Easy Ways To Have Deep Conversations And Get Guys To Open Up To You

Stephen Hussey

“Constantly talking isn’t necessarily communicating.” – Joel, Eternal Sunshine of the Spotless Mind

Every relationship begins with a conversation.

Every friendship is defined by a long string of experiences and conversations about those experiences.

Even every bout of meaningless, passionate, wild sex is punctuated by the odd dialogue about who you both are and what you are doing in the universe.

Conversation never stops being important. It defines how much you know about your spouse, how well you connect with friends and work colleagues, and how much you can influence and attract new people into your life.

There are many books on sub-communication and body language that like to pretend that the actual words coming out of our mouths hardly matter. I don’t believe them.

Like dull writing, dull conversation is stale, unemotional, cliché, routine, passive, and can trap you in a nightmare spawned from hell if you have no choice but to endure it.

The anticipation of bad conversation is the reason you wince and consider rejecting the call when that particular friend or family member’s name appears on your Caller ID. It’s boring because you can predict the entire conversation. The routine is stale and pointless – the conversation is going to do nothing except remind you that you would never choose to speak to this person again if you weren’t related by blood.

This also happens in our romantic lives. Here’s an imaginary but familiar conversation between a couple at dinner:

How was work?
Fine.
How’s Bill?
Yea, Bill’s good.
Did you call the electrician today by the way?
Yea.
Also we really need to get that new furniture sorted this weekend. Let’s go to the store on Saturday.
Ok. Have you decided on which sofa set you wanted yet?
No.

The questions are pedestrian. The answers are flat.

This back and forth can bruise your heart and wrench the life from your soul if you endure it long enough. Two people can talk, but both of them can know nothing about what’s really happening inside. Because not all conversation is connection.

I think conversations can change, and even save our lives. The best conversation is about encouraging someone else to dig out their soul and offer it up for examination. Here are some easy ways to encourage them:

1) Ask questions that give someone permission to open up emotionally

People are begging to express themselves to somebody. The film director Kevin Smith said people have three needs: Food, Sex, and the Need To Be Heard.

But people will be scared to open up for many reasons. They’re shy. They’re frightened of your response. They’re British… Which is why you need to give them permission to emotionally express themselves.

The easy way to do this? Ask them how they feel about something. For example:

“How did it feel when you beat your record in the marathon?”

“Was it difficult to deal with your parents divorce?”

“What was going through your head when they told you that you’d got the job?”

These questions prompt reflection on emotion. They cut through logic and ask someone to search their feelings, which makes them instantly feel more connected. An excellent recent Huffington post article talks about a couple who recently incorporated these kind of specific reflective questions into their relationship. In one quote the author, Glennon Melton, explains: “Questions are like gifts — it’s the thought behind them that the receiver really FEELS.”

I couldn’t agree more. Great questions make someone look forward to a conversation with you, because you are letting them speak about subjects and emotions they don’t usually get to talk about.

2) Use the Sigmund Freud Method

When a guy is opening up to you, be almost clinical in your responses. Do not judge. Do not criticize or noticeably gasp when he tells you something embarrassing or crazy or bad that he did. Make him feel like it is perfectly normal, then show him more curiosity. In other words, just give the other person room to speak!

Psychiatrists have the skill of being able to let someone speak and ask questions to prompt them to dig deeper. Be generous and probe for him to give more: What was that like? What else happened? Are there other things you are worried/excited about at the moment? Had you always wanted to do that?

People tend to reveal themselves when they feel like they (a) have PLENTY of room to speak, (b) won’t be judged for their actions, and (c) feel like you are curious to hear their answers. Do this and people will instantly feel at ease in bringing any conversation to you.

3) Give them a chance to be an expert

People want to share their wisdom. If you want someone to open up, just ask for his advice about what they love. This goes especially for guys who are ambitious and have lots of life experience they want to share.

Ask things like: “What would you tell someone starting off in your work today?”

“What’s the most important thing you learnt about yourself when you lived in that country?”

“What’s your routine for keeping fit/healthy?”

