I Want to Have Deep Intimate Conversations But Dating Seems So Shallow.

woman walking down the stairs thinking about having deep intimate conversations on a date

First I want to thank you for all your great work and insights. I came across you only a few weeks ago but have since been devouring your material including your book, “Why He Disappeared.” In doing so, I’ve realized the major mistakes I’ve been making in dating. These usually occur for me in the relationship phase before attaining love. I often find myself wanting to achieve higher levels of emotional intimacy with my partner but realized that I have been pushing too hard (or in some cases have just been with someone incapable of meeting that need).

I have also realized that having deep intimacy is a basic need and desire I have, which I reflected clearly in the close relationships I have with family and friends. I just don’t do casual and superficial well. It feels like a waste of time and is highly unsatisfying.

I just came across the concept of “Deeper Dating” by Ken Page. I am currently working through the steps in his book. I would like to hear your perspective on reconciling the tenets of deeper dating (openness and establishing intimacy as a point of departure, rather than as the end point of a waiting game) with the seeming infinite patience required to not pursue men, not discuss relationship status/marriage, and not push a desire for emotional connection on men while in a relationship as not to scare them away. It seems these perspectives are mutually exclusive. Is there something I’m missing? Is it possible to start from a place of deep connection with someone, discuss your true desires for your romantic life (including marriage, children), and not scare them away?

I really appreciate your insights as I have been so dissatisfied with dating at the surface, but it seems this is the recipe for eventually getting into a relationship. However, I also wonder if this is a recipe for lasting relationship. Thank you for your response and thank you for your work!


Confession: I have a copy of “Deeper Dating” sitting on my desk, in the same pile as “The Love Fight,” “Why We Pick the Mates We Do,” “The Seven Principles for Making Marriages Work,” “How to Gracefully Exit a Relationship,” “The Pathway to Love,” and “Love Me, Don’t Leave Me.” Authors send me books in hopes that I will blog about them, and I’d really like to…except the last thing I want to do at the end of the work day is read more stuff about dating and relationships. No disrespect to any of the authors, who are undoubtedly bright, talented, hardworking and insightful. I just work from 9-5:30, play with my kids from 5:30-7:30, eat with my wife from 8-9, and after that, it’s TV, or fantasy sports, or a book by Jonathan Franzen or Donna Tartt.

Long story short, it’s dangerous for me to comment on a book I haven’t read, even if I suspect that I’d agree with Page on many things in principle. So let’s take a step back and look at this through a few different lenses.

Sometimes, you gotta lighten up a bit.

I’m a lot like you. I don’t do shallow. I’m incapable of it. I was voted “Most Intense” in my college dorm. I’ve had friends say to me that I tend to “plumb the depths of their souls” when we talk. And while these folks are being honest and teasing me, they have a very valuable point. Sometimes, you gotta lighten up a bit.

Being intense and going deep absolutely has a place in the universe. Long-term relationships can’t be solely based on common interests and great sex. At the same time, the kind of intimacy you seek is something that tends to grow over months and years. It seems like you want it all up front, which a) isn’t always realistic and b) isn’t always accurate. Meaning that lots of people are not as intense as you, and that’s okay. In fact, they might be a really good balance for your intensity. Furthermore, people who ARE as intense as you may go deep right away, but sometimes that intimacy can be an illusion. I can have a great 5 hour conversation with a stranger on an airplane, but that doesn’t mean we’re compatible. It just means we were never going to see each other again, so we let it all hang out and got real in our first meeting. I would guess you tend to assign greater meaning to going deep than it should really be assigned.

The first serious girlfriend I ever had (which was, for me, a 5 month relationship during my senior year of college) taught me this lesson herself. I had waited so long (21 years) to find someone to love that within 2 weeks I was wondering why she didn’t love me back. Her answer was blunt and patient: “It’s been two weeks. We will continue to grow and deepen our relationship as we get to know each other over time.” She was dealing in reality. I was dealing in fantasy.

Lest you think I’m trying to push you in the shallow end of the pool against your will, I’m not. I’m only telling you the same thing I would tell anyone, male or female, in any situation: is your methodology effective or ineffective? Is your way working or not working? Because it doesn’t matter if you like it or if it resonates or if it makes sense to you. If you take it out for a spin in the real world and no one is responding to your desire to get intense from the get-go, well, then, maybe you have to adjust and find a middle ground that works better.

By forcing intimacy, you create the conditions for a deeper, better, more memorable date. But that doesn’t mean that the intimacy has greater meaning, nor does it mean that people who don’t choose to go deep are incapable of it.

This New York Times piece made the rounds last month precisely because of the reasons you outlined. You’re more likely to feel connected to someone when you discuss intimate things than when you discuss the weather and movies. I agree wholeheartedly, and I even took the attached 36-question quiz with my wife on Valentine’s Day. They did, in fact, reveal things we’d never even discussed, and brought tears to both of our eyes at points.

