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?
How’s Bill?
Yea, Bill’s good.
Did you call the electrician today by the way?
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?

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

  • Love this topic!!! ^_^
    I think im a people very easy to talk because im always in a good mood (generally)..and people always see me like a happy person! :)

    when you describe a conversation BORING..like how are you, how is bob or something…thats really what im always afraid that could happen to me!!!
    because when we want to make a good impression or interested in a guy that.s hot…talking becames really hard!!!

    well..normally not in the first dates, but after i kind do something that people might think its a game…
    but to make easy to talk to other half and keep the connection and go on, so… after a hard day..im always like:
    *so, how your day went..tell me one thing funny or two that it was good today?(a funny thing, ou just curiosious)?

    When they dont know really, i go first..i always have tinny things i love, i work with children and they always make my day brighter..but sometimes the positive or funny thing is just kind person that help me on something or i won something on a store…simple things!

    And then, the other person remembers a cute thing too..and then he is in a good mood and feel closer to you, because he is sharing a “piece” of his day .. becomes more emotinally and the toppics can change easilllllyyyyy, but then you two, are more in a intimate “place”..

    THE BEST is…that, the next day he will think of you, because when something cute happen or good, he will be like..-i have to share this with her! :D

    :) kiss*

    1. Thanks for commenting Agostinha! You touch on a very good point here – it’s much easier to get someone else to open up when you do give them an example of it first. We always have to lead with our state of mind, and make someone feel comfortable in our presence before they’ll feel happy to express themselves authentically. i.e. you can just meet someone and launch straight into a story: e.g. “the funniest/weirdest thing happened today, I’ve got to tell you…”

      You sound very fun and warm so I’m sure you have no problem doing this ;)

      Take care,

      Stephen x

  • this is so useful!! I really love your blog. I have a date tonight and I might use this.

    thank you and your brother Matthew for all the information. It is not being single nor in a relationship. you give us clear guidance.



    1. Thanks so much Renée. Glad you’re going straight out to field test the techniques on a date. That makes me happy to hear ;)

      All best,

      Stephen x

  • Thank you Stephen for this great article.
    Every Wednesday I get up sooo excited to find out what will your article be about. Always so inspiring. I recently used to ask this type of questions when I am on a date with a potential mate or to parties with people I mostly don’t know.
    It works quite well. Conversations are way better!

    I have to thank you a lot! A few weeks ago, I talked to you about this dream job in Dublin (I’m French) I wanted. You advised me to show more what I could bring to the people hiring me.

    I sent 3 questions to the manager a week after the interview, with really helped me to be on short-list:
    – What are the 3 main qualities you are looking for in a collaborator?
    – Will the company offer training for the marketing assistant during the 2 years?
    – How will you assess the job is filled with the right person? What are the evaluation criteria?

    Then, I had a final interview with the CEO.

    and I got the job!!!!! I’ll move to Dublin in a month.
    I was supposed to attend Get the guy tour in London in February, I had to cancel last minute as I couldn’t afford the way back and forth. It terribly broke my heart! U can’t imagine.

    But that time, I’ll come to see Matt mid-June in Dublin. Hope you will be there too, to thank you in person and have a meaningful conversation. ;-)

    Take care! U’re amazing!

    1. That’s incredible news Noémie, congratulations!! I’m so pleased and excited for you!

      Thanks so much for enjoying the articles; it makes me happy to hear you look forward to them since I really try to make them valuable to read.

      Unfortunately it is unlikely I’ll get to Dublin for the upcoming event as I have an extremely busy couple of months coming up, but I hope to get to more events soon! I do a couple of retreats each year, but i’m not really on the tours right now.

      Well done again on the job. Really excellent work. Now go celebrate! :D

      Stephen x

      1. Thank you Stephen!!! Yes, I am so excited too. I’ll often read this article when I’ll be in Dublin as I will meet a lot of new people. I really want to integrate and make new friends quickly. “Every relationship begins with a conversation”
        Oh okay, I understand for the event in Dublin. :-( :-( :-(
        D-2 before your new article. Can’t wait!
        See you on Wednesday!!!