These question are interesting because they tell you about a person’s inner beliefs and perspective on life, which then let’s you share your perspective if you agree or disagree. People think they have to know a lot about what someone else does in order to connect with them, but it requires no knowledge: just ask them to teach you or give you advice instead.

4) Reveal your own vulnerabilities

Don’t be a model of stoicism or people will feel distant to you. Show that you’re human by revealing vulnerabilities and foibles. Nothing that says I’m a mess, but enough to say I have flaws, and I’m cool with that. As long as you say them with a sense of humour to show that you don’t take it too seriously, people will love you for it.

If you try to be too squeaky clean and perfect, people will feel alienated by you and won’t want to open up for fear of looking weak in front of you.

5) Change your stock phrases

If you notice yourself answering questions in the same way all the time, get yourself to be more honest. Ask yourself: What’s my real opinion on this? Why am I hiding it? Am I trying to play it too safe here?

Push the boundaries a bit further every time and you’ll get used to communicating with more honesty. Try to iron out any phrases you seem to repeat in response to questions over and over again and give a refreshingly honest answer.

6) Get someone speaking about what they would love to do

Engage someone by talking about their dreams and the big picture. Ask them what they would most like to have achieved when they look back on their lives, or what they would like people to say about them in the future.

The future is great, because it’s easy for people to get excited about their upcoming plans and you’ll learn a lot about their inner ideals when you ask them about their dreams and goals.

A conversation can change someone’s life. We can affect people in profound ways with the right question, or a truly honest response, or when we allow someone just to get something off their chest that they have never been able to say.

The world might love to talk, but it doesn’t mean everyone is having worthwhile conversations. We have to always be the exception, the beacon of truth amongst the dishonesty, the magnet of what’s real amongst the posing and superficiality. We have a chance with every word, in a world full of hot air, to be a person who talks substance. Or at the very least, you’ll get invited to more parties.

***

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75 Replies to “Easy Ways To Have Deep Conversations And Get Guys To Open Up To You”

  • I loved this article cause I get the conversation thing when I took a counselling course it taught me how to have a conversation and bring people out of they’re shell. One thing I remember in my class was there is a difference in hearing a conversation to listening. You know when a conversation is going well because you start in one place and end up in a totally different direction from the original conversation which I love!!

  • I think that this article is great and will help many people improve how they communicate with each other. However, I have problems talking to people, especially those who are potential romantic partners, because like you mentioned in #2 a lot of these skills come from Psychology. But I am actually working on a doctorate in psychology and often when I ask emotional questions or use active listening people ask you if you are analyzing them or (I hate this word) “shrinking” them. Recently I have thought that it would be safer to tell people I am an accountant, but then that would be dishonest. Lol

  • This is one of your finest, Steve. Poetic article, if there is such a thing.

    People always found it easy to open up to me. I mean, what is the point of being together with someone if you can’t open up to them and seek support and comfort in their company? I already have a protective side, but it comes out stronger if deep in a relationship. Outside world is full of vultures (oh yeah it is) and we all need that emotional protection mutually, whether men or women. Strong people watch out for their partners and give them inner-strength, whereas weak people only watch out for themselves, hence the judging, criticizing or they give you a flat face like a cow looking at a train.

    Thank you for this insightful article.
    Kiraz xx

  • Hi Steve,
    Thank you for such a detailed article on a subject that many, including myself, struggle with. You provide a lot of useful, important information. Do you have any tips on how to be more assertive? I struggle with finding the right words/responding appropriately when people act in a rude, careless manner toward me and later get mad at myself for not speaking up.

    Thanks,
    Liz

  • Steve,

    Steve,

    I ADORE Kevin Smith btw….so big ups for that.

    I heart this article. Brilliantly broken down – you could call it Charm 101: The Art of Conversation. This is what people fall in love with – when you acknowledge their special-ness and listen without judgement – just take them in and see who they really are and how they really feel. And of course, if they’re totally bonkers, that will come out as well. Excellent. Good way to screen up front. hehehehehe….

    Keep up the great work. XO

    Kelly

    1. That one statement about being bonkers is an excellent conversation starter. If I heard that come from a dates mouth, I would have to immediately ask them what they considered to be bonkers and see if their reply was based on an unwillingness to date outside of society’s norm or if the person was actually certifiably a danger to society.

