50 Flirty Conversation Starters to Make Your Crush Smile
Flirting doesn’t have to be complicated — sometimes all it takes is the right question to make your crush laugh, blush, or open up. Whether you’re chatting in person, over text, or on a date, these 50 flirty conversation starters will help you break the ice and build a connection.
The trick is to keep things playful, respectful, and genuine. Use these questions as inspiration, and let the conversation flow naturally.
👉 If you're looking for more ways to keep the dialogue flowing, check out these Best Conversation Starters for Couples Who Want More Fun.
Playful Starters
Perfect for breaking the ice and showing your fun side.
“What’s the funniest thing that’s happened to you this week?”
“If we played Truth or Dare right now, what would you pick?”
“What’s your go-to dance move when nobody’s watching?”
“If we had a karaoke battle, which song would you choose?”
“What’s the silliest nickname someone’s ever given you?”
Compliment-Based Starters
Everyone loves a genuine compliment. These questions add a flirty twist.
“Do you know how good you look when you smile?”
“What’s the secret behind your confidence?”
“If I had to describe you in three words, can I use the word ‘cute’ twice?”
“Do you get told often that your eyes are distracting?”
“Want to hear my favorite thing about you so far?”
Romantic Hypotheticals
Spark their imagination and keep things exciting.
“If we could sneak away right now, where would you take me?”
“What’s your idea of a perfect date?”
“If we could teleport anywhere for dinner, where would we go?”
“Would you rather watch the sunrise or the sunset with me?”
“What’s your dream vacation — and can I come with you?”
Flirty Challenges
Turn your talk into a mini-game.
“I bet you can’t make me laugh in under 10 seconds.”
“Want to play ‘Would You Rather’ — flirty edition?”
“Guess what I’m thinking about right now…”
“Truth or Dare: Tell me your biggest crush moment.”
“If I win rock-paper-scissors, you owe me a secret.”
👉 Turning your chat into a game is a great way to connect. For more inspiration, explore these 15 Playful & Fun Couple Challenges to Bring More Laughter into Your Relationship.
Sweet & Subtle Flirtation
Lighthearted but still suggestive.
“Do you always smile this much, or is it just because of me?”
“What’s the best compliment you’ve ever gotten — and should I top it?”
“What’s your favorite thing someone has done to make you feel special?”
“If we were characters in a movie, what genre would it be?”
“What song would you dedicate to me?”
Spicy Conversation Starters
For when the chemistry is strong and you’re ready to turn up the heat.
“What’s one thing that instantly turns you on?”
“Have you ever had a dream about someone you like?”
“What’s your most adventurous idea for a date night?”
“Would you rather cuddle all night or kiss all night?”
“If I dared you to kiss me right now, would you?”
Flirty Over Text
Perfect for long-distance flirting or late-night chats.
“Guess what I’m wearing right now…”
“What’s the first thing you’d say if I showed up at your door?”
“Should I send you a smile selfie or keep you waiting?”
“What emoji reminds you of me the most?”
“Want me to give you a bedtime thought to dream about?”
👉 For more ideas tailored specifically for your phone, here are 25 Flirty Text Conversation Starters for Couples.
Deep but Flirty Questions
Mixing emotional connection with flirtation.
“What’s the most romantic thing you’ve ever done?”
“Do you believe in love at first sight — or should I walk by again?”
“What’s one small thing that makes you feel really cared for?”
“What’s your favorite memory with someone special?”
“Do you think opposites attract, or do we just match too well?”
Funny & Teasing Starters
Keep the vibe light and charming.
“So, are you always this good at making people laugh, or am I special?”
“What’s the most embarrassing thing you’d admit to me?”
“Do you always flirt this much, or am I lucky?”
“If you could steal one thing from me, what would it be?”
“Do you think we’d survive as teammates in a game show?”
Future-Flirty Starters
Hints at spending more time together.
“What’s one place we should go together this month?”
“What’s your ideal lazy Sunday with me?”
“Would you try a cooking challenge with me?”
“What’s one thing you’d add to our bucket list?”
“If we were planning a weekend getaway, where would we go first?”
👉 If those questions about a getaway have you dreaming, get some real-world inspiration from these Hidden Romantic Getaways: 8 Lesser-Known Destinations for Couples.
How to Use These Questions
Pick the right vibe: funny, sweet, or spicy.
Don’t ask them all at once — let the conversation flow.
Match your crush’s energy and comfort level.
Turn the Q&A into a playful game using the BedPlay app, which has ready-to-use flirty questions and dares.