Questions to Ask a Guy: The Rapid Intimacy ToolMaybe there’s a guy you have a crush on.

And maybe you’d like to move past awkward small talk with him so he can realize what an interesting person you are.

In that case, it would be helpful to know the right questions to ask a guy. Questions that make him slip effortlessly into deeper conversations with you.

I’m talking about the kind of conversations that can last for hours while only feeling like a few minutes, leaving you both wishing for more, reluctant to be pulled away.

If that’s you, you’ve come to the right place.

Because I’m about to show you some of the best conversation techniques I’ve ever found.

These are techniques I teach my private clients as a dating and relationship coach. And I’ve never shared them publicly until now.

Ready to get started? Then let’s begin with a trigger for deep, soulful conversations.

The Intimacy Trigger that Works Every Time

If you want a guy to stay up talking all night, Dr. Arthur Aron has some suggestions.

In a now-classic study,[1] Dr. Aron and his colleagues wanted to see if they could create a close relationship in the laboratory…

Between two complete strangers.

Their test succeeded beyond their wildest dreams.

They only intended to see if they could get two strangers to feel close to each other—they had no intention of causing anyone to fall in love.

When they originally tested their procedure, they matched opposite-sex partners in a comfortable room and handed them a series of questions to ask each other. It was just a single session of talking.

When the researchers followed up with participants several months later, they found many of these pairs had built a real-world connection with each other—and one couple eventually got married!

What was the trick to getting these pairs of strangers to bond so fast and so deeply?

In the words of the study itself, all it took was:

“Sustained, escalating, reciprocal, personalistic self-disclosure.”

Or, put simply, revealing more and more about yourself while your partner does the same.

After using the technique I’m about to share with you, 30% of participants felt closer to a stranger after just 45 minutes…

…Than they did to the closest person in their lives.

Imagine the power of this technique. In under an hour it can build a feeling of intimacy that rivals your strongest bond.


By getting you both to gradually open up through a series of tiny increments toward intimate self-disclosure.

Now, in just a minute I’m going to show you some questions to ask a guy so you can trigger this same amazing bonding reaction. But first, let me explain a bit more about how the research team did it.

How Scientists Created Romance Out of Thin Air

Here’s how it worked.

Dr. Aron put his paired-off participants in a room alone together, with no other distractions, for 45 minutes. Having that level of privacy helped participants feel safe opening up.

He then asked them to each answer a series of 36 questions, broken into 3 sets.

The first set of questions is typical first date fare: what’s your life story, would you like to be famous, what are you most grateful for.

Those questions were really just ice-breakers to get the conversation flowing. But still pulling gently for self-disclosure.

After 15 minutes—regardless of whether they’d finished all the questions or not—participants switched to a deeper set of questions. These questions focused on hopes and dreams, memories, values, and family relationships.

Fifteen minutes later, participants switched to the final set of questions.

These questions were challenging. They asked participants to share moments that might normally be difficult to talk about: embarrassments, regrets, and loss.

Even more crucially, participants were asked to share their honest thoughts and feelings about each other. That takes guts…so you have to gradually work up to a question like that.

The key is just to remember one simple thing. Gradual escalation of self-disclosure. In other words, opening up about things you typically wouldn’t tell a stranger.

If you’d like, you can scroll down to the bottom of this article to read the sequence of questions that led to such powerful results.

Do you want to put this concept to use?

Then let me show you how.

You see, there’s a tendency to avoid deep questions when we first meet people. But that’s a mistake.

Rote questions like “How are you,” and “What do you do?” fizzle out quickly, because they lack the curiosity, wonder, and genuine interest that makes a conversation come to life.

You can do better than that. I teach my clients to use profound questions right from the start, even with strangers.

One of my favorite low-stress starter questions is “What made you laugh today?”

Here are a few more questions you could ask a guy to trigger the self-disclosure effect.

What problem do you wish you could solve?

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

What did you want to be when you were growing up?

