Here at Timeleft, we're big believers in one thing: showing up.

And the quickest way to make that count? Through IRL conversation, of course.

For many (most) of us, though, the thought of enduring unwanted small talk is enough to put us off from showing up in the first place… luckily Timeleft events, where everyone showed up for the same reason (and with built-in, in-app conversation starters), tend to foster great conversations that don't stay awkward for longer than ±5 mins*.

*It must be noted that any awkward silence is almost always followed by shared laughter.

Take these Timelefters as proof:

The thinking behind building our in-app conversation starters was the importance of conversation – when you only have an hour or two to get to know someone at any given event, asking the right questions matters. Those first few minutes of meeting another Timelefter will pretty much determine how the rest of the time together goes. So why not go in with a coupla good ones up your sleeve?

Before we get into them though, we must just point out the one single guiding golden rule of conversing (for introverts, extraverts, and ambiverts alike):

The most important thing for any conversation is genuine curiosity

If you follow that, then you’re well on your way to a great (and genuinely enlightening) conversation. Pair the above mindset with the questions below, and you're set. They work in any setting too – work, family gatherings, weddings… you name it.

Why the right questions matter

Asking good questions is more important than we might like to think. Psychology tells us that first impressions form within milliseconds, often before a word is even spoken. In settings where you only have about two hours together, that window doesn't get much longer. What you ask in those first few minutes will largely determine whether or not you see this person again (no biggie).

If you've ever wondered what exactly to ask, here's our general recommendation:

Embrace open-ended questions that invite a story, not closed questions that get you a yes or a no. This is because they encourage people to actually think and share, surfacing opinions and feelings rather than one-word answers.

Closed question: What job do you have?

Open-ended question: What’s your idea of a perfect Saturday?

In a conversation, that depth doesn't just make things more interesting, it's often the difference between a forgettable exchange and one that goes further. The best conversation starters do both – they're easy enough to answer without thinking too hard, and interesting enough to take the conversation somewhere real.

Get to know you questions, grouped by vibe

The best questions are open-ended, a little unexpected, and reveal personality fast. Skip "So, what do you do?" and try "What's the most spontaneous thing you've ever done?" or "What topic could you talk about for hours?"

At Timeleft, we've tested thousands of conversation prompts across 3M+ social dinners worldwide. The questions that consistently spark the best connections? The ones that require a bit of a story to answer. We've grouped our favorites by where you are in the getting-to-know-you journey – early nerves, finding your rhythm, or going a little deeper.

Let’s get into it, shall we?

Light, fun openers (first 60 seconds)

Think of these as the fun questions to ask when you first meet someone – quick-fire icebreakers that break tension fast so you can both get a sense of each other's vibe.

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Tip: If things feel awkward at first, don't panic. Try acknowledging the awkwardness out loud, it usually leads to a good laugh.

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A random fact that you like?

If your life had a tagline, what would it be?

A book or series you'd recommend?

Weirdest thing you’ve ever eaten?

What are you currently obsessed with?

What do you do to switch off?

How do you spend your free time?

Best trip you've ever taken?

What’s a surprising skill you have?

Last thing you did for the first time?

‘Get to know you’ questions (the middle)

Once the ice is broken, you can start asking more thoughtful questions – the kind that invite someone to actually reflect. This is where real personality starts to show.

They also signal that you're genuinely curious, not just filling time. Whether you ask about a formative memory, a strongly held opinion, or something they'd do differently, you open the door to the kind of conversation you’ll both remember.

If your personality was a weather forecast, what would it say today?

If you could uninvent one thing, what would it be?

Would you rather explore the world or make roots in one country?

You have to give a (mini) TED talk right now, what's it about?

What's a rule you live by that nobody taught you?

When do you feel most like yourself?

What did you spend most of your time doing as a kid?

Would you rather give up social media or give up eating out?

Topic you’d cover at a conspiracy theory party?

What's something you'd do every day if you could?

Deep questions to ask (take things further)

Genuine connection requires depth… And while most people steer clear of anything too deep upon first meeting, a well-timed question can take a good conversation somewhere genuinely meaningful without derailing it.

