Your First Date is a Reconnaissance Mission. Here's Your Strategy.

Forget about romance, chemistry, and vibe . . . for now.

This piece was inspired by a Burned Haystack community member’s question:

“I'm watching Love is Blind and just wondering what questions you would ask on the first date to elicit information best? The same ones you ask on app conversations?”

My answer to this question ties directly to a mindset-shift orientation I address in depth in my book (link to pre-order here), but briefly: In the early stages of dating, you need to be in “business/social scientist” mode, NOT romance mode. If you handle the former effectively, the latter will be WAY better. That was an over-simplified overview, but it’ll suffice for now.

Here is my response to the question:

I think the trick here is to make it conversational rather than interrogational and to not lead the witness.

For example, I would *not* ask someone something like, “What’s your stance on reproductive freedom?” or “Did you vote for Trump?” Instead, I ask questions like the ones below (I employ some of these in my profile sometimes, too, and I don’t duplicate, so these are questions I’d ask on a date if they hadn’t come up in my profile or in previous messaging):

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• Refer to some kind of weather disaster or war in another country or increasing AI usage to lead into this and then say something like this: “Doesn’t everything feel, like . . . apocalyptic right now??? 😬”
  
  Questions like this tend to bring out people’s political orientation in an instant without them having any idea of what’s happening. The conservative dudes or the “apolitical” crowd will either simply not care, or they’ll discount it as “liberal snowflake stuff” or if they’re totally unhinged they’ll start talking about Satan or the breakdown of the traditional American family or how we need more guns or whatever.
  
  You never know how it'll come out, but in my experience it almost ALWAYS comes out quick.
  
  

• Say something about Gen Z and how different they are – how they talk differently, seem to have different value systems, use all different pronouns for each other, etc. Your goal here is to see if men respond with good-natured tolerance for youth. If they start railing against an entire generation or seem hostile, that’s a bad sign.
  
  

• Mention Taylor and Travis’ engagement 😂 (or the Barbie movie, or whatever the “cultural thing” of the moment is). Uber conservative and toxic men hate Taylor Swift. It doesn’t even matter whether you like her music; an adult man being threatened by Taylor Swift is a big red flag because she’s emblematic of successful feminism. An outsized or overly angry reaction here is a problem.
  
  

• Think of some angle that’s relevant to you or your job that can get at deep topics without it seeming like that’s what you’re doing. For me, I mention that I taught in a prison for a while. It was a men’s max-security prison with a horrible record of human rights violations and environmental hazards and it’s in the news a lot here, so people know about it. I bring this up because I want to see if men can have any kind of nuance or empathy or understanding of the complexity of things like systemic racism and violence in the criminal justice system or if they’re just going to be like, “Welp, I guess they’re getting what they deserve” or worse (I’ve heard way worse responses to this).
  
  Depending upon what you do, you could refer to medical access issues or education issues or economic issues or labor inequity issues or labor conditions issues --- all of these things intersect with both politics and the capacity for humanity.

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The general rule for these kind of questions is this:

“complex topic + space to expand and expound”

This is how you get meaningful information from people. And then you just let them go and you listen closely.

It’s also important here to make the thought-shift between going out on a date hoping they’ll like you and going out on a date to figure out whether you will like them. Stay in the latter mode.

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I want to close this piece by heading off a potential critique of everything I’ve just written, which sounds like this:

“Why are you encouraging women to be so cagey? It’s 2025, we’re allowed to be direct and not beat around the bush. I don’t have time for this.”

I get that. But firing off a bunch of obviously hot-button questions on an early date is, number one, sort of socially tone deaf (says someone who’s done exactly that in the past 😂), and number two: not a fraction as effective.

If you want an authentic picture of who you’re sitting across from, the questions (or equivalent) that I’ve outlined in this piece will give you a much richer, more layered, and more accurate concept of someone, and it’ll prevent them from lying to or manipulating you. Will it work with genius psychopaths? No, but nothing does, and that’s a very small percentage of humans anyway. This will work with most men.

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Asking readers to share their own questions /ideas / strategies now . . .