Starting a conversation with someone can feel so much harder than it should.
You want to connect, but you don’t always know what to say, then it seems like the moment is over.
That’s where the right conversation starters can help.
These simple, natural and open-ended conversation starters are for when you want to reach out but aren’t sure what to say.
You can use them in person, or use the text message versions that don’t sound as stiff or scripted.
I’ve included both versions in the interest of being thorough. The point is not to memorize anything, it’s to make them your own.
Remember, the goal (as always) is to create a deeper connection. If he wants to talk about something else, let it go there.
Here you go:
Fun conversation starters
These fun conversation starters are light and easy.
They’re the kind of questions that get things rolling but keep the mood between you relaxed.
What’s something random that always makes you laugh?
Text version: I just thought of something. What’s the most random thing that cracks you up every time?
If you could redo one day just for fun, which day would you pick?
Text version: If you could relive one day just for fun, which one would it be?
What’s a movie you can basically quote by heart?
Text version: What movie have you seen so many times you can basically quote it?
Do you like surprises, or do you prefer knowing what’s coming?
Text version: Are you a surprises person or a ‘tell me what’s happening’ person?
What’s a hobby or interest you’ve secretly always wanted to try?
Text version: Is there something you’ve always wanted to try but never have?
What’s the most fun trip you’ve ever taken?
Text version: Out of all your trips, which one was the most fun?
Have you ever had a moment where you thought, “This feels like a movie”?
Text version: Ever had a moment where you thought, wow this feels like a movie scene?
What’s a memory that still makes you laugh whenever you think about it?
Text version: What’s a memory that makes you laugh every time you think about it?
What’s one tradition you’d never want to give up?
Text version: What’s a tradition you’d never want to let go of?
What’s the last thing you did for fun that surprised you?
Text version: What’s the last fun thing you did that actually surprised you?
What’s a little skill you have that most people don’t know about?
Text version: What’s a random skill you have that most people don’t know?
What’s the most interesting place you’ve ever visited?
Text version: What’s the most interesting place you’ve been to?
What’s one thing you’ve done that scared you but you’re glad you did it?
Text version: What’s something that scared you at first but you’re glad you went through with it?
Do you think you’re more of an introvert, extrovert, or somewhere in the middle?
Text version: Do you think you’re more introvert, extrovert, or in between?
If you could eat only one type of cuisine for the rest of your life, what would it be?
Text version: If you had to eat just one type of food forever, what would it be?
What’s a funny or weird superstition you secretly kind of believe?
Text version: Do you have any funny or weird superstition you secretly believe in?
Personal conversation starters
Asking about favorites is a low-pressure way to get to know someone.
These make it easy to find out what he enjoys and what he’s actually like.
If you had to pick one song to play on repeat all week, what would it be?
Text version: If you had to pick ONE song to put on repeat all week, what’s your choice?
What’s your favorite way to spend a Sunday morning?
Text version: Serious question—what’s your perfect Sunday morning vibe?
What’s the strangest food you’ve actually enjoyed?
Text version: Be honest—what’s the weirdest food you’ve ever tried and liked?
What’s your comfort meal?
Text version: What’s your go-to comfort food when you just want something cozy?
Do you have a favorite memory that instantly makes you smile?
Text version: What’s one memory you can think of right now that always makes you smile?
Do you like planning vacations or just showing up and winging it?
Text version: When it comes to trips, are you a planner or a wing-it type?
What’s your favorite season and why?
Text version: Random but important: favorite season and why?
If you had to pick a theme song for your life right now, what would it be?
Text version: What’s something you’ve always wanted to learn but haven’t had the chance to yet?
If you could only keep three apps on your phone, which would you choose?
Text version: If you could only keep 3 apps on your phone, which ones make the cut?
What’s a book, podcast, or show you’ve recommended to someone lately?
Text version: What’s a book, podcast, or show you’ve told someone to check out recently?
MORE: 53 Flirty Questions to Ask When You’re Sick of Small Talk
Storytelling conversation starters
These storytelling conversation starters are nice because they only require him to tell the truth about himself, not think of something new to impress you.
What’s a little detail that can always turn your day around?
Text version: What’s one tiny thing that can totally flip your mood in a good way?
Do you remember the first concert you ever went to?
Text version: Okay, throwback question: what was your first concert?
What’s a little everyday thing you secretly enjoy more than most people?
Text version: What’s one tiny everyday thing you secretly enjoy more than most people?
What’s the best part of your day, most days?
Text version: What’s usually the best part of your day?
If you had a whole free day with no responsibilities, what would you do?
Text version: If you had an entire free day with nothing on your plate, how would you spend it?
Do you like hearing stories about people’s childhoods?
Text version: Random question—do you like hearing childhood stories?
Deep, imaginative conversation starters
Sometimes the most interesting talks come from “what if?” questions.
These let you see how he thinks without it feeling heavy or filled with pressure.
If you could swap lives with anyone for a week, who would it be?
Text version: If you could switch lives with anyone for a week, who’s your pick?
If you could wake up fluent in another language, which would it be?
Text version: If you could wake up speaking another language tomorrow, which one would you pick?
If you could instantly be an expert at anything, what would you choose?
Text version: If you could magically be an expert at one thing, what would it be?
If you could time travel to any era, just for a week, where would you go?
Text version: If you could time travel for a week, what era would you pick?
If you could design your perfect night out, what would it look like?
Text version: If you could plan your perfect night out, what would it include?
MORE: 101 Thought-Provoking Questions To Get To Know Someone
Thoughtful conversation starters
When you want to go past surface-level, these deep and thoughtful conversation starters open up space for more honest answers.
What’s the best advice someone’s ever given you?
Text version: What’s the best piece of advice you’ve ever gotten?
Do you believe in luck, or do you think people make their own?
Text version: Do you believe in luck, or do you think people create it themselves?
What do you think makes someone feel unforgettable?
Text version: In your opinion, what makes someone unforgettable?
What’s a small risk you took that really paid off?
Text version: What’s a small risk you took that ended up being worth it?
What’s one habit you’ve picked up recently that makes your life better?
Text version: What’s one new habit that’s actually made life better for you lately?
What’s the best compliment you’ve ever gotten?
Text version: What’s the best compliment someone’s ever given you?
Each of these conversation starters helps you go beyond small talk so you can learn more about him and create a deeper connection.
A good conversation doesn’t have to be complicated.
You can use these conversation starters to get to know him better, when things get boring, or whatever works best for you.
MORE: 44 Questions to Ask Your Crush or Anyone You Can’t Stop Thinking About