      The rest of the date would be judged on their answer to that question and so would the future of anything thereafter.

      A lot of people have a habit of judging what they are not comfortable with, and if you happen to meet someone with high emotional intelligence with an ability to feel what doesn’t even register on most people’s radar, and you call them bonkers, well then, you have just lost an excellent learning experience along with any further opportunity of growing.

      As someone who is dating, I would beware the narrow-minded.

  • Dear Stephen,

    I just have to say that I hate being asked questions as a means of starting or continuing a conversation. When someone starts throwing questions at me, I literally want to run away. No joke, it is physically painful for me to answer questions about what I think or what I feel or what have you about myself when they’re not a natural part of an ongoing conversation.

    If you’re interesting (to me, at least) then you’ll say something that will spark a response from me, and vice versa. A good conversation should flow effortlessly from topic to topic and back and forth between the conversationalists. Questions will happen organically, but they’re not used as a prop to keep a conversation going or to get me to open up about myself.

    And you usually get a much more genuine response from the other person when a conversation is allowed to flow. When you ask someone a question, often the “right” answer is obvious and rote and not what the other person actually believes. But, if you can get someone spontaneously talking and expressing opinions or daydreams or goals then you get a glimpse of the real person.

    There is nothing that will cause me to lose interest in a conversation faster than someone asking questions as opposed to expressing their thoughts — other than utter inanity. Once, this girl that I’d just met started opining on the shape of her feet and then the shape of mine. I’m pretty sure the effort it took for me to sit still through that vapidity was visibly painful. Just thinking about it now makes me twitchy, and it’s been a good ten years since it happened.

    Of course, if a guy is super hot, I’ll answer all the questions he cares to ask. That seems obvious, but I feel like I should put it in print anyway.

    Best,
    Shannon

  • Hello from Ukraine, Matthew!
    I’m new here. I have recently started following your videos and posts. I really need your help… :)

    I met the guy let’s say 5 months ago 2 times only. We texted a lot until (as I have guessed already) I showed I was too interested. The thing is I asked him ocasionally to hang out 2 times thinking he was too shy to forward…and he agreed but then refused.
    I kept silent and he too. He never called me, wrote a couple of times and we had a wonderful …again texting. I watched your videos that texting sucks and I could agree.
    But IS THERE ANYTHING I can do to understand whether he likes me or not and should I completely forget about him or do something.

    Looking forward to hearing from you, Matthew
    Have a nice vacation in Cyprus by the way ;)

  • Really excellent writing, Stephen. I liked when you were mentioning reasons he may not open up and then said, “He’s British.” That was coy and smart :)

    Excellent advice – I’ve been working so hard on surprising everyone all the time so it was poignant for me right now.

    It made me think of our first conversation at the retreat – you said you hadn’t met me yet and I asked you about your role models, as that’s what we were talking of. You mentioned F. Scott Fitzgerald and I looked at you like you were crazy and you said – “Well, his mind.” And we both laughed and I loved that we both knew why you wouldn’t want to follow Fitzgerald in any way but his mind but we didn’t have to say it. I felt super connected to you after that short conversation and I immediately liked you.

    Much love! Keep it up! I love reading what you write <3

  • Good article but no thanks. To let a man who doesn’t know me , giving me an advice when I don’t need it? It’s none of his business about what I do, he shoulda watch his own.

