50 Text Conversation Starters To Go Beyond “Hey”

I get it: You really want to start a conversation with your Tinder match or a crush. 

But you’re not sure what to say. Damn.

You don’t want to sound too keen and obvious by saying something totally random that’s clearly just trying to get their attention. But neither do you want to wait much longer. After all, you want to talk to them!

Here’s the thing: Conversation starters are tough. Get it wrong and they might not reply. And even if they do reply, the starter might inspire a dull conversation that literally goes nowhere

So what do you do?

The key to a good conversation starter is that it’s nothing too heavy, nothing too generic, and that it’s so open-ended that it could encourage a number of different responses.

Oh, and it helps if you can elicit their curiosity so that they wanna see where this is going.

Let's take a look at the 50 best text conversation starters. 

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50 Text Conversation Starters

Are You Up To Much This Weekend?

Do people really like to be asked what they’re up to this weekend?

OF COURSE.

When you ask your crush what they’re up to this weekend, you’re doing two things: You’re taking an interest in their life, but you’re also leaving the door open for the two of you to meet if they’re clearly not too busy.

Describe Yourself In Three Words …

Okay, some people definitely don’t like talking about themselves.

But asking them to describe themselves  in just three words via text is way less heavy than asking them over the phone.

What’s Your Favourite Time Of The Year? 

Everyone has a favorite time of the year. But what’s theirs and why? What does it remind them of? What memories might they have attached to it? 

What’s Your Biggest Dream? 

Having dreams is amazing – sharing dreams with others is even better. Ask this to encourage your crush to truly open up to you about their wildest dreams and hopes. 

Who’s Your Biggest Inspiration?

I love this question because I feel that our role models tell us a lot about ourselves. They show us who and what we aspire to be, and the thing is that everyone has at least one person who inspires them. 

What Can’t You Live Without?

Most people probably answer this question with “computer” or “phone.” But you never know – your crush might surprise you with a surprising answer. 

Or maybe they’ll just say shoes for a girl or football for a guy. Ha. 

What Would Surprise Me The Most About You?

We’re all complex, multi-faceted people who are capable of surprising people. Maybe your crush is a secret chess champion, or maybe they still believe in Santa Claus. Or maybe they used to play in a thrash metal band. 

Or maybe he/she has a weird fetish for serial killers (we hope not). 

What’s Your Biggest Fear? 

Everyone has fears so they’ll totally be lying if they said “I am scared of nothing.” Ask this question to learn what her biggest fears are, and to also share yours. 

Alternatively, you could rephrase it as, “does anything scare you?”

What Could You Tell Me That You’ve Never Told Anyone Else?

If she’s only just getting to know you, the chances are that she won’t tell you anything.

But if the two of you are a little further down the line, she might be open to revealing something that no one else knows, and which brings the two of you closer together.

Have You Changed Much Over The Last Ten Years?

Some people change loads from when they were a teenager to when they’re a proper adult. Asking this question will give you insights into what she was like, what she is like – and how much more comfortable she is now. 

If You Could Change One Thing About You, What Would It Be? 

For some reason, some people don’t mind talking about their flaws one bit. Ask this question to see how they truly feel about their weaknesses. 

Also, don’t answer with, “are you kidding me? I LOVE that about you!”

Just listen. 

What’s Your Biggest Dealbreaker? 

Hey, we all have deal breakers!

But what’s their biggest?

What Would Make Your Life Perfect Right Now? 

Ooooh, check you out with the suggestive questions!

This question will give you a clue as to what their biggest priorities are right now. Is it a relationship?

Would You Describe Yourself As A Happy Person? 

This is a fairly introspective question that will really get them thinking. And how do they define happiness anyway?

And is happiness something we should aspire to? 

What Do You Like About Me? 

This seems like an egotistical question, but it’s a great conversation starter because it shifts the conversation from them onto you – kinda

Rather, they’re still doing the talking, but they’re not talking about themselves. And this might help them to open up more. 

What’s Your Favourite Book? 

If they read, this is a no-brainer when it comes to conversation starters. 

What’s Your Favourite Movie? 

To be fair, this question could go two ways. They could give you a one line answer, or they could elaborate on their favorite movie. Which would make this a fantastic conversation starter.

What’s The Best Kiss You Ever Had? 

This could seem like an awkward question but if you two have already broached the subject of kissing, sex and intimacy, it could help to steer the conversation in the right direction. 

Who’s The Most Famous Person You’ve Met? 

Even people who claim to “hate celebrities,” will be able to answer this one. Whether they’ve met a famous actor, music star or otherwise, all of us have met someone famous. 

What Personality Trait Do You Like The Most In Others? 

