5 Interesting Things to Say to a Woman You Just Met

The biggest problem men have when talking to the women they like is that they turn the conversation into a job interview. You hear this all the time and yet, it still happens, even when you have experience. The nerves never go away completely, and in their midst, you’re just looking for “interesting” things to say to reduce them. If you’re rusty, it’s prone to happen more.

While overcoming your anxiety around women is the most important part of getting better with them, that isn’t a straightforward process. It ebbs and flows with overall experience, recent experience, and know-how.

This post is intended mostly for guys just starting out, but the information should be useful no matter your level of experience. I’m always experimenting with new conversational threads. At this point, I’m more interested in testing different methods of persuasion than I am with any particular outcome with a woman.

The key thing is to avoid the dreaded, emotionless, boring job interview. You know what I mean. “What do you do? Why are you here?” Even if you do succeed in getting a phone number or an instant date, because she likes your look, or she appreciates your confidence, or she’s bored, she’s likely to flake. That’s the way of the world after the smartphone takeover. You need to make a physical and emotional connection to stand a better chance.

Instead of the job interview, here are 5 things to say to a woman that will make you more interesting and increase your chances of making a more powerful emotional connection. I’ve tested them and have had some success. You don’t need to say these things in order, though some are deeper than others.

1. Back to basics with Dale Carnegie

In How to Fail at Almost Everything and Still Win Big, Scott Adams relates what he learned in a Dale Carnegie public speaking class.

Your job as a conversationalist is to keep asking questions and keep looking for something you have in common with the stranger or something that interests you enough to wade into the topic. In my entire life, I have never met a stranger who didn’t have some fascinating life experiences that spilled out if I asked the right questions. Everyone is interesting if you make the situation feel safe.

The point of conversation is to make the other person feel good. If you do that one thing correctly, the other benefits come along with the deal. For example, a person who likes you is more likely to be persuaded, to recommend you for good opportunities, to share information, and to want a relationship with you.

On the surface, this sounds like the boring job interview, but the object is to get into deeper subjects by asking the right questions. Crucially, you need to let the other person talk and not dominate the conversation. That would be the anti-seductive trait that Robert Greene calls “the windbag” in The Art of Seduction. It’s the biggest mistake most people make, especially if your tendency is to dominate your social interactions like me. That’s the job interview.

The things you say to a woman you first meet should be about opening her up more deeply and trying to relate it back to yourself with something interesting. You need to be an active listener, not a talker.

2. Pose a riddle

After you’ve made your introduction and connected in some way to the woman you fancy, the first, amateur instinct is again, to say things that sound like a job interview. That’s what you want to avoid. Instead, after a minute or two, once you’ve had time to make a good first impression with your listening skills, confidence, and hopefully your look, say that you’ve rarely met someone that can answer this riddle on the first try. That might sound strange in writing, but in the ebb and flow of normal conversation, you can easily steer things there.

I picked this up after re-watching Are You Afraid of the Dark? for the Outskirts Battledome a couple of years ago. In the very first episode, the antagonist poses a riddle:

  1. It’s weightless.
  2. You can see it with the naked eye.
  3. If you put it in a barrel, it would make the barrel lighter.

Can you guess what it is? Comment on Disqus below!

The thing about this is that it’s fun, light, and engages the brain. In an age where smartphones encourage attention spans of less than 30 seconds, capturing that attention early is vital, and people love mysteries. It’s why top copywriters use them a lot in their sales letters.

Once you say the riddle, you can joke around and mislead her, and so on. The important thing is that she’s engaged instead of simply being polite, and you’re having fun together.

This doesn’t work all the time, but it works enough.

Speed and Trixie

3. Use simple hypnosis

If you aren’t blown off immediately by the woman you just met, you’ll have opportunities to say interesting things about yourself. I often say things related to social psychology and persuasion, and what I do with them. Talking about people and not about things is usually a better approach. In these conversations, I get the woman to play along with a little hypnosis game that I learned from a comment on Scott Adams’ blog.

  1. Tell her to spell out the word S-H-O-P three times fast.
  2. Ask her what you she does at a GREEN light?

A lot of times, she’ll say “stop.” Then you can tease her about stopping at a green light.

This formula doesn’t always work, but it works much of the time. Your delivery matters a lot. You need to get her to spell out the word quickly and efficiently, and then ask the question without any hesitation, if you want to get the best results.

If it works, it’s an interesting demonstration of the power of hypnosis and attention channeling, and since it’s about how the human brain works and socializes, the woman will likely be into it. Once again, her brain will be engaged. At the very least, you’ll be interesting and unique, as no other men will say this kind of stuff to her.

Sure, it’s being a clown to some extent, but you’re the man, so it’s your responsibility to turn on the charm. Males charm, females select. That’s just the way things work in the animal kingdom. Adapt or die.

4. Funny tweet readings

The thing about laughter is that it’s contagious. Even if you aren’t the kind of guy that can make a woman laugh on command, you can use material that makes you laugh, and she’ll probably join you naturally. I was inspired to test this out by Quintus Curtius’ G Manifesto tweet reading podcasts. Hearing him laugh hysterically made me laugh, too.

Recently, I’ve put my smartphone to good use, giving me more things to say to a woman I just met. I’ve been reading some of the G Manifesto’s tweets and laughing hysterically. The content doesn’t matter. The emotions do. G Manifesto is one of the great social parodists of our time, so feel free to use him in your conversations. It’s just so otherworldly and surreal that you can’t not laugh.

Sharing hysterical bouts of laughter will create a more powerful social bond with a woman than most of what you say. That’s why humor evolved.

Gerald and Phoebe

5. Exchange more and more personal questions

In Pre-Suasion, Robert Cialdini highlights an exercise that, when used, has led to much more intimate relationships between the people involved in them, and even some marriages. The idea behind it is that you will ask each other and then answer a series of 36 questions that incline in importance. You start slow, with a question like “what would be a perfect day for you?”

Later on, you would say something like “what do you value most in a friendship?”

Near the end, you’d ask “of anyone in your family, whose death would be most disturbing?”

The mutual reciprocation of increasingly personal information blurs the self/other distinction and cements this unity because you and the woman you fancy will be acting together. I’ll let you read Pre-Suasion for more on the psychological mechanisms behind this, but for now, just know that this is one of the most interesting and powerful tools you have to break the ice.

Until then, read Stumped for more interesting things to say (the persuasion angle about Trump has intrigued the women I’ve met, even the ones who hate Trump).

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