10 Questions to Ask Your Match for More Meaningful Conversations

Sending that first 'like' can feel scary. But when they like you back? Now comes the part that can somehow feel even scarier: figuring out what to say.

You want to sound interested, but not too interested. You want to ask something better than “How’s your week going?” without sounding like you pulled a question from a job interview. And while you’re thinking about the perfect opening line, suddenly, 20 minutes have passed and you still haven’t sent anything.

Here’s what we’d tell a friend: stop trying to say the perfect thing.

A good conversation doesn’t need a clever opening line. It just needs somewhere to start. Ask something you’re genuinely curious about, pay attention to the answer, and let the conversation go from there.

If you need a little inspiration, here are 10 questions we’d actually recommend asking your match.

1. What’s something you’ve been really into lately?

This is basically the better version of “What do you do for fun?”

Maybe they’ve become weirdly invested in pickleball. Maybe they’re watching a show you love. Maybe they’ve been trying every ramen spot in the city.

Whatever they say, you’ve got something real to talk about, and an easy follow-up: “Wait, how did you get into that?”

2. What does your ideal weekend look like?

Trust us, this tells you way more than you’d think.

You get a little peek into what their life is actually like when they’re not working or answering dating app prompts. And, more importantly, you can start to see whether the way they like to spend their time meshes with yours.

3. What’s something you could talk about for hours?

You know how someone gets instantly more interesting when they start talking about something they really love? That’s what you’re looking for here.

You don’t even have to care about the same thing. Half the fun is seeing what gets them excited, and maybe discovering a side of them you wouldn’t have gotten from their profile

4. What’s the best thing you’ve eaten recently?

Food questions are basically impossible to mess up.

They’re easy to answer, they don’t feel too personal, and somehow they always lead somewhere, to favorite restaurants, travel stories, family traditions, or very strong food opinions. And if you happen to discover a place you both want to try, well, there’s an idea for a first date.

5. What are you looking forward to right now?

This is one of those questions that feels light but tells you quite a bit.

Maybe they’re counting down to a big trip. Maybe their favorite artist is coming to town. Maybe they're just excited to sleep in this weekend.

Either way, you're learning what makes them excited, and that's usually much more interesting than asking how their Tuesday went.

6. What’s a small thing that always makes your day better?

You don’t have to ask someone their deepest fear to learn something meaningful about them.

Sometimes the tiny things tell you more. This question gets you past the résumé stuff and into those little details about someone that you might actually remember a few dates from now.

7. What’s a hill you’re willing to die on?

Okay, enough being serious. Let them have an opinion.

This one gives you an excuse to tease each other, disagree a little, and show some personality. Because if your chat is starting to feel suspiciously like an interview, a little playful debate might be exactly what it needs.

Just maybe save politics and whether their ex was actually the problem for later.

8. What’s something you want to try but haven’t yet?

This is our sneaky way of asking about what they want out of life without hitting them with “Where do you see yourself in five years?”

You get to learn what they’re curious about and what kinds of experiences excite them. And if you both say, “Wait, I’ve wanted to do that too,” you may have just made planning a future date very easy.

9. What’s something people are usually surprised to learn about you?

Because their profile definitely isn’t telling you everything.

This gives them the chance to share the side of themselves they actually want you to know about. And unlike asking for a random “fun fact,” there’s usually a story behind the answer, which is exactly what you want.

10. What would make you excited to go on a first date with someone?

If you’ve been talking for a while and the vibe is there, you’re allowed to be a little obvious.

Instead of guessing what kind of date they’d enjoy, just ask. You’ll learn something about them, make your interest pretty clear, and, if you’re both feeling it, give yourselves a very easy opening to actually make plans.

Please don't ask all 10! 

Seriously. This is a conversation, not an interview.

These questions are here to get things started, not to work through one by one. If your match says something interesting, stay there. Ask a follow-up question. Share your own story. Let the conversation go somewhere you didn’t plan.

If they tell you they spent every summer growing up at their grandparents’ house in Italy, don’t respond with, “Cool! Anyway, what’s a hill you’re willing to die on?”

Ask them about Italy. Find out what made those summers special. Maybe it reminds you of something from your own childhood. That’s the good stuff.

The best conversations happen when you stop thinking about what to ask next and start paying attention to what they’re telling you.

And if your mind still goes completely blank...

You know the feeling. You open the chat, start typing, delete it, try again...and somehow “hey” is still the best you’ve got.

Don’t overthink it. 

That’s exactly why we made Topic Suggestions. If you’re not sure what to talk about, we’ll give you a little nudge to help get things going.

Think of us as the friend sitting next to you saying, “Wait, ask them about this.” We’ll help you break the ice, and you take it from there.

And remember, a good conversation doesn’t have to be deep to be meaningful. Be curious. Ask the follow-up. Go off topic. Tell the story that their story reminded you of.

You don’t need to say the perfect thing. You just need to give them something to respond to.