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Three Intriguing First Date Questions (That Ensure You’ll See Each Other Again)

August 17, 2018

3 Intriguing First Date Questions (That Ensure You’ll See Each Other Again)

In this article, you’re going to learn questions to ask on a first date that will actually engage the person intellectually, and more importantly, emotionally.

These questions will help you stand out from the sea of guys whose conversation goes as deep as a kiddie pool. Not only will they show your date that you’re interesting, they’ll also help you get to know what your date values in life – so you can decide if there’s potential for something real between the two of you.

First Date Question 1:

What would you do to survive if it was announced on the radio that a zombie virus is spreading rapidly?

This is a fun question that allows you and your date to make a story around a crazy scenario. You can tease her if she makes questionable decisions in her answer. For example, if she says, “I’d go find a gun in a store.”

You can tease her by responding, “You’d fight off the hordes of people scrambling to get weapons?”

You can challenge her answer (and she can challenge yours), making for an uncharacteristically playful conversation about the end of humanity.

This question will help keep your conversation engaging and emotional (as opposed to boring and logical).

First Date Question 2:

What’s more important to you, your personal happiness or achieving your goals?

One of the biggest mistakes people make in dating is only talking about surface-level, “safe” topics. Talking about your job or your favorite Netflix shows is fine, but if you want to make a connection with your date, at some point you want to go a bit deeper.

This question cuts right through the B.S. and gets you into a conversation about one of the big questions we all struggle with. This question can lead you into interesting topics like what makes your date happy, what they want to achieve in their life, and how they define the good life.

Not only can this question lead to an interesting philosophical discussion, but it can also help you understand whether you have any long-term compatibility with your date. If they value happiness over achievement, but you value achievement over happiness, that could become a source of stress in a long-term relationship between the two of you.

(PS: Follow me on Snapchat to see infield footage of me and my friends approaching women and bring girls home with us. Username = AveryGHayden)

First Date Question 3:

I’m going to tell you two truths and one lie; can you guess which is which?

This game is fun for its own sake, but it also can become an excuse to talk about interesting/funny stories about yourself. If one of your truths is that you once gave up a six-figure paying job to start an online business, you can bet she’s going to want to know the details of that story.

After you’ve played this game, you can switch roles and have your date tell two truths and one lie. This will give you the chance to learn some of her most interesting stories.

Play the Question Game:

The question game gives you and your date an excuse to talk about topics that would normally be taboo. To start, ask if she’d like to play the question game.

When she says yes, explain the rules, “There’s three rules to the question game: First, we ask each other questions back and forth. Second, we can’t ask the same question twice. Third, you’re allowed to pass if you don’t want to answer a particular question. The point is to ask questions you normally wouldn’t ask. Sound good?”

When I start the question game, I like to ask relatively innocuous questions (like the questions from earlier in this article), but I occasionally throw in something a bit more taboo (like the examples below).

If you get the sense your date doesn’t like answering questions with a sexual edge, don’t keep asking those kinds of questions. But if she has fun with it, keep going, it’s not only fun, but her answers can also give you insights as to how she wants to be kissed, what turns her on, etc.

You can ask anything you want in the question game. Part of the fun of the game is in its spontaneity, so I don’t recommend memorizing a list of questions before going on your date, but you can use the below list for some inspiration/ideas.

  1. Who is your celebrity crush? (but you can’t say Donald Trump)
  2. If you were a lesbian for a day, who would you hook up with?
  3. What was your first kiss like?
  4. What makes a kiss good in your opinion? (or bad)
  5. What about guys turns you on?


Wrapping up 3 Intriguing First Date Questions

At worst, a first date can feel like a job interview, at best it can feel like going on an adventure. Largely, it’s the quality of your conversations that will determine whether your dates are tolerable or exhilarating.

This article provided you with a number of interesting first date questions you can use to start conversations that are both fun and meaningful. Don’t limit yourself to only these questions – simply use them as a springboard to start talking about creative and emotional topics.

Once you’ve mastered that art of asking interesting questions, you can be confident that you’ll be able to lead your dates in whatever direction you want to, instead of feeling like you’re rolling the dice.


TheRedArchive is an archive of Red Pill content, including various subreddits and blogs. This post has been archived from the blog Red Pill Theory.

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Post Information
Title Three Intriguing First Date Questions (That Ensure You’ll See Each Other Again)
Author Avery
Date August 17, 2018 3:26 AM UTC (4 years ago)
Blog Red Pill Theory
Archive Link https://theredarchive.com/blog/Red-Pill-Theory/three-intriguing-first-date-questions-that-ensure.22649
Original Link https://redpilltheory.com/2018/08/17/three-intriguing-first-date-questions-that-ensure-youll-see-each-other-again/
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