything you almost texted me but then deleted?
- Do you ever type out a reply to me and then wait before hitting send?
- What’s one thing you wish people asked you more often?
- If I showed up at your door with snacks right now, what would you want me to bring?
- Would it be weird if I said I missed your texts?
- Be honest, have you ever re-read a text from me more than once?
- Have you ever waited to text me just so you don’t seem too eager?
- If I texted you “come outside” in the middle of the night, would you come out?
- Do you ever read one of my texts and smile?
- If you could only send me one emoji to sum up how you feel about me right now, which one would it be?
- If I texted you “I miss you,” would you come over?
- Would you notice or assume I’m busy if I disappeared from your texts for a day?
- When you’re bored, do you ever scroll back through our chats?
Questions to Ask Your Gym Crush
Now, a gym crush is a whole other ballgame. You see each other every day, sneak glances between sets, and never really say a word to each other. It can be daunting to make the first move, but things don’t have to be complicated since you both already have something in common: fitness.
- Can you spot me for a quick set?
- Could you help me film this set? I need to check my form.
- I’ve seen you here all week. Are you training for something?
- How do you make lifting look so good?
- What’s the secret behind your form?
- Are we on the same schedule, or are you secretly following me?
- I was gonna grab a smoothie after this, want to join?
- Can you show me the proper form for this bench press? I’m still learning.
- Do you happen to carry extra liquid chalk?
- Mind if I work in, or are you almost done with this set?
- You always seem so focused. Mind if I join you on this machine?
- What do you usually listen to while you train?
- Is it just me, or do we keep running into each other for a reason?
Good Questions to Ask Your Crush When You Don’t Want to Overthink It
These are foolproof questions you can ask without stressing about timing or vibe. They’re simple, natural, and always a safe bet. They'll keep things light and playful without feeling forced, whether you’re just starting to talk or already in a flirt groove.
- What’s something you’re obsessed with lately?
- What’s something small that instantly improves your day?
- What’s your favorite way to spend a Sunday?
- Do you believe in luck or timing more?
- What’s your go-to movie when you need comfort?
- Do you fall asleep with music, podcasts, or silence?
- If I showed up unannounced, what snack would win me points?
- What’s a moment that made you feel genuinely happy this week?
- What’s a little thing someone could do that would totally win you over?
- What’s your favorite way to reset after a long day?
- When’s the last time you were really proud of yourself?
- What always cheers you up, no matter what?
- If we were on a road trip, who’s picking the playlist?
- What’s something about others that gives you the ick instantly?
Conversational Questions to Ask Your Crush
These “keep it going” prompts invite real answers, not just a yes or no. They’re ideal for turning small talk into a proper vibe, especially when you’re past the icebreaker stage.
- What’s something you could talk about for hours?
- What’s the best conversation you’ve had recently?
- Do you like deep talks or light banter more?
- What’s your favorite way to spend time with someone you like?
- What’s your idea of a perfect late-night walk?
- What’s a topic that instantly brings out your opinions?
- How do you know when someone really likes you?
- What’s something you’ve been wanting to do lately but haven’t?
- When do you feel most like yourself?
- What’s your favorite kind of people to watch?
- How do you usually keep a conversation going when it starts to fade?
- What’s something you never get bored of talking about?
- What’s a topic you secretly love but rarely talk about?
- What’s something you wish people noticed more in a conversation?
- What’s something that instantly makes your day better?
Nostalgic Questions to Ask Your Crush
These aren’t just childhood flashbacks but more like prompts designed to explore defining moments, turning points, and glimpses of who your crush used to be. Whether it’s something they’ve outgrown, held onto, or secretly miss, these questions should help you see their past through a more thoughtful, grown-up lens.
- Which movie or album still feels like a part of you, no matter how much time passes?
- Is there something you once loved but grew out of?
- Can you remember the exact moment you stopped feeling like a kid?
- Do you ever miss a version of yourself that no longer exists?
- Was there one decision that completely changed where your life was headed?
- Is there a place from your past that still feels like home, even if you haven’t been back in years?
- What comfort ritual did you swear by as a kid or teen?
- Is there an old version of you that you’re quietly proud of?
- Can you think of a time you took a leap that actually paid off?
- Looking back, is there something in your past that unexpectedly shaped your identity?
- How did you define freedom when you were a teenager?
- Has someone ever said something to you that still plays in your head?
- Do you see anything from your past completely differently now?
- What’s one spontaneous choice that turned out way better than expected?
- When did you realize you were tougher than you thought?
- Is there a moment you wish you could do over again?
- Can you think of a time from the past that still gives you chills?
- Looking back, what’s something that happened to you that you’re deeply thankful for?
Questions to Ask Your Crush If You’re a Foodie
Food is your love language, and you’re not about to let anyone shame you into thinking pineapple belongs on pizza. You live to eat and need a crush who agrees that frozen cheesecake is a culinary crime.
- What’s your go-to French fry dip?