  • This very topic has had me thinking all week as I’ve been watching series one box set of Mad Men. The scenario of man/wife conversation you illustrate is played out between Betty and Don. He has all these emotions swimming round his head from his childhood coming back to haunt him, but it’s not his wife he opens up to. I know this is fictional, I’ve not lost the plot just yet! Same scenario, Lost in Translation. I saw the film a long time ago but I think the film centres around the main characters conversation.
    I agree with what you say and your suggestions I will think about. I do think we have more of a connection with some people to start with, which does make it easier. Not to say it’s not worth trying as with no connection there’s no relationship really. It can’t just be sex, can it? Actually that’s no good with no connection, even if it’s not many words. Lol x
    Not sure any of that makes any sense.
    Another great piece of thoughtful writing, you really do show your intellect through your writing.

    1. I love Mad Men, and Lost in Translation! You have excellent taste Kathryn.

      And yes, even sex requires some good conversation (maybe beforehand to put you in the right mood ;)

      Thanks for your kind words about the writing, Stephen x

  • Thanks Stephen yet again for an interesting article some of these conversation techniques I was taught when I was in a counselling class but, its good that you refreshed them for me as I don’t always get to use them. I find sometimes when you are conversing that silences aren’t always bad either but people get nervous if there isn’t conversation all the time. I find that silent break sometimes is just a way of saying that I am comfortable in your presence that we don’t always need to have continuous conversation!

    1. Totally agree Beth. Yea, we all need reminders of how to have good conversation, it takes practice and is easy to slip back into boring stuff.

      Take care, Stephen x

  • I really enjoyed this article and I actually have recently been around a guy who asked questions like this and it was awesome. However, I try not to do some of this especially #2 because I am a Psychology doctorate student and people often think you are analyzing them if your questions are too Clinical, feelings, based, or probing. So I think it has to be a very fine balance.

    1. You’re right Mj – people start to get nervous and weird if they feel analyzed. That’s why you have to explain why you’re asking the question and make it feel casual and natural. You want him to just feel like it’s interesting conversation rather than like he’s being tested. Come from that place of intense curiosity and don’t make him feel judged and you’ll be fine.

      Thanks! :)

      Steve x

  • Libre the article Steve! Very useful as I’m really interested in meaningful conversations without been seen as too intense. You’re a gifted writer! :)

    1. Exactly – being deep doesn’t mean being intense. That’s the perfect balance to strike.

      Thanks for the lovely words Ana.

      Steve x

  • I look forward to these every Wednesday too!

    I actually am good at asking deeper questions. I’ve tried just listening but when I’m quieter the conversation peters out.

    Sometimes it’s like tennis and the guy just won’t volley back no matter how you try to draw him out. But then I guess that’s not the guy I want, though!

    Sometimes guys don’t think that deeply, though. I remember asking a guy what he was passionate about and he really couldn’t think of an answer. Oh well!

    1. Those guys sound rubbish A! It’s a good test to see how imaginative someone is – I find it to be really effective in showing if someone is thoughtful, so don’t be afraid to get deep quickly (as long as it doesn’t sound like you’re interrogating him or doing some weird psycho-analysis!)

      All best, really glad you look forward to reading these articles.

      Stephen x

  • ❤ ❤ ❤ :) ROMANTIC HEART BEATS :)❤ ❤ ❤

    With all my heart I thank you for everything heart-touching :)I’m truly touched and deeply moved by true ROMANCE on planet earth :)

    May I say:

    ❤ Je suis d’accord :)❤
    I loooooooooooooooooooooooooooove the Hussey brothers ❤&❤ deep conversations :)

    If true LOVE is the message you can always have deep heart-touching conversations :)

    The most beautiful moment is when you feel his/her every HEART BEAT :)
    When everything you feel for each other is true LOVE
    When you kiss each others HEARTS with true LOVE :)

    Oh dear ROMANCE :) That’s loooooooooooooooooooooovely :)

    May I play romantic music ❤&❤ say:

    If I meet Mr.Right I’ll have deep heart-touching conversations with him :)
    ❤&❤ enjoy the moment when feeling true LOVE for each other ❤&❤ every romantic melody of HEART BEATS ❤&❤ HEART KISSES ❤&❤ … with him :)

    I’m so so so so so so so excited :)

    How about all conversations on planet earth? :)
    Why does not everybody enjoy deep conversations?

