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The First Date Questions You Should Be Asking

by eharmony Editorial Team - June 13, 2024

A first date can be a daunting prospect. Pre-date nerves make us worry about what we’re going to say. We forget it’s just meeting another person and having a conversation, and turn it into a grand test of general eligibility. So it’s perfectly understandable to be nervous and overthink things.

There are ways to calm your nerves though. As conversation is the centerpiece of any date, it’s always good to prepare some first date questions. Take a look at our list of questions to ask on a first date and maybe you’ll find a little inspiration, and perhaps confidence.

What do you talk about on a first date?

Whoever said first dates are like interviews probably went on a few too many. That’s not how first dates work, nor should it be your mindset when coming up with first date questions. After all, you’ve likely exchanged a few messages already and gotten to know each other somewhat during the process of setting up the date. So you’re not starting off as complete strangers – unless it’s a blind date.

A first date is a simple test to check if you have any real-world chemistry and to talk more about the things that matter: how you live your life, future aspirations or even favorite movies. You’re trying to get a gauge on that tricky notion of compatibility. So it’s mix of trying to have fun, examining whether you’d fit well together and seeing what your heart tells you in the moment. You should focus on how do you keep the conversation flowing on a date? 

But you’re also going to be checking for compatibility. Do you have anything in common? Do you want the same thing right now? How do they feel about their career? These are questions you can’t just ask one after the other like they’re being formally vetted. So good first date questions should blend the enjoyable aspects of conversation, from inquiring about their life to hashing out generally popular topics of the day to just having fun and a few laughs.   

While coming up with a list of first date conversation starters may sound like it could take away from the organic aspect of getting to know someone, we all know sometimes the conversation just experiences a natural dip. It is a first date, after all, so awkward silences come with the territory.

Having a loose list of interesting questions to get the energy back isn’t being insincere so much as admitting you’re a normal person who sometimes can’t figure out what to say next. 

Ways to be Less Awkward on a First Date

There’s no denying that first dates can be awkward. We tell you about why we feel akward, how to turn an awkward date around and how to build confidence for less awkward first dates.

20 good first date questions

Try to come up with your own questions for a first date, basing them on the individual person and what fits with your personality. This not only makes them seem more natural but it also shows your date that you’ve taken an interest in what little you know about them.

So here are some good first date questions beyond “So what do you do for work?”, that can fit either a casual or funny mood, which you can use as guidelines and adjust to the context of your date’s general vibe. You should use these prompting questions as a springboard into a larger conversation, so make sure to ask follow-up questions based on their replies. 

Casual first date questions

When the date is just starting, keep the conversation casual until you’re more comfortable with each other. These questions will help keep the conversation light and engaging:

  • What adventurous thing have you always wanted to try?
  • How do you deal with your work-life balance?
  • What’s one skill or interest you wish you’d worked more on?
  • If you never had to work again, what would you spend your life doing?
  • What are your friends like? What do you like doing when you get together?
  • If you had to recommend only one podcast/movie/book, what would it be?
  • What’s the first concert you ever went to?   
  • What was your first impression of me when you saw my profile? (if you met online)
  • You’re at a karaoke bar. What’s the first song you’re singing?
  • What’s your favorite place in the world you’ve been to so far?

Funny first date questions

If the vibe is more light-hearted or maybe you just want to try to make your date laugh, you could try these quirkier first-date questions.

  • What was the weirdest thing about the town/neighborhood you grew up in? 
  • Do you prefer going out to restaurants or just takeout and TV in your pajamas?
  • What was the story behind your worst first date? And please don’t say it’s me.
  • What TV or movie universe have you always secretly wanted to live in?
  • If you’d never met me before, what would you guess my name and occupation is?
  • What song lyrics did you get wrong for years until someone noticed?
  • What’s something that always makes you cringe?
  • What’s a secret talent you have but never show to anyone?
  • What’s the craziest lie you ever came up with as a child?
  • What’s one fashion trend you wish would come back?

This is just a short list of suggestions that can help you keep things moving on your date. If you’d like to read more questions to ask on a first date or in other stages of dating you can check out our full article on the topic.

Man and woman sitting on bench looking at each other as symbol for first date tips

Explore first date tips – make the best of your experience

Get some first date tips to help you make a real event out of it, how to make a good impression and quickly find out if they’re the right one for you.

There’s nothing wrong with preparation

Opportunities to meet the right person are all around you. So take charge of your love life and don’t let date anxiety or simple nerves stop you from asking out that special someone.

And there’s nothing wrong with a cheat sheet of first date questions. Often, just making these tiny preparations can make you feel at ease and more confident. It’s all about building up your confidence to get out there. You might very well end up having such good chemistry that you won’t even bother needing them.

One place you don’t need to worry about chemistry is on eharmony. We match you with relationship-seeking singles whose personalities suit yours based on our Compatibility Matching System. And with features like advanced match filtering, richly detailed profiles and Icebreakers, you can get to know people better before you meet up, so there’s even less chance of you needing that list of questions. So why not try meeting someone new today, someone you can be yourself with? Register for eharmony and get who gets you!   

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