21 Questions to Ask on a First DateDating Advice 

21 Questions to Ask on a First Date

I’ve always found the idea of first dates fun… up until it’s time for the actual date, when my brain stops functioning and I come across like a drunken, blithering moron. Whole words escape my mind, and you can forget about full sentences! That’s why I’ve decided to put together the 21 questions to ask on a first date, which are great for getting the conversation started, flowing, and definitely not boring.

21 Questions to Ask on a First Date

Now, I’m not tooting my own horn or anything, but I’ve been told that first dates with me are “great,” my conversation is “captivating,” and talking to me is “so much fun.” I’ve also been on more first dates than I care to remember. So, add the two together, and I decided it was time for me to jot down the 21 questions to ask on a first date that always work for me!

Let’s get right to it.

 

1: What’s the weirdest fact you know?

I’ve learned the weirdest shit by asking this question, some of which I still don’t understand – and it’s a great way to get into the mind of your date and find out what they think is weird/strange/fascinating, etc.

If I were to answer this question, I’d probably say:

You would drown quicker in freshwater than salt water, because the salt helps you to float and avoid drowning for longer. This, in turn, allows you to seek out/call for help. Longer drowning time means longer potential help time!

Not exactly a fun fact, but I found it weird.

 

2: Do you think aliens are out there?

I love a good alien chat, and I also love hearing other peoples’ thoughts and opinions on the subject, too. And it’s a great topic for branching into other topics, such as science fiction movies or books, astronomy, astrology (if you’re into that kind of thing,) conspiracy theories, and more.

*puts tin hat on*

I think that we (humans) are deluded and ignorant if we think that we’re the smartest thing that our universe has to offer. So, yes, I do believe in “aliens” – but not the little grey men-style aliens.

 

3: Where do you see yourself in five/ten years?

If you want to know if your future goals align with your dates’, this question is a great gateway to that subject. There’s no point in chasing a relationship with someone who wants to be single and travelling the world in ten years’ time if your dream is to settle down with three kids and a white picket fence, is there?

Where do you want to be in five or ten years’ time?

Does that dream align with the dreams of your date?

 

4: What’s a movie you’ll always watch if you see it on TV?

You know when you’ve seen a movie one thousand times, but you still watch it when you flick past it on the TV? I want to know about those movies, not your favourite ones. Pretty Woman always captures my attention, and the same goes for Final Destination, the Resident Evil movies, all the Jurassic-whatever movies, and 99% of movies starring Angelina Jolie.

How about you?

 

5: Do you believe in climate change?

This one separates the wheat from the chaff, let me tell you. I’m very much Team Climate Change and Global Warming, so I’d just laugh in the face of someone who didn’t also believe in it.

I’ve already dated Mr. Anti-Global Warming, and it’s not something I’d like to repeat.

 

6: What’s the worst movie you’ve ever seen and why?

Fuck telling me about your favourite movie; tell me about the shittest movie you’ve ever seen, then tell me everything you hated about it. I love a good bitch session, and what better way to bitch in a semi-subtle way, than with movies?

Spider with Ralph Fiennes was a weird one for me. I never really understood it.

 

7: What’s the strangest thing that’s ever happened to you?

Once upon a time, I was walking through a subway in the shithole that is Southend-on-Sea, when a man came up to me and opened his literal trench coat. I thought he was going to flash me, but instead, he offered to sell me a joint… of beef.

I’ve experienced some weird shit, but that might have been the weirdest.

 

8: What is your worst habit?

You might as well get to the stuff that’s going to cause the most fights, right at the beginning. Does your date chew their nails? Chew loudly? Chew in their sleep? Pick at their toenails? Pick their nose at traffic lights? Fart with abandon?

Chances are, neither of you are going to admit to your most embarrassing and worst habits that early on in your dating journey – but who knows what might come up instead?

 

9: What’s something that you’re super proud of?

This is another of those questions that really can tell a lot about a person – and also what their goals, dreams, and aspirations are in life. For example, if someone is proud of earning a high figure, money is something they value and place importance on. Not always, of course, but quite often.

If, on the other hand, they provide more of a giving answer, such as volunteering or doing something for charity, you’ll know that they do know how to give… at least a little.

 

10: How – exactly – would you define cheating?

This is one of those questions that every relationship should define and answer, but so many don’t, which, in turn, leads to a whole host of questions.

Would you be mad if your partner kissed someone else? Fucked someone else? Or is ethical non-monogamy more your thing?

Those limits and boundaries are important, and you shouldn’t just assume that your partner follows the same rules and guidelines for a relationship that you do.

 

11: What scares you?

What happens if you’re both deathly afraid of rodents? Who’s going to get rid of the rodents, should they get inside the home? What if you’re both scared of spiders? Or snakes? Or being alone?