You can ask this question to kickstart a conversation and to find out whether or not you’ve got the personality they love. 

What’s Your Hidden Talent? 

The thing about our talents is that so many people are usually too modest to talk about them!

Ask this question to get them to open up about theirs. 

What’s The Strangest Thing About You?

Maybe they have eleven fingers, webbed feet or a hair back?

Where Do You See Yourself In Five Years? 

When you want to get serious and truly get them to open up to you, this is a great question that can inspire endless hours of conversation. 

Naturally, you will need to share where you want to be in five years time, too. 

What Superpower Do You Wish You Could Have?

Everyone wants to be invisible – but what would they do with it? 

If Money Was No Option, Where Would You Live Right Now? 

This is a really great question that can get the two of you dreaming about a dream life together! 

What’s Your Biggest Regret? 

People don’t always want to talk about the things they regret, which is fine. But if they’re comfortable talking about this subject, you could end up learning much more about them. 

What’s The Most You’ve Ever Spent On Something?

Be prepared to wince! 

Are You Happy With Who You Are? 

Is anyone truly happy with themselves? Who knows? Asking this question could certainly spark a deep, involving question about what it means to be happy. 

Would You Go Into Space? 

Who wouldn’t?!

No, seriously, it’s well worth finding out where they stand on this one.

And do they believe in aliens, perhaps?

What’s Your Happiest Ever Memory? 

I mean, this is a HUGE question that they might have to think about for a bit.

Or maybe they already know what their happiest ever memory is.

Either way, it will make them all warm and fuzzy inside to share it.

After all, who doesn’t wanna feel happy? 

How Do You Deal With Arguments? 

Arguments happen. It’s how we react to them that matters. Finding out how they deal with arguments will tell you a lot about them, as well as how the two of you will get along. 

What Are You Most Proud Of? 

Maybe they won’t want to talk about themselves, in which case you can skip this question. But if they don’t mind talking about themselves, this kind of icebreaker can be the perfect way to talk about the things you’re both proud of.

Do You Like To Take Risks? 

And if so, what kind of risks? What are their limits? 

Was There One Thing That Changed Your Life? 

It’s often the case that we experienced a life changing moment. Speaking about it and sharing it with others can be incredible. 

Who Can You Always Rely On? 

Get them talking about the people that really matter in their life. It always works. 

What’s The Hardest Thing You’ve Ever Done? 

Maybe they broke up with the love of their life, quit a really good job? 

Either way, this question is an excellent conversation starter. 

What Does Your Perfect Life Look Like? 

Oh damn, this question will get them thinking! If there’s one thing people love to talk about it’s their perfect life. 

What Opinion Do You Hold That Others Would Think Is Controversial?

Whether or not they’re ready to answer this question just yet depends on how well the two of you know each other. But if they decide to answer it, this question could spark an interesting discussion!

Is Money Everything? 

Money is a fascinating subject and everyone has an opinion on it. Could theirs be the same as yours? 

Did You Think Your Life Would Turn Out This Way? 

This is a really open-ended conversation starter that could lead in all different kinds of directions, including hopes and dreams, ambitions, regrets and more. 

Do You Think Social Media Is A Good Or Bad Thing? 

Like money, everyone has an opinion on social media, and discussing it could easily see the two of you head down a rabbit hole whereby you cover all kinds of topics, from technology to politics. 

What’s Your Biggest Success? 

They might be too modest to brag, but there’s nothing wrong with the two of you celebrating their successes in life! This question also gives you a chance to learn more about the good things they’ve done so far. 

What’s Your Biggest Failure?

This might seem like a harsh question, but failures teach us how not to do things. What do they consider to be their biggest failure and how have they learned from it? 

Are You In Your Ideal Job? 

Some people love their jobs, some absolutely hate it. Either way, many of us love to talk about it, including the work we do, the boss we love or hate, as well as our colleagues!

What’s The Best Piece Of Advice Anyone Gave You? 

And maybe they can share some of that wisdom with you. 

What Conspiracy Theory Do You Believe? 

Ooooh, if ever you wanted to have a conversation about strange and weird things, this is the question to ask!

Do You Prefer To Spend Or Save? 

The thing with this question is that it doesn’t require a simple Yes or No answer. Instead, it gives you the chance to delve into topics like finances, discipline when it comes to money (and anything), and addictions (clothes!). 

Do You Have Any Annoying Quirks?

We’ve all got ‘em – but will they be willing to share theirs? 

Are You An Introvert Or An Extrovert? 

There’s no simple answer to this question, and whatever they say will require a fairly lengthy explanation!

What Are You Most Passionate About? 

Invite them to open up to you about their passions and share in their enthusiasm. 

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