What to Talk About on a Date, According to Expert Matchmaker

Hot take: forget whatever they told you about what to talk about on a date. Mindful dating means taking into account what the recipient of your questions might be thinking or feeling in response–so try to get a feel for the audience before going in hard–but ultimately, your questions aren’t just about their responses, but also of the values and interests that fuel the questions themselves. It’s okay to be you. Start there, please.

First date conversation topics, in best practice, might have an air of lightness to them, but that still allows you space to have playful, meaningful and dynamic discussions. Let’s keep that in mind as we go through some creative options to break through ice. Caution: interview dates are the devil and can put you in an automated and uncomfortable state. 

We’re offering you some conversation topics for creative and dynamic conversation, ideally not sat across from each other with laptops. It is possible that you’re still doing this via text, though, so a solid foundation of dating acronyms might also come in handy. In either case, take just a few, and enjoy. 

Funny Questions to Ask Your Date

“A merry heart really does a spirit, soul and body good like medicine,” someone important said once.

We offer this first because a first date, especially, might offer a ton of opportunities for the awkward or less ideal. Your un-attentive waiter, the noisy atmosphere, or pregnant lapses in conversation might best be combated with a conscious effort to have fun. No rules here, but it would be good if you could come up with an answer for each of these, too, and here’s a few options: 

What’s the funniest thing that’s happened to you recently?

This question allows your date to share an anecdote of their own and hopefully reveals their brand of humor a bit. Worst case scenario here: be prepared to accept an un-funny answer. That might be funny too.  

If you could have any superpower, what would it be and why?

Superpower choices can reveal a lot about a person’s personality, what they long for, and what their sense of adventure looks like. 

What’s your go-to karaoke song, and could you give me a preview?

Karaoke questions can lead to hilarious revelations and maybe even a duet later in the evening.

If you were to win the lottery tomorrow, what’s the first absurdly extravagant thing you’d buy?

A little bit of fantasy and dreaming can go a long way, and lead the conversation further into deeper places.

What’s the most embarrassing or absurd thing that’s ever happened to you on a first date?

So long as it’s not “all of these questions you’re asking,” this offers a great window into their personality and a place for you both to share. 

Serious Questions to Ask

It could be the New Yorker in us to go in head-first, here, so you might qualify some of these date topics and ask first if your date might be into going a little deep. Be prepared to share your own answers first, in either case, so you can lead by example. The truth is, a lot of these questions don’t feel so strange to answer, but will be missed by the unintentional dater for fear of seeming too intense. Consider using these powerful and timeless options sparingly and with grace: 

What are your core values, and how do they influence your life decisions?

Again: a little intense, maybe. Be prepared to share first, if you want them to take the plunge. 

What is the most significant life lesson you’ve learned so far?

This question invites personal reflection and can lead to insightful conversations about where your person has been, where they hope to go, and what you might share with them. 

Where do you see yourself in five years, and what steps are you taking to get there?

The most interview-esque of all interview questions. Know that not everyone thinks linearly or even does this, but a lot of people really do. 

What are your green flags and yellow flags? Red flags? Dealbreakers?
Evolution and society has got us all looking for signs of danger and safety. Signs of chemistry, strangely, can often be found in the things you mutually reject and why. Don’t be afraid to discuss the taboo and the dealbreakers

Questions to Ask if They’re Shy

We might have gotten ahead of ourselves. Sometimes a slow and steady intro is best, and not everyone wears their heart on their sleeve. These “back to basics” are still worth taking a look at when you’re looking for first date conversation starters. 

What are your favorite hobbies?

Shy people often feel more at ease discussing their own interests and passions; this is a low-budget order for vulnerability, and offers you a space for connection and conversation.

Do you have any favorite books or movies?

Shared interests in literature or cinema can lead to engaging discussions and common ground. Note: this is a great pick if you’re unsure of moving forward and looking for low-hanging and friendly date topics for you both.  

Tell me about a place you’ve always wanted to visit.

A top pick. This question allows them to dream a bit and give you both a space to talk about your travel aspirations, and where you’ve both already been.