  • I have been doing the on again off again “online dating.” I was about ready to give up on it again when I got a message. What set this message apart from all others was that the guy asked my ethnicity. To me it seemed obvious (Hispanic) regardless I answered his question and his reply was “wow now that you tell me I can see it, you have beautiful eyes I thought you were Asian. Do you get that often?”
    Our conversation went from there about our ancestry and then he said “it seems that you put thought into your responses I like that.” He then asked about my beliefs, was I religious and I thought is this ok? Should we be talking about this? I’m an open book, so we talked about religion and just as quickly changed the subject and asked about my thoughts on an ideal relationship. We “argued” on the topic for a while.
    I had to stop our conversation at a certain point and before we agreed to talk again he said I think i like you. I haven’t talked to you in person but just from your responses I like hour genuine you seem. To be.
    The next day we talked for hours and asked for my # and wanted to Skype but I wasn’t ready so I said no. Naturally he asked why. I replied simply because I don’t know how I feel about you. I don’t give my number away freely. He stared to ask questions again but this time instead of having that playful charisma it started sounding more like an interrogation. It came to a point where I was so overwhelmed that I let something personal slip. He said. “Okay maybe you were right… I’m sorry you were trying to tell me. I’m just such a curious person and I find you so interesting. I don’t think this is going to work out though.” I agreed, I said too much on a 2nd conversation! So I said I’d unmatch us and right when I did he messaged me “wait. Let’s keep talking.” Too late. He gave me his # but I don’t have the nerve to call him it’s been 3 weeks. Regardless of how quickly that escalated he was great at conversation.

  • My boyfriend is in the military. I’ve tried all of these without luck I just need a spiritual connection again. I used to have that. We used to have that. Now it’s routine and awful because he just doesn’t have any opinions on anything.

    1. Everyone has opinions, and I’m fairly certain he is no exception. I’m no expert, but I’m guessing one of two things is going on: either he is incredibly busy/tired/possibly depressed/apathetic or he is shutting you out for some reason. Examine the relationship from your side of things first and see if you can pinpoint any triggers that might cause him to shut down instead of opening up and sharing with you.

    2. Those who don’t have “opinions” are lucky in the way that they are not entangled and caught up with judgments in life

      Just chill.

      Seriously, everyone needs to just chill.

      As we chase some so called idea of perfect, we have lost who we are. When I was 20, I was rough – politically incorrect – a social disaster. And people loved me just the same.

      Smoothness is like an onion. No matter how many layers you peel back, it is still an onion.

      Be something else.

  • THE BEST article I’ve read in a very long time. I’m all about connection and communication. Connection is the most influential, driving force in my life. So this article really speaks to me. Thank you, Stephen…for something so well written. You did great sharing thoughts and emotions and insight—-“British” aside. (-:

  • I absolutely believe this line, in my soul. If you truly believe what you write, it is refreshing to know that a man could feel this way:

    “I think conversations can change, and even save our lives. The best conversation is about encouraging someone else to dig out their soul and offer it up for examination.”

  • What do you do if the guy doesn’t WANT to open up. …he just skims the surface of relationships. …its bloody frustrating! !!!!!

    1. As much as I (thought I) love(d) dissection, I would much rather not dissect myself. Yesterday I gave a presentation, got super nervous, totally “messed up” and I smiled at the end of it!

      Because the “worst” was over. Then 10 minutes later, I was talking back to normal, giving suggestions, “bouncing back” where there was nothing to bounce back from.

      You can be the most nervous, quiet, “introverted”, whatever other non-“idealistic” quality you want to insert here and still be perfectly fine and respected as an effing human being.

      Why does no one wake up in the morning and say “I want to be me”
      Today that may be “bad” at conversation
      Tomorrow it maybe “bad” at dates

      I don’t care. Concentrate on expression, not impression. Or you’ll end up with knots in your abdomen like me. I just want to get laid

      I know this probably doesn’t make any sense but this is not my real name and I can say whatever I want

      Good luck to all of you, remember you can always press the Exit button. Life is short. Eff this shit

      Stay Steady.

      1. The last couple of lines were a bit much. I am sorry

        I feel weird since a while and I am like I don’t care but I miss when I cared. But I don’t care and it’s like why don’t I care and then I Just laugh and I feel mean but then I just laugh again

  • Wow excellent article! You are amazing Stephen… :) gave me goosebumps on how true it is what you say about conversation.. Love your work.. Keep it up… Amazing!

  • What if the person you are with is the one who isn’t asking many questions? Perhaps they show interest through listening but aren’t good at inquiring. What can you do? Do you think this should automatically discount them? As someone who thinks questions are important as they convey interest I have a hard time adjusting to the fact that many people, particularly tech nerds I have met, communicate differently.

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