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Your Go-to First Date Questions

photo of Laura
by Laura
Your Go-to First Date Questions

Picture the scene: you’re on a first date, you’ve got sweaty palms and you’re experiencing a deep-seated terror of not having enough to talk about and being plagued by awkward silences. If only there existed a list of carefully selected go-to first date questions gathered by Match, I hear you cry.

Well, you’re in luck! Here we’ve put together our top suggestions for first date conversation starters, from the frivolous to the serious, via the deep and the downright weird. Whether you’ve met on a dating site or through friends, our guide should give you plenty of inspiration to ensure the conversation never runs dry.

Light-hearted questions

The perfect starting point for any first date: use these questions to break the ice and begin to get to know your date on a basic level.

  • What’s your favourite book/movie? A real classic first-dater, this is a quick insight into how much you might have in common.
  • What would your ideal weekend be? See if their idea of fun matches yours and get a taste of what makes them tick.
  • What did you dream about last night? Try to phrase this as non-creepily as possible. Dreams can be massively revealing. Your date’s subconscious might tell you something you wouldn’t have touched on otherwise
  • What’s your happiest memory? Who doesn’t love talking about the time when they were happiest? Gauge whether you and your date have similar ideas of what it takes to feel fulfilled.
  • Which 3 people would you invite to a dinner party and why? Dead or alive, they can opt for anyone they find inspirational or would love to grill (metaphorically of course).

Funny questions

If you feel your date needs an injection of laughter, whip one of these out. Let the funny stories flow!

  • What’s the best joke you’ve ever heard? Another classic question. Hopefully your date will have one up their sleeve to make you chuckle or groan, depending on its quality.
  • What’s the most outrageous thing you’ve done when drunk? Your date might not be willing to admit to their very worst drunken antics on the first date but you should be able to extract some funny stories at the very least.
  • Would you rather fight 100 duck-sized horses or 1 horse-sized duck? The original would you rather question. Feel free to expand on this and head further into would you rather territory, but try to avoid anything too unsavoury unless they’re into it.
  • What crime are you most likely to be arrested for? Hopefully you’ll be given an amusing answer rather than a heartfelt confession.
  • What popular combination of food grosses you out? Maybe they can’t stand pineapple on pizza, are revolted by fruit and meat being put together, or just don’t get peanut butter and jam. Everyone has a food-related pet hate, so let them out and find out if your tastes are compatible.

Deep questions

Every date should have its fair share of profound conversation, as long as it’s balanced out with more trivial chat. Drop some of these questions into the discussion to encourage a more philosophical side to your first date:

  • What happens after you die? Whether they’re a fervent believer in the afterlife, reincarnation, or are simply undecided, this is a thought-provoking question which might lead to you re-examining your own beliefs.
  • Do you think there’s alien life out there? No one really knows the answer to this question, which makes it a fascinating one to ponder.
  • What ethical consideration is most important to you? A great question to get right to the heart of your date’s outlook on life. This probably affects everything your date does, so if you disagree it could be a dealbreaker.
  • What one piece of advice would you give to your 18 year-old self? We could probably all formulate endless lists in response to this question, but narrowing it down is tricky. Your date’s response will give you an idea of what they were like at 18 and how much they’ve matured since then.
  • What’s the biggest lie you’ve ever told? Let’s be honest, your date’s unlikely to be completely honest in response to this one. Use their response to try and gauge how sincere they’re willing to be with you.

Personal questions

In a similar vein to deep questions, this selection is a fast-track to getting on intimate terms on a first date . It’s probably best to avoid reeling all of these off at once, or the date will risk turning into a counselling session.

  • Do you get on well with your parents? No one has the perfect family life, as hard as we might try to portray this on social media. Find out what their family dynamic is like and share your own anecdotes.
  • Who has had the greatest impact on your life? It might be a celebrity, or their darling grandma. Either way, this person is important to them and you should take an interest.
  • What would you change about your personality? If they answer honestly, they’ll feel vulnerable when admitting their faults. Show them you appreciate this and respond in kind.
  • When did you last feel genuinely scared? People also feel vulnerable when they’re scared. Get your date to open up on the first date by admitting to times when they’ve felt this way, for whatever reason.
  • Are you happy with your life at the moment? This could elicit a more or less honest response from your date. If they’re going through a bad time they might not want to share this with a near-stranger, but it might be exactly what they need. If they’re in a great place you can find out why and learn more about their motivations.

Risky questions

Tackle these at your own peril! These may or may not go down well depending on how your first date is going. Use your judgement and don’t hold us responsible if they cause the date to take a nosedive.

  • How many people have you slept with? If you can’t control your curiosity, go ahead and get this one out of the way. Just remember not to judge; it was you who asked!
  • What are your political views? This can open a real can of worms, although some might say that it’s better to lay your cards on the table as soon as possible.
  • Do you fancy that person over there/the waiter/waitress/anyone else in the room who isn’t me? If you get the impression that your date is more interested in someone else in the room than you, it might be better to stop beating around the bush and just ask.
  • Why did you and your ex break up? Even broaching the wider subject of previous relationships can be risky. Asking this question may result in tears, a long rant or perhaps an honest conversation. Who could say for sure?
  • What are your views on vegetarianism/veganism? Another topic which can be super divisive! If this is an important issue to you you’ll probably want to address it on the first date, but be prepared that this might kick off a debate and you could end up leaving cursing all meat-eaters.

Find out daters’ opinions on how soon to message after the first date, or check out why you should always go for coffee. Or, sign up with Match to put these questions into practice on a first date with someone new!