To meet the right person, you’ll probably have to do a fairly large amount of small talk.
Also, (especially if you’re me) constant boring small talk is the fast track to crushing boredom.
Back when I was still dating, I used to get so bored with this process that I would binge-date in several month stints before quitting and taking a break. Then the cycle would start all over again.
I don’t want that for you or any of my coaching clients who want to meet someone.
And, you don’t want to lose your shot with good potential matches because keeping a conversation going long enough to see if you’re a good fit for each other got tedious.
“Ask a good question” is about the best piece of dating advice I can give you.
That’s what I want to help with today.
Asking good questions helps you seem engaged, open, happy and interesting to talk with. The right question is also a great cover for any nervous energy you happen to be feeling.
On this list, you’ll find flirty questions ranging from casual to more spicy, for every setting— whether you’re sitting across the table from each other or trying to cook up something worthwhile to say over text.
Also, like anything share with you, use your best judgement about which questions are right for you to ask. This list is meant to build on itself with the more provocative questions toward the end.
As a general guideline, the more open-ended the question, the easier it will be for you to create a conversation around it. These flirty questions are meant to be light and fun.
You can find my list of deeper, more thought-provoking questions here.
Remember, you’re just trying to get to know each other, not guarantee they fall in love with you in the first 10 minutes of the date.
Here you go:
Flirty Questions to Help You Break the Ice
- What’s the most fun thing you’ve done this month?
- If you could drop everything and go somewhere for the weekend, where would it be?
- What kind of music instantly puts you in a good mood?
- Which movie could you watch over and over and never get tired of?
- What’s your signature dish in the kitchen?
- What’s your favorite dessert when you want to celebrate something?
- If you could relive one amazing day from your past, which would it be?
- What’s your favorite way to spend a Friday night?
Build a Connection with these Flirty Questions to Ask
- Do you think you’re more spontaneous or more of a planner?
- What’s your favorite way to celebrate a win in life?
- Which season do you think is the most romantic?
- What’s your favorite lazy-day activity?
- Which holiday would you celebrate all year if you could?
- What’s something that always feels like a treat?
- What’s your favorite way to unwind after a long week?
MORE: 101 Thought-Provoking Questions To Get To Know Someone
Flirty Questions To Create Interest
- What’s one little thing that always gets your attention?
- If you had to pick, would you rather have breakfast in bed or a sunset picnic?
- Which do you think is more important to you—chemistry or timing?
- If you could only choose one: passionate kiss or long conversation under the stars?
- Do you think you’d win in a game of truth or dare?
- When was the last time someone made you blush?
- What’s one thing that always makes you smile without fail?
MORE: 44 Questions to Ask Your Crush or Anyone You Can’t Stop Thinking About
Teasing and Fun Flirty Questions to Ask
- If you had to describe your flirting style in one word, what would it be?
- Do you believe in love at first sight, or should it take more than one date?
- Which do you enjoy more: a slow dance or a fast one?
- If someone wanted to sweep you off your feet, what’s the best way they could do it?
- What’s one thing you can never say no to?
- Do you think you’re more of a heartbreaker or heart-stealer?
- What’s your favorite compliment to receive?
Imaginative “What If?” Flirty Questions to Ask
- If you could have dinner with anyone (dead or alive), who would it be?
- If you were given plane tickets to anywhere, where’s the first place you’d want to land?
- If you could instantly master one hobby, what would it be?
- If you could only eat one dessert forever, which would you choose?
- If you could time travel to any year, where would you go first?
- If you won the lottery tomorrow, what’s the first fun thing you’d buy?
- If your life was a movie, what would the title be?
- If you had to plan a date with just $20, what would we do?
Flirty Questions To Build Chemistry
- What’s your go-to song to dance to when no one’s watching?
- What’s one adventure you’ve always wanted to go on?
- What’s your idea of a perfect morning?
- What’s the most memorable kiss you’ve ever had—and why?
- If we were sharing a bottle of wine right now, where would the night go next?
- Have you ever had a date you didn’t want to end?
- If you could steal someone away for a weekend, what would you plan?
- What’s the most daring thing you’ve ever done in a relationship?
- If we danced close, would you whisper something in my ear—or keep it to yourself?
- Have you ever had a moment with someone where the air felt electric?
- If you had to choose between slow and tempting or fast and intense, which would you pick?
- What’s the best kind of trouble two people can get into together?
- If we were the only ones in the room, how would you keep my attention?
MORE: 200 Love Affirmations To Manifest Love (Plus How To Use Affirmations Effectively)
There you have it, flirty questions to ask that will keep the conversation flowing.
Remember, good conversation is rarely about saying the perfect thing, it’s about presence, connection and effort.
Having a few flirty questions like these in your back pocket can make the whole process a lot more fun.
Sometimes all it takes is one unexpected question to deeply connect with someone.
MORE: 125 Butter-Smooth Cute Texts For Him (Savage, Good, Flirty)