Thought-Provoking Questions

If you’re looking for something a little headier, we’ve got you covered here, too. These are great questions to check on your match’s EQ, or emotional intelligence, if that’s something you’re after understanding. 

If you could have dinner with any historical figure, who would it be and why?

This question can lead to intriguing discussions about history, upbringing, values, and role models. It’s worth knowing: a lot of these answers are often highly identity-based. 

What’s the most challenging decision you’ve ever had to make?

Delving into decision-making processes can reveal a lot about a person’s character.

If you could change one thing about the world, what would it be, and how would you do it?

This question can uncover your date’s passion for social change, their take on the world, and their orientation toward problem-solving.

Questions to Deepen the Connection

Let’s say it’s going well. Here’s a number of questions your matchmaker might have already touched on, though, to establish core compatibility. We’ll give them to you for free. 

What’s your love language, and how do you express affection?

Understanding how your date gives and receives love can foster a more harmonious relationship, and if you’re not familiar with these “top five” answers, google it together for a little fun!

What qualities do you value most in a partner and why?

This question helps align expectations and highlights shared relationship goals.

Can you describe your perfect day from start to finish?

Sharing ideal days can help you envision future experiences together. Comparing your answers offers a lot of room for back-and-forth. 

Questions to Ignite Passion and Creativity

If you’re looking to add a dash of excitement to your date, consider these questions that tap into your date’s passions and creative side:

What’s a hidden talent or hobby you haven’t shared with many people?

This question encourages your date to reveal a unique aspect of themselves.

If you could live in any era of history, which one would it be, and why?

Exploring historical preferences can lead to interesting discussions about culture, perspective and lifestyle.

What’s the most adventurous thing you’ve ever done, or would like to do?

Sharing adventurous stories and dreams can ignite a sense of excitement and wanderlust.

Questions to Gauge Compatibility

Compatibility is a vital factor in any lasting relationship. These questions can help you assess whether you and your date are on the same wavelength:

How do you handle conflicts or disagreements?

This question provides insight into communication and conflict resolution styles. Pro tip: the way people handle work, family, and relationships are not all the same, but there’s often a ton of pragmatic overlap. Talk about that!

What role do family and friends play in your life, and how important are they in your relationships?

Understanding the importance of relationships can reveal your date’s key priorities.

What’s your stance on personal growth and self-improvement?

Shared goals for self-improvement can strengthen your connection and support mutual growth, and a really zealous or totally underwhelming answer could be great info for you moving forward. 

Questions for Playful Bonding

Creating shared memories and inside jokes is a fantastic way to bond with your date. Try these questions to foster playfulness:

If we could embark on a spontaneous adventure right now, where would you want to go?

This question can lead to impromptu plans or spark exciting travel fantasies.

What’s your guilty pleasure when it comes to food, and would you dare me to try it?

Bonding over foodie culture can add a delightful twist to your date, and expose you to cuisine you might never have thought or heard of before.

If you could switch lives with any fictional character for a day, who would it be and why?

Imagining life as a beloved character can be a whimsical and entertaining exercise.

Questions for Future Planning

As your connection deepens, it’s essential to discuss future plans and aspirations. These questions can be great first date conversation starters to help you align your dreams:

What are your top three bucket list items, and how do you plan to accomplish them?

Sharing bucket list goals can inspire mutual support and adventure.

How do you envision your ideal partnership, and what are your non-negotiables in a relationship?

Discussing relationship expectations can lead to more profound connections.

What are some activities or hobbies you’d like to explore together in the future?

Planning future adventures together can strengthen your bond and create shared excitement.

There’s a lot of potential for over-thinking when asking ourselves what to talk about on a date. We live in pockets of culture, politics, and socio-economic status. Your and your date’s answers to these questions will invariably contain information about all of those things, but our perspective on dating is about human connection and foundation building from start to finish.

We care about conversation topics that build bridges and encourage shared perspectives.

We’ve had first dates end at first dates and marriages. We’ve also had first dates end in shared businesses and lifelong friendships. And we’re here for literally all of that. What to talk about on a date is up to you, but what sticks is what’s most important.

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