Advice

How To Trick People: Into Answering Personal Questions On The First Date

Every once in a while you’ll need to go on a first date, or a blind date, and you’ll have to dance around getting to know each other without crossing the line and becoming too personal. This is easier said than done, and if you’re anything like me you’ll want answers to big questions way earlier than it’s appropriate to ask.

Because I have your back like the true good bitch I am, I have created the below “fun and silly” questions to trick information out of your date. The important thing to remember when asking these is that it isn’t meant to be a quick-fire Q&A – you’re meant to think about the answers, discuss them, and expand on why you’ve chosen what you have for it to actually be useful. Go forth and use them as you see fit. I’m a fucking genius.


  1. If you were an animal, what kind would you be and why?
    Great for insight on how your date sees themselves. 
  2. If you could have any superpower, keeping in mind you don’t get any complimentary powers (eg if you fly you still need to breathe, and you get cold, so you’ll be limited as to how high you can go), what would you pick?
    Find out if they’re a nerd, and more importantly if they’re a nerd who makes bad choices. 
  3. You have won the lottery for $150 million dollars. After taxes this would be $50 million because you have to take the lump sum. Firstly, do you try and avoid the taxes? Secondly, how do you spend your winnings?
    Does your date believe in social responsibility, and if money wasn’t their main motivator what would they do with their life? 
  4. A scientist offers you the chance to be genetically modified and become part human part cat. You won’t get any really cool abilities, but you will get a much larger leap (think 15 metres) and you will get a tail. The tail can be hidden under clothes but functionally you’d have to get creative to use it for anything. Do you report the scientist to the government for human experimentation, or do you go through the procedure? Why?
    What is their opinion on genetic modification? Does how other people think of them affect their choices? How far do they think into the future? 
  5. A baby has a gun pointed at your head and next to you stands your mother, your first love, and your best childhood friend. The baby is definitely going to shoot one of you, as it has to for initiation to the gang “Swooping babies”. What impassioned speech do you give to get the baby to shoot someone other than you?
    Figure out what their relationship is like with the people they loved early in their life. 
  6. You have been captured by locals while hiking in a geographically inoffensive country. Luckily they speak perfect English as it quickly becomes apparent they are going to sacrifice you to their god. You have one opportunity to avoid your overall gruesome death by convincing them that you yourself are a god. How do you do this?
    How creative / how good at lying / how not racist can they be when making up a story? 
  7. It’s August 1846 and your father has wasted your dowry on booze and gambling. There aren’t many choices for a woman in your position, with no romantic prospects, so you take a job at your local tavern. It’s hard work but one day you come across a book that’s been left in a booth. Upon closer inspection you realise that the book in question is “Wuthering Heights”. Emily has always been kind of bitchy to you, but not in a way that when you describe it sounds like you aren’t being the unreasonable one. Do you keep the book and sell it as your own or do you return it to her?
    Is your date uncomfortable being a hypothetical woman (if they’re male) albeit however briefly? Are they the kind of person who would keep something clearly important if they found it, or would they turn it in like a responsible adult? 
  8. You have accepted a new job in an area you have neither heard of nor appears to have any online presence. This doesn’t put you off, and upon arrival you discover that your new neighbours are a coven of witches who also maybe work for Google. You want to take a present over to get off on the correct foot, and to avoid any potential hexings down the line if your dog digs up their impressive looking rose bushes. What do you take?
    Find out how good at giving gifts your date is off the bat. No disappointing holidays and birthdays for you. 
  9. As an international super assassin you have been around the block a few times. Your speciality is fake accents, and making a person disappear without a trace. It’s a Tuesday and you’re sipping your morning coffee when your newest hit comes in. It’s you. Apparently your spouse has decided murder is easier than divorce, and has accidentally hired your alter ego to kill you for the insurance payout. You did think it was a little odd when they upped it last month. They’re away on a business trip until Friday night – how do you make them pay?
    Off the bat find out if your potential spouse is not only creative, but if they are the kind of vindictive creative that could come back to haunt you if you do them dirty. Also a good way to find out how many crime novels they read. 
  10. So as it turns out Hades, god of the underworld, is real and is now sitting in your living room. After some tea followed by a surprisingly easy game of chinese checkers you have discovered that beating the god of death, regardless of your intention to just pass the time while your guest waited for your upstairs neighbour ‘Greg the smoker’ to return and fall down the stairs, means you can choose one of two things. You can either have him bring back a soul from the underworld, your choice of who, or you can be given immortality. What do you pick?
    This one gives your date the opportunity to open up about someone they have lost, or any easy out. Plus if they take the out, then find out what they’d do if time and danger were no longer an issue.

 

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