15 Great Hypothetical Conversation Starters for 2019

hypothetical questions

If you meet new people often, you know that small talk can get terribly boring. You have probably realized by now that typical small talk is made up of a limited number of seemingly prescripted questions. The same old dreary questions will yield the same old dull answers. Even if you have upped your small talk game from the weather to something less common, it could still be a difficult task to keep the conversation going, especially if the person you are talking to gives one-word answers.

You most likely want to get to know someone immediately when the conversation begins and would prefer to get away from the same old boring questions. Feel free to throw ‘norm’ out the window and ask out-of-the-ordinary questions. You can be sure that they will give you out-of-the-ordinary, fun answers that will help you get to know the person quite quickly – and at a more profound level too.

Here is a list of fun hypothetical questions which need no introduction. You can dive right into them so you can use them as ice-breakers too. As you ask these questions, be prepared to have some people think of you as strange but that would only be a problem if you are bothered by what people think about you. Besides, isn’t it much better to be thought of as a weirdo than a plain Jane that nobody will remember? At least you will definitely leave an impression! 😛

Hypothetical Questions To Ask

1. Anonymous Killer

An extremely close friend who you have known almost all your life is suffering from a terrible disease. He or she is paralyzed and is in immense pain. You know the disease will make them waste away gradually and eventually die in about a month. In desperate pain and frustration, they secretly beg you to give them a single, painless injection that will kill them instantly. Your friend assured you that no one will ever know of the deal. Would you give them the injection?

2. Extra-Terrestrial Experience

You are taking a run in a field and a strange looking craft crash lands a few meters away from you. You can’t help but walk up to it just to see what it is. After the smoke clears away, you see the bodies of two small extra-terrestrial creatures. They are alive but look weak. No one else has seen the craft or the creatures. Would you take them home with you? Would you call the authorities? Would you walk away and pretend you never saw anything?

What would you do?

3. Do You Want To Be ‘Stinking’ But Rich?

You have been dared to spend three months without ever taking a shower, brushing your teeth, or using deodorant – in exchange for $35,000! You must not say anything to anyone about the deal for the three months and go about your daily life as usual. Would you take the dare?

4. Freeze or Die?

You have an incurable disease and as a result of that, you know without a doubt that you will die in just three months. You have the option to die and be buried like everyone else or be cryogenically frozen. This would essentially preserve you for hundreds of years, after which, technology could advance to potentially have a cure for the disease and you can have a chance for a longer life. Which one would you choose?

5. Short-lived Perfection

Every girl dreams of one day meeting the man of her dreams – her one true love. Now you have a choice between two paths. On the first one, you meet this perfect man and spend six of the most amazing months of your life with him. As you make the choice, you know that he will cheat on you after six months and immediately leave you for another woman, wanting to have absolutely nothing to do with you while shattering your heart into a million pieces. If you opt for this option, you would go into it without the knowledge of what will happen later. On the second path, you would never meet him at all. Which option would you take? Would you like to meet him and enjoy a phenomenally blissful six months and bear the pain later or skip the entire experience altogether? Is it better to have loved and lost or never to have loved at all?

6. Lottery Winner

You have just won $10,000 in the lottery. You have two options, to keep all the money for yourself or share it equally among 100 strangers. You have no idea who the 100 people are but you are sure that they really need the $100 and would truly appreciate it. Would you share or keep it all?

7. Alternate Sex

You have just learned of an alternate universe with the exact alternates of every individual in this current world we are living in. You have located your alternate who happens to be of the opposite sex. There are barely any differences between you, except for your gender. Would you have sex with your alternate self?

8. ‘I do’ or ‘I don’t’

It is two weeks to your wedding day and you are super excited about it. You can’t wait to spend the rest of your life with the love of your life. Unfortunately, your fiancé gets into an accident which leaves him paraplegic. Would you still get married or call off the wedding?

9. Haunted House Dare

Picture an old, abandoned house in a remote part of the countryside which is many miles away from any form of civilization. If you have never seen one in real life, you must have seen one in a movie. Your friends have dared you to spend a night in a house like this. It would be no big deal but the house is believed to be haunted and there is no electricity but clean running water is available. The nearest neighbors live eight miles away so you are pretty much on your own. The only thing you are allowed to bring is a flashlight. Would you accept the dare?

10. Russian Roulette

Have you ever played Russian Roulette before? What if you had a similar kind of game? You have in front of you $1,000,000 on one side of the table and on the other is a set of ten pistols. Only one of the ten is loaded. You are required to pick any one of the guns, put it to your head and pull the trigger. If the gun is not loaded and you are unharmed, you get to keep the money. Would you take the risk?

11. Good Vs. Evil

Insomnia seems to have gotten the best of you yet again. It is the middle of the night, you are sitting in your dimly lit living room when you suddenly hear the voice of God. He speaks to you telling you that the war against Satan has finally been won. Now he wants to take you to heaven but he cannot do that unless he removes from you the knowledge of good and evil. You must bear the complete innocence of a child to be able to get into his kingdom.

Immediately after that, God disappears and Satan appears with a counter message. “Get away from Him!” he says. “I have spent all these years making sure that you get to know the truth about good and evil so you could create your own path, in your own way. You can’t let all that effort go to waste now.”

He tells you to join him in another world which he has created. In this world, you will get to live your life much like your life in this world. In it, you will live a full life and die like normal. What would you do? Who would you believe?

12. Transgendered Perfection

You have finally met the woman of your dreams. The woman you always knew could only exist in your mind because she is perfect. She is dazzlingly beautiful, she is smart, and has the most beautiful personality. You can feel yourself falling in love with her more and more every day as you get to know each other better and it is obvious that she feels the same way too – it is all just utter perfection. The only problem is that it seems like there is something holding her back from taking the relationship any further. After more than a little probing from you, she finally tells you that there is something she has to tell you before you take the next step. She confesses that she is transgendered and still has a penis but intends to correct this in the very near future. What would you do? Would you break up with her? Would you wait for her to have the corrective surgery and proceed with the relationship? Would you take a break from the relationship until it is done?

13. Baby Mix-up

Exactly one year ago, you brought home your bundle of joy with overflowing love for the adorable little person. He has grown into a brilliant little guy who adores his mommy. The hospital just informed you that there was a ‘slight’ mix up and the child is actually not yours. Your biological child is with another family and you should exchange children to correct the mistake. What would you do? Would you agree to exchange the child? Would you openly refuse to do the exchange? Would you run away with the child and make sure they never find you?

14. Life Saver Dilemma

Imagine you are leading a delicate rescue mission in which 100 people are to be rescued. All their lives are at risk and you have only two options. The first option will certainly kill 10 people but the rest will definitely live. The second option gives you a 70% chance of saving all 100 people but in the event that it fails, all the 100 people will die. You have only a minute to make a decision. Which option would you choose?

15. Your Whole Life Is a Computer Simulation

What if you discover that life and the world as you know it is actually a simulation run by one big machine? All your childhood memories, your friends, family, work … everything is part of a program. You actually do not have a body, you are a brain running on a computer program used to simulate every aspect of your life. No one outside the simulation knows that you have learned the secret so you have to go about your life as normal and pretend you do not know the truth. What would you do? Would you try to escape or would you tell everyone else?

Bottom Line

Answering hypothetical questions and scenarios are fun ways to get to know someone. You can easily get a feel of who a person really is through this kind of questions, especially if you catch them off guard. You can get to know a person not only by the answers they give but also by their willingness to play the game and how they play it. Go ahead and try a few. You are bound to get some pretty outrageous answers and a guaranteed fun time!

More: 70 Awkward Questions to Make a Guy Cringe


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