    I believe “Easy ways to have deep conversations and get guys to open up to you” will open hearts for romantic deep conversations :)

    May everybody read this article to enjoy true ROMANCE in future :)❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤❤

    may we open our hearts ❤&❤ always enjoy deep conversations :)

    ❤ Romance je t’aime de tout mon coeur :)❤



  • Monsieur Romance:

    Chaque moment, Je vais courir à l’endroit romantique:
    Votre coeur :)❤

    Les battements de nos coeurs ❤
    Sentir le véritable amour dans nos cœurs❤
    Embrasser nos cœurs ❤
    Vraiment aimer ❤
    c’est la vie :) ❤

    Every moment I will run to the romantic place : YOUR HEART :)❤
    Our heart beats ❤
    Feeling true LOVE in our hearts ❤
    Kissing our hearts ❤
    Truly loooooooooooooooooving ❤
    That’s life :) ❤

  • I’ve composed a song for Mr. Right :)
    If I meet him I will sing :

    Chaque moment, Je vais courir à l’endroit romantique:
    Votre coeur :)❤
    Les battements de nos coeurs ❤
    Sentir le véritable amour dans nos cœurs❤
    Embrasser nos cœurs ❤
    Vraiment aimer ❤
    c’est la vie :) ❤

    + I’ll say:

    J’aime les conversations romantiques ❤
    Je les aime de tout mon coeur ❤
    vous voulez me parler? ❤

    Dear wonderful Hussey brothers,
    May I thank you very much for this romantic topic :)
    Merci beaucoup pour tout l’amour :) ❤

    1. May I sing:

      Mr. Right, I believe we will meet in a place called true LOVE : In our hearts :)


      God knows where ❤&❤ when we will meet on planet earth :)


      What I know is: I loooooooooooooooooooove Mr. Right :)
      ❤&❤ I’d loooooooooooooooooooove to meet him:
      on planet earth ❤&❤ in heaven :)

      If it’s possible to meet somewhere on planet earth God knows I’ll be there with all my heart :)
      When we live forever in heaven we have endless possibilties to meet :)

      In the name of true LOVE, may something heart-touching happen :)

      1. I’d truly loooooooooooooooooove to come to your live-event :)
        Hope you can reserve a seat for me :)

        May I say:

        I’m not very good in earthly things, like using paypal.
        If you ask me to play the organ I know how to play a song in a second :)

        If it was possible to buy a ticket by playing a song on the organ I’d have bought a ticket in a second :)

        Well then, I’ll try the paypal system again :)
        If I’m lucky it will work this time :)

  • I’d truly loooooooooooooooooove to come to your live-event :)
    Hope you can reserve a seat for me :)
    May I say:
    I’m not very good in earthly things, like using paypal.
    If you ask me to play the organ I know how to play a song in a second :)
    If it was possible to buy a ticket by playing a song on the organ I’d have bought a ticket in a second :)
    Well then, I’ll try the paypal system again :)
    If I’m lucky it will work this time :)

  • Stephen, this one is great! If I may say one of your best pieces this far!

    It’s all about wanting to know the person on a deeper level. I truly think we can get deep conversation with about everybody with the right questions, assumed they want to share their life with us.
    You could have a casual conversation or small talk with someone and then BAM the right question leads to a deeper conversation and both wonder how they got there but have more fun talking to eachother. So, maybe we haven’t found the right questions for the people we avoid or we just don’t get along with them due to other reasons than the willingness to open up to them.
    So true – If you want a deeper conversation, you should get ready to get vulnerable yourself.

    Happy Easter Holiday in advance!

    1. Happy Easter to you too Irene! :)

      Always a pleasure to hear from you. And yes, it’s so easy to elevate our conversations, which is why I really wanted to take on this topic. Thanks! x

  • What I looooooooooove about deep conversations: HEART BEATS :)

    The deeper you go the more you see & feel in your HEART :)

    How deep can we human beings go? :)

    May we go as deep as we can go :)

    Every moment I’d looooooooove to dive into the ocean of LOVE to feel the warmth of ROMANCE with Mr. Right :) &
    Kiss the fish of PEACE & LOVE & WISDOM
    With everybody I looooooooove :)

    Looking forward to all the beautiful oceans of LOVE :) & Being at the most romantic places with Mr. Right : A place where we can truly looooooooove each other & kiss each others HEARTS with all HEART :)