And that’s the irony of the title of the piece “To Fall in Love with Anyone, Do This.” By forcing intimacy, you create the conditions for a deeper, better, more memorable date. You see the humanity inside every man, and get beyond the general biographical patter that dots most early dates. But that doesn’t mean that the intimacy has greater meaning, nor does it mean that people who don’t choose to go deep are incapable of it.

Without reading Page’s book, I can’t comment on the steps that he’s suggested. What I can say is that good dating advice has to be applicable to people in the real world who have not read dating advice. My suggestion is that by doing everything in moderation — mastering both small talk AND deep talk — you maximize your chances of making a deep connection with the greatest number of people.

Join our conversation (25 Comments).
Click Here To Leave Your Comment Below.


  1. 1

    I’d like to offer a different perspective on this.   I also really dislike shallow or casual, etc.   I really like deep and meaningful.   However, I am also a very reserved and private person.   You wouldn’t know it to look at me because I can be very effusive in a group of people but all the information I offer to strangers or casual friends is well, casual.   I couldn’t possibly make that sort of deep connection with every other person I meet because 1) it would be exhausting and 2) it has not been earned.   I’m definitely not saying that this is a good or better way to be but I am hoping to offer some food for thought.   Over time, I have come to recognize the problems with my approach.   For me personally, the danger lies in holding back too much or for too long.   The ideal place to be is probably somewhere between the OP and me.   I find that emotional intimacy that’s developed over time is of the richer and deeper variety rather than when it is forced upfront.
    I think it’s possible to strike a balance between “spill your guts out” and inane, insipid conversation.   In the early days of a relationship, it is very important to understand the direction of your partner’s thoughts, his/her approach to solving problems and the things that are important to him/her.   This doesn’t have to focus solely on marriage, children, finances and other serious “make or break” relationship topics that can be scary early on.   Does your partner like animals and how does he treat them?   What is her favourite childhood memory?   If he had a million dollars, what would he do with the money?   Does she think about world hunger and how to solve it?   Maybe I was kidding a bit with that last one :).   My point is, it’s possible to deepen emotional intimacy without tackling the big questions right away.   It will probably give you a feel for the person and you can guess at his/her answers to the big questions before you actually ask them.

  2. 2
    In Not Of

    I tend to be like Skaramouche. Google “talkative introverts” and lots of interesting articles pop up.   

  3. 3

    Very few men want deep, intimate conversations.   Do that with your girlfriends.   Men want sex and fun, and maybe if they really get to know you, you might have a deep conversation every once in a while.   It sucks, but that’s how it is.   I was in the Army and worked as an Engineer for 20 years.   Men are not women.   They don’t sit around talking about deep things.   Perhaps they used to during the time of Pliny the Elder and Plato, but these are not those times.   I think men are capable of profound thinking and emotion, but our culture has murdered that side of men.   You’re fighting an uphill battle if you expect a man to be deep and intimate with you because it scares them away, and they all seem to only want their freedom these days and not deep ties to a woman or family.   I don’t really blame them.   I blame the brainwashing on TV and movies.

    1. 3.1

      This certainly is not true in my case.   As a man I actually do like to have deep and meaningful conversations.   Which, given I got my degree in philosophy, is not surprising.   My personal weakness is if I don’t check myself I can go on and on with a subject that I’m passionate about and absolutely dominate the conversation.   Then it becomes less of a coversation and more of a lecture.   And that’s the last thing I want in any conversation I want to have with someone, especially on the first few dates.   So perhaps it’s less of a situation of men not wanting to have deep conversations and more about them holding back so as not to dominate the conversation or bore their date or female companion.

    2. 3.2

      Sure men like fun, but as a guy, I will disagree with you. I may not like having very deep conversations with other men as it feels too personal and crosses lines of stoic masculinity, but I do like having deep conversations with women, especially if my attempt at an intimate connection is being reciprocated.

      I will gladly share deep personal thoughts with a woman if she is willing to do the same. I may not do it all the time and it’s good to intersperse deep conversation with lighthearted trivialities, but I certainly will not be scared off by emotional sharing.

      I do want deep ties to a woman and a family. I just have to make sure I find the right woman. To me, “freedom” gets old. I’d rather have a companion to do stuff with than try to remain single for as long as I can as if it’s somehow a better deal.  

    3. 3.3

      Wow, this has not been my experience.

      I have met more men who wanted to have deep and meaningful conversations with me – far more – than women.

      In fact, when I open up about a “deep and meaningful” topic with a man I have had the experience where their eyes light up and they lean forward in their seats and come alive so often that it is scary. Society expects men to be superficial, and in doing so does them a great disservice.  

      1. 3.3.1

        I’ve had similar experiences, @Clare3.3.   Many men I’ve met dating have seemed almost starved for meaningful conversation and deep connection.   

      2. 3.3.2

        Clare, I agree on it word by word. It’s as if some women expect it. But, at the very same time when the situation arises. You see how scared they get & also run away.

    4. 3.4

      Certainly men are capable of such conversations. You have to earn that privilege however.

