Questions to ask on a date

Got any good ones? Here are some of mine: (to be asked in moderation — not meant to be used as a questionaire or interview! but especially good for online dating.)

Is there something you’ve dreamed of doing for a long time? What prevents you from doing it?

If you knew that in one year you would die suddenly, would you change anything about the way you are now living? If so, what?

If you could take a one month trip anywhere in the world and money was not a consideration, where would you go? What would you do there?

If you had one day in your life to live over, which would you choose and why?

What do you think is the single best decision you’ve made in your life so far?

Name one thing you could do to improve any important relationship in your life.

If you could change anything about the way you were raised, what would it be?

What is your most treasured memory?

What was the most risky decision you ever made in your life? What made the risk so great?

What was the high point of last month?

What is the one thing about yourself you like best?

What is the worst psychological torture you can imagine suffering?

What, if anything, is too serious to be joked about?

If you were guaranteed honest responses to any three questions, whom would you question, and what would you ask?

What do you value most in a relationship?

If you were to wake up tomorrow morning to learn that the headlines of all the major newspapers were about you, what would you want them to say?

Lance Default Asked on January 28, 2020 in Love & Relationships.
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6 Answer(s)

I wish I met a girl asking me exactly these kinds of questions (because I’m prepared ).

Here’s another one (needs rephrasing because it sounds overly serious): Is there a general life strategy/rule of thumb you follow/live by?

Base Default Answered on February 1, 2020.
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I’d list some of mine, but I don’t ask any questions during dates (apart from ‘what would you like to drink’). I just talk about whatever springs to mind and be sure to leave plenty of room for you to talk as well.

I find that just talking leads to much more interesting conversations than asking questions does.

We’ll likely end up with a fairly balanced dialogue if you are the least bit interesting. If the night turned into a monologue about me, don’t expect me to call you again.

(Theoretically, the night could also have turned into a monologue about you – but that has never happened to me yet)

Archibald Trainee Answered on February 10, 2020.
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I am going to ask myself those questions! I think they’d probably get you a better picture of someone than the old standby “what kind of music do you like?” Even if John Cusack and his buddies decided what you like matters more than what you are like.

It’s amazing that we don’t ask ourselves these types of questions (well, at least I haven’t). I think I could learn a lot about myself by doing so.

admin Professor Answered on February 13, 2020.
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I think it’s very important to ask thoughtful questions on a date, and to have a couple in mind to ask — it shows you’re interested in finding out who she really is, that you’re a leader, that you are entertaining (of course there is nothing more entertaining that being asked about yourself, right?). It’s great to be prepared with a question that will spark fire into a conversation and get it really rolling.

Give one or two of these a try — see how much fun it is to watch your date’s face as she considers her answer.

Arch Default Answered on February 19, 2020.
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Absolutely! They’re very interesting questions of course. I’m going to ask that myself too…

I’m lucky that you warned me about american dates before I could date an american. Imagine the catastrophe without that…

If I’m allowed to be rude ( ), I guess I would send him some red-flag-detector-missiles first, and then come up with interesting questions.

Antonius Default Answered on March 12, 2020.
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One more question designed especially for you:

“Do I have spinach caught in my teeth?

Boony Default Answered on April 11, 2020.
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