- Is chili a soup, or does it deserve its own category?
- What would be on the menu if you had to plan the perfect three-course meal?
- Michelin-starred fine dining or a taco truck that slaps?
- Is there a food you absolutely need every day?
- What’s your one snack or meal that always hits the spot?
- What’s your ultimate food pet peeve?
- How do you feel about fruit on pizza?
- Got a go-to gelato place that no one knows about?
- What’s a food trend everyone loves that you just don’t get?
- What’s your all-time favorite food city?
- Is a hot dog secretly a sandwich?
Playful Questions to Learn More About Your Crush
Sometimes, being direct isn't the best move. If you want to uncover your crush’s hidden quirks without putting them on the spot, these clever conversation starters are your go-to.
- Do you think you’re a good kisser?
- Have you ever used whipped cream for a purpose beyond its intended use?
- Have you ever snooped through your partner’s phone?
- What stereotype are you most like?
- What’s the one thing about you that hasn’t changed in the last 10 years?
- What was your shortest relationship?
- What do you think of polyamory?
- What’s one thing you’re surprisingly judgmental about?
- How long do you think it’s acceptable to not respond to someone’s text?
- Have you ever broken someone’s heart?
- What is something you fantasize about often?
- Do you believe in soulmates?
- What keeps you up at night?
- What’s your best pickup line?
Probing Questions to Vet Your Crush Early
Everyone puts their best foot forward at the beginning, but it takes the right questions to move past the surface. These prompts help uncover flaws, values, and the kind of baggage your crush might be carrying without making it feel like an interrogation.
- What is a misconception people have about your personality?
- Hypothetically, if you have one year to live, how would you spend it?
- What was the scariest moment of your life to date?
- How’s your relationship with your mother?
- What do you think is your most toxic trait?
- What is your ex’s version of your breakup?
- Is there a question you hate being asked?
- Have you ever done something you feel guilty about, but haven’t told anyone?
- What’s one thing about your childhood that you’d never want to repeat?
- What’s something embarrassing you did that still makes you cringe?
- Have you ever regretted any of your previous relationships?
- What’s your biggest fear?
Deep Questions to Ask Your Crush
Once the initial spark settles, the next step is a real connection. These deep-cut questions are designed to reveal how your crush handles relationships, views themselves, and defines emotional growth. Perfect for meaningful pillow talk or a serious DTR moment.
- Why did your previous relationship end?
- How do you deal with conflict?
- What are the top three things you seek from a partner?
- Have you ever been in love?
- Do you consider yourself a good person?
- Have you done something in the past that you regret to this day?
- What’s a problematic personality trait that you worked towards changing?
- Do you have a specific attachment style?
- What are three of your biggest relationship deal breakers?
- When was the last time you were in love?
- Have you entirely healed from your previous heartbreak?
- Is there something you’d need from me to feel secure?
- What’s one habit of yours that your ex disapproved of?
- What is your idea of happiness?
Hard Truth Questions to Ask Your Crush
You’ve secured the dynamic, and the banter is bouncing off the walls, but now you feel something different: fear. All this time together has amplified your feelings, and the rate at which your heart beats has gotten you wanting to ask potentially terrifying questions before you take the plunge
- What would your ex say about you?
- Have you ever cheated in the past?
- Is there a life lesson you had to learn the hard way?
- Have you ever betrayed someone you love, and why?
- How do you feel about crying in front of me?
- Do you think anyone or anything is worth dying for?
- What’s one thing about me that you find annoying?
- Do you think your ex gave you trauma?
- What’s something that hurt you recently?
- Have you ever been cheated on?
- What wouldn’t you do for someone you love?
- What’s your process for moving on from someone?
- What’s the most difficult conversation you’ve had with a partner?
- What’s something you’re afraid to tell me?
Questions to Ask Your Crush About Money
A relationship might begin with sparks, but long-term stability often hinges on how you both handle money. These questions are about values, habits, and how each of you sees your future when real-life bills come into play.
- Do you usually stick to a budget or play it by ear month to month?
- Have you ever tried investing in stocks, crypto, or otherwise?
- How do you feel about splitting expenses in a relationship?
- Do you think couples should always keep some finances separate?
- What’s one financial goal you’re currently working toward?
- Have you ever had a financial mistake that cost you a lot?
- Should the person who initiates the first date always cover the bill?
- What’s your take on traditional roles regarding money in relationships?
- Have you ever ended a relationship over money differences?
- Would you feel comfortable supporting your partner temporarily if they lost their job?
- How would you describe your relationship with spending and saving?
- What’s something you’d splurge on guilt-free, no matter the cost?
- How do you usually handle tight budget weeks?
Sweet Questions to Make Your Crush Smile
When the vibe is secure and the feelings mutual, it’s time to bring out the fun. These playful questions are all about being charming, a little corny, and unapologetically sweet.
- What’s something goofy you do when no one’s watching?
- Do you like being called ‘babe’ or ‘baby’?
- What’s my contact name on your phone?