What would constitute a perfect day for you?

When did you last cry in front of another person, or alone?

Triggering self-disclosure is powerful. But it works even better if it emerges naturally in the form of a story. So let’s talk about that next.

Ask For A Story

Stories lead naturally to self-disclosure. But how do you get a guy to launch into a story about his life?

In their book What to Talk About, Colin and Baedeker point out that stories can be prompted by the use of good questions.

Instead of this:

You: “When did you move to Chicago?”

Him: “Six years ago.”

You: “Do you like it here?”

Him: “Yes.”

Use questions that naturally pull for a story. Like this:

“What was it like when you first moved to Chicago?”

“What’s the weirdest thing that’s happened to you since you moved here?”

These questions pull for a story. And that story will get him opening up to you (self-disclosure) in ways the typical rote questions never do.

Okay, quick review. Here’s what you’ve learned so far:

Step 1: Go straight for deep questions.

Step 2: Ask questions that naturally pull for a story.

And now we are going to add a third step…

Step 3: Make sure he “feels felt.”

When people feel felt, they like you more.

The key is listening in a way that causes you to imagine what they must be feeling. This evokes your natural empathy, causing your body language to change.

Your way of being with them shifts toward a deeper level of listening that has become rare in our modern world of distractions.

On the verbal level, you can help him to feel felt by asking directly about emotions he might have been experiencing as he relays a story about a recent experience. For example …

“As I imagine myself in your shoes I feel a lot of frustration. Is that how it felt?”

This is the perfect kind of question to ask a guy. It’s not a specific question you can memorize, but it’s a formula you can use over and over again.

You just get him talking about something. Then imagine yourself in his shoes. Then ask about the emotion guys tend to leave out of their stories. He’ll feel felt, and that will do wonders to build intimacy fast.

Now, here’s the real magic of helping people to feel felt. When you mirror what someone feels, it causes them to mirror you back automatically, because of something called “mirror neurons” in our brain.

Mirror neurons will cause him to become attuned to you without even trying. But it only works if he feels felt.

We humans are wired to mirror those who are emotionally tuned into us. It’s an irresistible impulse that pulls people closer together.

Now that you have a formula for coming up with questions to ask a guy, you might want to learn…

Something Even More Powerful

Because deep conversations are great. But you need to take the next step if you want to sweep a man off his feet.

If you decide you’d like to take things to the next level, you won’t want to miss this video where I reveal a secret far more powerful than asking the right questions.

It reveals a secret obsession hidden in the heart of every man you know. An obsession so strong, you can trigger his love and devotion just by dipping your toe into this powerful pool of untapped potential for romantic bliss.

If you’d like to see what I’m talking about, and how you can start using it the next time you see your guy, watch this video now.

Dr. Arthur Aron’s 36 Questions[1]

Set I

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?
  2. Would you like to be famous? In what way?
  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
  4. What would constitute a “perfect” day for you?
  5. When did you last sing to yourself? To someone else?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  7. Do you have a secret hunch about how you will die?
  8. Name three things you and your partner appear to have in common.
  9. For what in your life do you feel most grateful?
  10. If you could change anything about the way you were raised, what would it be?
  11. Take four minutes and tell your partner your life story in as much detail as possible.
  12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

Set II

  1. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
  2. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  3. What is the greatest accomplishment of your life?
  4. What do you value most in a friendship?
  5. What is your most treasured memory?
  6. What is your most terrible memory?
  7. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  8. What does friendship mean to you?
  9. What roles do love and affection play in your life?
  10. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
  11. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  12. How do you feel about your relationship with your mother?