If you’re lucky, you’ll get a partner that can deal with your weaknesses – and vice versa. That’s not to say that it can’t work out, though. You’ll just have to find someone else to deal with the things that you’re both afraid of.

 

12: If you could eliminate one task in your daily life, what would it be and why?

I would personally like to eliminate any kind of dishwashing, so if I’m on a date with a fellow dishwashing-hater, we’re going to need to get a dishwasher, if we ever move in together; otherwise, those dishes are going to stack up real quick.

 

13: What would you be most likely to go to jail for?

Hopefully, neither of you will actually end up in jail, but if you were to get imprisoned for something, what would it be? I think, for me, it would probably be getting mouthy with someone, then ending up in an accidental fight that I will inevitably lose.

How about you?

 

14: Tell me a secret that you usually don’t share

How about a little trust exercise, just for fun?

I always ask a potential date to tell me a secret that they usually don’t divulge, and more people than you’d think happily agree to spilling the beans. Chances are, they’ll tell you something small but still private, which means that you’ll start to get to know them on a deeper and more meaningful level.

 

15: What’s your biggest dealbreaker?

Dealbreakers are funny things, because they’ll often evolve as you meet new people and have new experiences. For me, right now, my dealbreakers would be:

Smoking – because I’d start smoking again, and I don’t want to have to quit again.

Drinking – although, with the right person, I’d be willing to compromise.

Lying (obviously.)

Cheating (again, obviously.)

But what you? What are your dealbreakers? What about your date’s?

 

16: Without ask any further questions, what would you cook me for dinner?

I always ask this question as a test, of sorts, to see if my date has been paying attention. I’ll usually drop little food hints and questions into the conversation, such as, I’m a vegetarian, I don’t like tomatoes, onions make me heave, etc.

If my date then suggests cooking me spaghetti bolognese with fresh tomatoes and onions, I’ll know that they haven’t paid attention to a single word I’ve said. Or y’know, written.

 

17: What’s the last thing that make you howl with laughter?

For me, it’s a fart video on Instagram. If fart videos – and laughing at farts – make me childish, then you’d best know that I’m childish as fuck.

My sense of humour could probably be described as weird, childish, dry, and stupid. I want someone who has a sense of humour that matches mine. This question, I think, separates the contenders from the… well, not contenders.

 

18: Have you ever been in love?

I think this is a great question to find out a few things, including:

  • if your date falls in love at the drop of a hat… and out of it
  • what love means to them
  • If they’re a liar (social media stalking usually reveals the truth)
  • if you’re one of a long line…

 

Do you see where I’m going with this?

 

19: What is your biggest pet peeve?

I leave crumbs in the bed, I sometimes rarely sleep, I need more “alone time” than the average person, and I’m a workaholic. If those things are your biggest pet peeves, there’s no way that our relationship is going to work.

Well, unless you’re willing to massively compromise…

And that rarely happens (to me.)

 

20: Where would you go/what would you do in a zombie apocalypse?

I need to hold my hands up to something before I explain number 20 on my list of 21 questions to ask on a first date: I’m a bit of a mad prepper. Like, a half-prepper. Fairly convinced that a zombie apocalypse isn’t going to happen, but not convinced that humans aren’t really evil, flesh-eating monsters deep down – that kind of prepper.

I’m looking for the kind of partner who could help me in an apocalyptic-style scenario, not hinder me.

If you’re shit in a ridiculous emergency, you just ain’t for me.

 

21: How would your friends describe you in five words?

There is no better way to get to know the real someone, than by getting to know them through their friends. How would your friends describe your date? They’re the people who know them the most, right? How would your friends describe you?

My friends would describe me as:

  1. Annoying
  2. Solver (of problems)
  3. (Too) honest
  4. (Inappropriately) funny
  5. Clumsy

I know that because I asked them. Five of them, to be exact, with one word each. I’m not sure how I feel about “annoying,” but I can’t really argue against it… because I am.

 

Questions to Ask on a First Date: Final Thoughts

What can you talk about on your first date, without research, for five minutes straight?

Start a conversation about that!

Then, ask your date that exact same question: what can you talk about for five minutes without stopping?

Chances are that particular subject is a hobby, work topic, or something you’re passionate about – and what better way to learn if your hobbies and interests play well with your dates’?

As a side note, psychologist Tiare Tolks, speaking with Capsule NZ, says: 

“I’m a big believer in a side-by-side date, rather than face-to-face,” she says. “It just takes an element of the intensity out of it when you’re not sitting across from each other, looking directly at one another.”

 

21 Questions to Ask on a First Date

 

Summary: Questions to Ask on a First Date

And that’s that, folks: 21 questions to ask on a first date that will help you get to know them, have fun with them, and open up many more conversations!

Don’t forget to come back and let me know how the date goes, if you use these questions! Obviously, I sure hope it goes well.


Thanks so much for reading my blog today! 🖤

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