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Tip: If you can’t remember any of these in the moment, simply think about something you value deeply and phrase a question around that.

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What does a life well-lived look like to you?

What's something you'd never compromise on?

A quality in other people that you admire?

Something you're genuinely curious about right now?

What is the kindest thing that anyone has ever done for you?

Something you've stopped apologizing for?

What kind of people make you feel most yourself?

What's something you're proud of?

One piece of advice you’d give your younger self?

What’s one ‘offline’ thing you love doing?

Creative questions (if you want to stand out)

One thing that can be easy to forget during these interactions, is that conversations with new people are meant to be FUN. If you really want to leave an impression, a little levity goes a long way… get creative!

If you could live one day from history, what would you pick?

If you had to delete all your apps except two, what stays?

If your life was a film, what genre would it be?

What's the strangest compliment you've ever received?

What's a smell that immediately takes you somewhere?

What's a movie or song you're embarrassed to love?

If you could only listen to one album for the rest of your life, what would it be?

If you had to eat your way out of a pool of food, what would it be?

*Giving you a permission slip for 1X humble brag*

If I met you 5 years ago, what would be different?

Questions to avoid (save for later)

Not every good question belongs in the first five minutes of meeting someone. These ones aren't “bad” per se, they're just better once you've built a little trust. Save them for meetup 2 or 3, when the foundation is there to answer them honestly.

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Tip: If you wouldn’t speak about it in a job interview, then rather keep it in your pocket for when you know each other well.

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How much do you earn?

Do you want kids?

Why did your last relationship or friendship end?

What's your biggest trauma?

Do you go to therapy?

What are your political views?

What's your religious belief?

What are you looking for in a friend?

How many people have you dated?

Do you own or rent?

How to use these in the moment

Since we're all human and not robots, a lot of what happens when you meet someone depends on chemistry, mood, and how naturally things flow. These questions are a good starting point, not a script. If an answer intrigues you, follow it.

As mentioned at the beginning of this piece, the best conversations tend to grow from genuine curiosity, not a prepared list.

A good rule of thumb: listen more than you talk. It makes the other person feel genuinely heard, and creates the kind of atmosphere where conversation can actually happen. And lastly, match their energy. If someone lights up at a question, follow that thread. If not, move on. Go with your gut. The questions are just the door; what's on the other side is up to you (and a little bit of magic too).

Where else these questions work

Good questions don't expire after first use. Whether you're looking for questions to ask someone at a networking event, a dinner party, or meeting someone for the first time anywhere, the same principle applies:

Depth beats small talk, every time.

At Timeleft, we've built an entire experience around that idea. Instead of a quick chat, you get a full evening of conversation. Instead of hoping you end up next to someone interesting, you get a table of six matched to you. No bios, no swiping, just a great dinner with interesting people… what happens from there?

Well, the table really is full of possibilities.

Ready to put these into practice? Become a member and show up to your first Timeleft dinner this week.

FAQ

What are good questions to get to know someone on a first date?

Stick to open-ended questions that invite a story rather than a yes or a no. The light and 'get to know you' sections above are a great starting point – questions like "What's the most spontaneous thing you've ever done?" or "What's a rule you live by that nobody taught you?" reveal personality fast without feeling too intense. Save the deeper ones for once the conversation has found its natural rhythm.

How do you ask deep questions without making it weird?

Timing and tone do most of the heavy lifting. If the conversation has been flowing naturally for a while and there's a genuine back-and-forth happening, a deeper question won't land as strange, it'll feel like a natural next step. The key is to share something of your own first. Vulnerability is contagious; when you open up a little, the other person usually follows.

What questions should you avoid when getting to know someone?

Anything that feels more like an interview than a conversation – salary, relationship history, political or religious views, or anything that puts someone on the spot before trust has been established. A good rule of thumb: if you wouldn't bring it up in a casual work setting, save it for later.

How many questions should you ask in one conversation?

There's no magic number, but quality always beats quantity. A single good question that sparks a 20-minute conversation is worth more than ten quick-fire ones that keep things surface level. Ask, listen properly, follow the thread, and let the conversation lead you.