How To Have An Engaging Conversation With The Girl Of Your Dreams

Asking questions is a great way to get to know that girl you like a bit better, but it depends on the kind of questions you’re asking. The last thing you want to do is make it feel like an interrogation. You shouldn’t be asking anyone serial questions over the course of one encounter.

Instead, you should be having a conversation, sharing a bit about you and then getting a bit back from them. So how do you ask the questions that lead to deep, fulfilling conversations?

Asking the right questions is a great way of getting to know a girl you may want to start dating

Don’t Think About Questions – Be In The Moment

Girls love to talk about themselves, so all you have to do is keep peppering her with questions and she’ll be putty in your hands, right?


Random questions asked for the sake of asking them will impress no one. Demonstrate good listening skills by being genuinely interested

You shouldn’t ask questions just to ask them — you should be asking because you’re genuinely interested in what she has to say.

If your conversation is a car, then questions are the gasoline: they keep things moving, but if you use too much, the whole thing will stall.

You need to be present in the conversation, which is next to impossible if you’re too busy thinking of the next question. Don’t fixate on what you want to ask her; instead, just focus on general topics of discussion and let the conversation build from there.

Ask The Questions, Then Listen To Her Answers

The simplest way to keep a conversation moving smoothly isn’t by always keeping an endless stockpile of general questions in your back pocket. Why? Because conversations work best without a structure.

“Be the in moment, laugh when it’s funny and be curious”

That doesn’t mean you should just blurt out whatever pops into your head (Rugs! Baby powder! A fern! Sun burning out?!) — when I say “without a structure,” I mean the conversation should naturally go wherever it happens to go. But to do that effectively, you need to know how to listen.

Charm your dates with naturally flowing conversations. This starts by not stockpiling generic questions

Depending on who you ask, there are a variety of different styles of listening. [R]

Types of listening
Source: Changing Minds

For our purposes, there are four main ones that people employ in conversation, particularly in a dating environment with someone you are getting to know:

  • Pseudo-listening — Pretending to listen without actually paying attention
  • Ambient listening — Listening, but your attention isn’t fully focused
  • Dialogue listening — Listening to what she’s saying, but not how she’s saying it
  • Empathic listening — Fully engaged, paying attention to the verbal and non-verbal cues

Empathic listening is by far the best listening style — not only are you fully paying attention to what she’s saying, you’re also responding to her tone, her body language, and her emotional state.

Here’s how each listening style plays out in practice.
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Empathic listening takes the most effort, but it also leads to a far more robust conversation.

Be Enthusiastic

Conversations are like bank accounts: you get out of them what you put into them. (Unless you…get hit with overdraft fees. Look, just go with it.)

A great conversation hinges on enthusiasm. Even the most boring subject can be made more fun and interesting if you approach it confidently. Enthusiasm is contagious; studies have shown that people respond to enthusiasm [R], so if she sees that you’re having fun talking about your favorite accounting methods, she’ll have fun joining in. To see how you can make any topic entertaining, watch Tyler’s talk on free-styling, intonation and making boring topics fun.

Enthusiasm is also crucial when asking questions — you should be excited to hear her answers, because those answers are telling you more and more about her as a person. And if she feels like you’re excited to learn about her, she’ll be more willing to open up to you.

Put Your Body To Work

Not like that. (Although, if you do it right, you won’t have long to wait.) I’m talking about body language, which is a great non-verbal way to express your interest in a girl. [R]

Sometimes more can be said without the use of words

Eye contact is a great place to start. Whether you’re talking or listening, meet her gaze. It shows that you’re engaged and invested in the conversation.

Source: SAGE Journals

The following experiment demonstrates the importance of eye contact and facial expressions. A person randomly selected 280 people and made one of three gestures – a) Looking through them with no eye contact, b) Acknowledge them with eye contact, or c) Acknowledge them with eye contact and a smile.

The data shows that the people who got no eye contact felt the most disconnected. The people who had the eye contact with the smile felt the most connected… so what should this be telling us to do when we are on our dates?

Oh and not to sound like a TV mom from the 1950s, but when you’re talking to her, sit up straight! Don’t slump in your chair or put your hands behind your head. You might think these positions make you look cool, but in reality, you’re coming off as disinterested and aloof. It’s not enough to be mentally present in the conversation; you also have to be physically present.

Don’t Ask Simple Questions (Or You’ll Get Simple Answers)

The whole point of asking questions is to get to know her better, but if you ask straightforward questions, you’re going to get straightforward answers that barely scratch the surface. Plus, asking questions that can be answered with a “yes” or “no” doesn’t leave you any room to build on them, which means lots of awkward silences while you rack your brains for another thing to ask her.

Simple straightforward questions do not spark meaningful conversations

If questions are the gasoline of the conversational engine, yes or no questions are like a mixture of gas and water: using them to drive the conversation will only cause it to sputter.

So how do you ask the kind of questions that will spark a meaningful conversation?

Use The Past/Present/Future Method

In a nutshell, the “Past/Present/Future” method combines a statement about your past, present or future with a related question about her. Using this method helps you learn about her while also opening up about yourself.

Here are some examples:

Past Questions

“When I was a kid, I wanted to be Michael Jordan. Not like Michael Jordan — I wanted to be the actual Michael Jordan. What did you want to be?”

“I tried this great Thai restaurant downtown with a really unique menu last month and I’ve been dying to go back. You hungry?” OR: “I’m looking for new go-to places like that…”

Present Questions

“I spent the afternoon building some stuff for my apartment — I really enjoy working with my hands. You?”

“I just watched ‘Moonlight’ for the first time and I’ll admit, some of the scenes got me a little misty. I mean… uhhh, I don’t cry at movies, do you?”

Future Questions

“I really want to take a vacation to Vanuatu, this remote island in the Pacific. You?”

“By the time I’m 40, I’d like to have my own business buying alcohol and selling it to teenage kids at an insane markup. What’s your masterplan?”

Remember, conversations can still be fun, cute and flirty while deep without getting personal

The key to a meaningful conversation is to not set expectations for the conversation before it starts. Follow these tips, and a seamless, deep conversation with the girl of your dreams will be a walk in the park.

And remember, try to have fun, flirt a little and have laugh…. make it a great day out.

Resources & References

Still unsure or nervous about communicating with a girl? Then these sources and references may be of interest.

  1. Well done if you plucked up the courage to chat to the woman of your dreams. The next stage is making your dream woman obsess over you, and here’s exactly how thanks to The Social Man
  2. 84 questions to ask on a first date – Huffington Post by Alexis Meads
  3. 7 questions you should ask on a first date by ThinkTank
  4. An interesting list on the many types of listening by Changing Minds
  5. Enthusiasm and positive personal impact – Fast Company by Bud Bilanich
  6. What to talk about on a first date (and what not to talk about) by Tripp Advice
  7. Your body language by Improve Your Social Skills