- What silly nickname would you give me?
- What’s one compliment from me that you’d never get tired of hearing?
- What’s something I do that makes you blush?
- Do you like it when someone plays with your hair, or does that annoy you?
- Who’s the first person you think about when you wake up?
- What do you think of me wearing your clothes?
- What’s one thing I do that always makes you smile?
- Would you ever let me princess-carry you?
- Do you have a favorite cheesy compliment?
- What’s my number saved as in your phone?
- Be honest: Am I your favorite person to talk to right now?
Questions to Ask Your Crush to Take Things to The Next Level
You’ve gone past the playful stage and are now wondering where this thing is headed. These questions are designed to gently steer the conversation toward clarity and commitment, without coming on too strong.
- Where do you see us going?
- Do you see me in your future five years from now?
- When do I get to meet your friends?
- Do you ever think about what it’d be like if we lived together?
- Would you want to spend the holidays together?
- Have you told anyone close to you about me?
- Do you want to make things official?
- What’s the group chat’s verdict on me?
- Are we officially a couple now?
- Can I count on you when life gets chaotic?
- Would you want to spend a weekend away together?
- Is it weird that I imagine little things, like keys at your place?
- Would you introduce me to your family?
- Do you feel like this is turning into something real?
Flirty Questions to Ask Your Crush
You’re at a point where your crush likes you, but this far in the development with your crush, that’s simply not enough. You want to be desired, set the mood and want to get them just a tad bit uncomfortable with questions that will rizz them up.
- Would you say yes if I asked you to kiss me right now?
- What’s something totally random that turns you on?
- What’s the first thing you noticed about me?
- Do you like it when someone compliments your lips?
- What’s something about me that you secretly find irresistible?
- What kind of touch makes you melt?
- Where would you want it to end if we were on a date right now?
- Do you like the way I smell?
- Did you wear that perfume for me today?
- What were you thinking about the last time you saw me?
- Do I ever make you feel a little nervous, in a good way?
- What’s something about me you haven’t told me you like… yet?
- What’s one way I could make you blush right now?
- Would you rather I kiss you on the cheek or the lips?
Steamy Questions to Ask Your Crush
Things are getting hot, and you’re ready to take the next step? Risqué questions are tricky, but if approached correctly, you’ll know who you’re getting in bed with in no time.
- Do you enjoy giving pleasure more or receiving it?
- What position in bed are you still keen to try but haven’t?
- Is there a sexual fantasy you’re really keen to try?
- How do you feel about role‑playing in the bedroom?
- Do you like it when your partner takes control of you in bed?
- What’s the most sensitive spot on your body?
- What’s one thing you secretly wish I’d do to you when the lights go out?
- What do you think of socks in bed?
- What’s the most adventurous place you’ve done it?
- Is it wrong of me to wonder what your lips taste like right now?
- What’s on your hot bucket list you want to try with me?
- Where would you want me to kiss you first if we were alone right now?
- Would you be tempted to pull me into the shower with you?
- What if I told you I am not wearing any underwear today?
- Would you take me here, right now?
Intimate Questions to Ask Your Crush
You’ve crossed into a deeper connection and shared a steamy moment. Now comes the pillow talk, but suddenly your mind’s gone blank. These thoughtful questions are just the thing to turn quiet comfort into real emotional closeness.
- What’s one thing you’re not in love with about yourself?
- When can you feel fully yourself with someone?
- What would be a little gesture that would mean the world to you?
- Have you ever caught yourself smiling just thinking about us?
- What’s something I do that makes you feel instantly at ease?
- What’s something you secretly need but often don’t know how to ask for?
- Do you feel close enough to me to share the most intimate bits of your life?
- What’s something about me that caught you off guard in a good way?
- What’s a habit of mine you find weirdly endearing?
- What’s something you’ve always wondered about me but never asked?
- Have you ever felt nervous around me?
- What makes a relationship feel meaningful to you?
- When do you feel most relaxed around me?
- Why do you feel drawn to me?
Weird Questions to Ask Your Crush
They’ve seen your romantic side, they’ve seen you angry, and they’ve seen you horny, but there’s another side to you that’s arguably more intimate than when ya’ll get hot and heavy. It’s the 3 am version of you, brimming with existential questions about aliens, the afterlife, and delusional fantasies that you're ready to share with your crush.
- What animal do you think matches your personality the most?
- If you could swap lives with me for a day, what’s the first thing you’d do?
- Toilet paper: over or under?
- What’s one totally useless skill you’re oddly proud of?
- What would you rename yourself if you could, and why?
- Do you ever lie awake wondering if aliens find us ridiculous?
- If your soul had a color, what would it be and why?
- In a zombie apocalypse, do you think you’d be a hero or a survivor?
- What’s your go-to comfort cringe movie?
- Is there a random smell that instantly brings you back to childhood?
- What’s a conspiracy theory you don’t believe, but still kind of wish were true?
- If you could freeze time at any age, what age would you pick?