  1. Make three true “we” statements each. For instance, “We are both in this room feeling …”
  2. Complete this sentence: “I wish I had someone with whom I could share …”
  3. Original: If you were going to become a close friend with your partner, please share what would be important for him or her to know.
    Modified: If you were to stay together for the next 50 years with your partner, please share what would be important for him or her to know.
  4. Original: Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
    Modified: Tell your partner what you like about them; be very honest this time, saying things that you haven’t told your partner before.
  5. Share with your partner an embarrassing moment in your life.
  6. When did you last cry in front of another person? By yourself?
  7. Original: Tell your partner something that you like about them already.
    Modified: Tell your partner the first thing you noticed about them. What went through your head when you met for the first time?
  8. What, if anything, is too serious to be joked about?
  9. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  10. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  11. Of all the people in your family, whose death would you find most disturbing? Why?
  12. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

Questions for a Guy Who Doesn’t Talk about Feelings

What if your guy doesn’t respond to deep questions?

Well, if that’s the situation you find yourself in, this next bit is for you.

The truth is, some guys find it difficult to talk about emotions.

The very conversations that would pull you towards intimacy are the ones he avoids!

That can be frustrating to say the least.

Even if he did know what to say, he finds emotions embarrassing. He’s on solid ground when it comes to weekend plans and sports teams. But all that mushy stuff? It’s for girls.

But YOU know feelings matter.

You know he’ll feel better if he just opens up and shares what’s going on for him.

And here’s something interesting. Men have better mental health when they make time to talk.

Being a “real man” has a price. Strong, silent types can feel isolated and distant from those they love. To be truly known by another, you have to open up.

So how can you help him do that? AND get the heart-to-heart you’ve been yearning for in the process?

How To Make This Work in Your Relationship

It’s tempting to think you can get him to open up by asking him the perfect question or asking about topics he’s naturally interested in.

But springing a deep, philosophical question on this type of guy is sure to make him clam up.

And asking him about sports or gadgets may get him talking, but it’s not likely to lead to deeper emotional intimacy.

In just a minute I’m going to give you 4 questions you can ask your boyfriend every single day. These questions address topics that never go out of style and always lead to a more intimate relationship.

But first, let me show you how to pave the way to better conversations with him.

Whether it’s cultural or biological, women are usually considered better at talking than men.

He knows you love to talk. He knows you’re good at it. And in general he lets you do the thing you’re good at. You talk; he listens (or pretends to).

Getting him to talk more starts with reversing those roles.

Step back. You’re the quiet one this time. Try not to jump in with your thoughts and ideas. Give him time to think, even if it means uncomfortable stretches of silence.

Some men feel that their partners don’t want to hear what they have to say. That their partners are just waiting to get a word in edgewise.

Work on encouraging him rather than giving him feedback or your own opinion. You may find the less you say, the more he feels heard. You might even thank him for sharing his thoughts with you. Your appreciation will encourage him to do it again.

With those tips in mind, we need to tackle the question…

What Topics Will Get Him Talking?

There are 4 things you can talk about every day without fail. Make it a habit, and you’ll be amazed at how much closer and connected you feel.

The best way to make anything a habit is to schedule it into your daily routine. Set aside time when you get home from work, over dinner, or when you’re lying in bed at night. You’ll need at least 20 minutes.

Take turns sharing:

  • What went wrong
  • What went right
  • What you’re grateful for
  • What you wish for

Here’s why these questions are so powerful.

What went wrong. Knowing you’ve got someone to come home and complain to makes getting through a difficult day so much easier. So let your partner vent.

What went right. Couples who celebrate each other’s small wins stay together. Never fear that praising your guy will go to his head. It’s your job to be each other’s biggest fan.

What you’re grateful for. This is a chance to go a little deeper. Maybe you’re grateful the warm weather is holding out, or maybe you’re grateful for the love you share.

What you wish for. End the conversation with a positive hope for the future. This is a chance to support each other’s goals.

So what are you waiting for? Ask your man these questions tonight.

And see if he’ll join you in making these heart-to-hearts a habit.

P.S. Still reading? Then maybe you’d like to learn the conversation topics men always enjoy.

I’ve created a mini-report that gives you the best topics he’ll never get bored with. Just follow this link to check it out now, and I’ll see you on the other side!


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