    Have a heart-touching dive everybody :)
    I believe Matthew Husseys live-event is one
    of the best places to dive into romantic oceans :)
    So everybody is gonna have a truly romantic time ;) Yay :) Great thanks to the LOVELIFE hero & his lovely team :)



    1. May I say:

      This is one of the best articles I have read in my life ;) Thanks to all of you I’m having a truly heart-touching time :) Hope everybody too :)
      Thank you so so so so much :)
      I looooooooove to read & write :)
      Writing here reminds me of playing tennis & snooker & lawn balls at the English club in Hong Kong :)
      The English I know looooooooove moving on the court :) & they move so so so well :) That’s why I always enjoy English sports :) & now got to know two romantic brothers who know how to move with HEART :)How heart-touching :) I’m deeply moved :)


      1. Now I know why it’s so amaaaaaaazing here :)
        This is like English town :)

        If China towns exist, I believe English towns exist too :)

        Wow, this is a place where you can say what you truly feel & drink English tea :) Splendid :) & Looooooooovely <3<3<3<3<3

  • Great article!!
    These tips are sooo true and sooo useful for having a deep and honest conversation,which will help to become an ideal interlocutor for a guy:))
    Matthew, actually right now i am reading your book its amazing i loooove it so much!!!!
    I am from Belarus and still waiting for Russian version of ur book(because of some difficulties in translation hahaha)
    Happy Easter!!!

  • Having deep conversations is easier for me, than having small talk and making jokes. I listen to people, (most of the time) understand their jokes, but it is hard for me reciprocate. That is why I often have hard times finding friends in the beginning, because one can’t immediately dive into the deep stuff.
    A coaching program said one should memorize a couple of jokes and use them by default, but somehow I find myself so dry telling them, not convinced enough or using an incorrect tone… self-evaluation happening here… new friends even joke about the fact that “oh, Nicole, is going deep again”, when I ask about things that were listed in the article.

    My best friends are people who I’m together with since 1st grade and we grew up together i.e “by (having) a long string of experiences and conversations about those experiences” so conversation happens naturally. I have a harder time being easygoing with new people and don’t know how to change this. What if understanding eachother is something cultural? I move around a lot. In Germany I attract new people by being open, warm, and trying my best to be funny (opposites attract), but here in the UK I’m sort of behind on all conversations that are happening. Maybe I should do a change of country since you fired a ball at “British”xD I find myself making best connections with Russians and Italians abroad, because I can fetch my experience from the past, feel familiar and have a common way of communicating? This year I will be living in Russia and later in Canada, let’s see how connections will be made there… And Russians abroad are completely different people than Russians inside the country, I’m a little nervous in how to tackle new connections which are going to be lasting rather than superficial and only in the moment.

    Great article xxx

    1. Hi Nicole,
      I have a very similar problem to you; for me it is all about the “deep conversations” with new people, which of course take time to happen because no one talks about deep stuff straight away. Small talk I have little patience for, especially because even when I do like it, it makes me wait longer until I see whether someone can talk about deep stuff or not (most people can’t; they either haven’t had deep experiences -most- or they feel somehow weak talking about deep stuff).
      This is slightly off topic but I am so curious about what you said about Germany. I’d love to know how you got along there (were you there studying?),and how long you were there for. I have just moved to Munich from another European country (maybe you were in a different city and it makes a difference), and while I love it here, I find it hard to make connections, despite being open and warm.
      By the way, communicating in such a deep level, while being a royal pain in many ways, also gives us empathy and sensitivity, and those are beautiful gifts and tools to see life with :-)

  • Great post! One of my favorites to date. I know from a female perspective, boring conversation is one of the first things to make me think, “next…” when it comes to a guy. Thanks for the tips!

  • This is one of my favorite posts yet! Conversation really is the key to living a truly exciting life; it’s all about the connections built between people. Being a genuinely curious person is one of my greatest assets in life because it has made me good at listening and asking questions. Now I just have to get better at being as open as most people are with me as they answer my questions. A work in progress, I guess :)

  • Unquestionably believe that which you said. Your favorite reason appeared to be on the net the
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    You managed to hit the nail upon the top and also defined out the whole thing without
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