♡ A LITTLE MOMENT FOR TWO · ALWAYS FREE
Flirty Questions to Ask a Guy
Add a little playfulness to a conversation while following the other person's comfort. Start sweet and let the mood grow naturally.
Take turns answering; ask a follow-up when something catches your curiosity.
How to play
- Read one prompt aloud, or share this page alongside your usual call.
- Take turns answering. Ask one follow-up before moving on.
- Skip anything that does not fit the mood. A good conversation can be your last round.
What would your excuse be for making a coffee date last a little longer?
Free to play. No account needed.
KEEP A FAVORITE FOR ANOTHER EVENING
All 60 questions
Browse at your own pace, or explore the cards above. Pick what fits the two of you today.
Questions 1–20
What would your excuse be for making a coffee date last a little longer?
Do you believe in love at first sight, or should I walk by again?
Which song would you choose for the moment I walk into a room?
If you could take me anywhere right now, where?
What tiny detail would you hope I noticed if you planned a date?
What's something about me that caught you off guard?
If you sent me a one-line invitation, how would you make it hard to ignore?
What's your love language?
What would you put in a picnic basket chosen to make me smile?
What's the boldest move you've ever made on someone?
Which harmless challenge would you use as a reason for a second date?
What's your biggest green flag?
What would you say if I asked whether you had been looking forward to seeing me?
If I dared you to do something right now, would you do it?
Which café seat would you save for me?
What's your honest opinion of my last text?
What would be your signature move as an extremely polite romantic-comedy lead?
How long did you wait before replying to my first message?
Which compliment would you give me if you had to avoid the obvious ones?
What's a message you typed out and deleted before sending?
Questions 21–40
What would you name a playlist intended only for our evening?
What's something small I do that you find attractive?
How would you ask me to join you for one more walk around the block?
Do you think you're a good kisser, or should I be the judge?
Which detail of a message makes you think someone might be flirting?
What's your type, and how close am I?
What would you do if I guessed your favorite date idea correctly?
If I showed up at your door right now, what would we do?
Which fictional setting would give us the best excuse to keep talking?
How would you react if I kissed you right now?
What would be a sweet way to tell me you were a little nervous?
If we got stuck in an elevator for an hour, how would we pass the time?
Which small gesture would you like to see returned if you offered it?
What would you plan if you had 24 hours with me and no budget?
What would you write on a napkin instead of saying out loud?
What song would be playing in the background of our perfect night?
How would you turn an ordinary errand into an invitation for me?
What's your ideal lazy Sunday with someone you like?
Which moment on a date makes you want to lean into the conversation?
What made you decide to talk to me in the first place?
Questions 41–60
What would you tell me about yourself to earn a curious follow-up?
What's something you've wanted to tell me but haven't?
Which nickname for our next outing would make you laugh?
What was the last thing you thought about before falling asleep?
What would be your opening line in a postcard sent from one room away?
If we swapped lives for a day, what's the first thing you'd do?
How would you invite me to choose the music without ending the conversation?
What would the trailer for our story look like?
Which little romantic cliché would you happily try if we both found it fun?
What nickname would you give me if you could get away with it?
What would make you smile if I remembered it next time?
Do you get nervous around me, or is that just me?
How would you suggest we see the same sunset together?
How do you know when you actually like someone?
Which part of a good goodbye would you like to slow down?
What's a look you've caught me giving you?
What would you hope I wrote after saying I had a good time tonight?
What's your idea of a perfect goodnight?
What small plan would you be tempted to make with me before the evening ends?
What's a question you've been hoping I'd ask?
A little permission to take it slowly.
Choose one question when you have time to listen. There is no need to get through the whole collection.