      1. 3.4.1

        And we know we are subjected to hard scrutiny and judgement.

    5. 3.5

      I disagree somewhat.

      There is a facet of masculinity that is endlessly promoted, true. The tough, sports loving, plain talking, meat and potatoes regular guy who wouldn’t be caught dead talking about anything deep. That’s one facet of traditional masculinity, indeed.
      But it’s not for nothing that the greatest thinkers, makers, inventors, religious figures, atheist figures, war mongerers, peace makers etc are men. We certainly have the capacity to go very deep and a significant minority of us do go deep, very deep.

      Women’s conversational interests tend to differ from that of both types of men above.
      They’re certainly not into the powertools and the touch downs, but women’s aren’t that much into the latest programming language or the latest musings about a possible silicon-based lifeform on Mercury either.

      I’m the kind of guy who is always, always ready for deep conversation on serious topics. Not because I’m pretentious but because I’m interested in a lot of things, basically.


    6. 3.6
      Lauren Wilder

      Repeat after me, “Not all men are engineers.” There are loads of men who are great with words and emotions. In fact, you aren’t even doomed as an engineer, but that particular school and work culture does enforce a ruthlessly rational way of being. Please don’t think that way of being even approaches the majority of men.

  4. 4

    Hi Evan,   I get an error when I try to access the questionnaire you mention and inserted a link for.    I I’d love to take a look at the questions if tee link could fixed.    Thanks so much for this and ask your advice!    

  5. 6


    I understand your desire for intimacy and depth in a relationship, I really really do. Quite frankly, the idea of a superficial relationship with a partner for the rest of my life makes me want to put a bullet in my head.

    But, pace yourself. The kind of intimacy and deep knowing which lasts develops slowly, and takes time. And it comes through shared history and experiences, overcoming obstacles together, solving conflict, compromising – much more than it does from discussing the meaning of life. No one is saying you have to date people who don’t have the capacity for depth and intimacy – don’t do that – but if you meet someone where you sense the capacity is there, give it a chance to grow.  

    1. 6.1

      Again, I agree with you, @Clare.   True depth of mutual understanding needs time to develop.   When guys tried to have intense conversations with me on the first or second date, I saw red flags: too much too soon!    I preferred if I get a sense, early on, that this was a thoughtful, interesting man who had potential for profound talks in the future.   Then, slowly, we could share our ideas and feelings with each other as our relationship developed.

      @Evan: LOL about the letting it all hang out with folks on airplanes.   Whenever I travel, I have incredible chats with strangers; so easy & delightful to open up with someone when there’s nothing to lose & knowing our lives will never again intersect.   This is a kind of “insta-intimacy” is fun but no match for the kind of true intimacy that builds after weeks, months and years of opening yourself to someone.

  6. 7

    AFAICT the letter-writer doesn’t say how long she’s been dating the guys she’s been expecting to have deep intimate conversations with before they bug out.   She says she has very close relationships with family and friends…but she’s had years to develop those relationships–a whole lifetime in the case of family.   She can’t expect to date someone for a few weeks (à la Evan’s college GF) and expect them to be ready to bare their soul to her.

  7. 8

    You’re fast forwarding.   You want to get to the end of the book and skip over the beginning and even the middle.   Relationships happen over time, they change and grow.   Your connections with people change and grow.   The expectation to have a deep connection with a guy, similar to one you have with friends and family, is unrealistic and unreasonable.   Remember, it took years to deeply connect with and trust other people in your life and the same is true with a boyfriend.   First, get to know someone and understand whether or not you like that person.   Get to know the person.   Over time, the connection will deepen.   It won’t happen overnight.    If you connect quickly and intensely early on, it can trick you into thinking that you’re compatible with someone when you’re not.   Plus, intense beginnings usually fizzle.    Bottom line – figure out whether you click – do you share similar views on the things that are important to you.   Once you get to know each other on a basic level, your relationship will deepen.    Slow and steady wins the race.

  8. 9
    Karmic Equation

    Deep, intimate conversations aren’t indicative of a man’s ability to be a good partner.
    Deep, intimate conversations aren’t even necessary to make a relationship work.
    Feeling connected to a man during extended silences, with each of you deep in your own thoughts, without feeling that the silence is “deafening” but rather “soothing and peaceful.” That’s a better indication of your compatibility with a man.
    If you look at yourself in the mirror, this need for you to have “deep meaningful conversations” is your way to pat yourself on the back. You want to be perceived as deep. But as I said, just because you are, you may not be relationship material.
    You want intelligence and you want an articulate man. But what you NEED is a man who can express his feelings for you and towards you in a way that is natural for both you and him. If he doesn’t debate the difference between Dante’s Inferno or Satre’s No Exit, who cares? His ability to talk “deep and meaninfully” about existentialism isn’t going help you change your babies’ diapers. You know? Get real with yourself. It’ll be a lot easier to find a man then.

    1. 9.1
      Karmic Equation

      Bad English,
      “Just because you believe you are [deep], doesn’t mean you’re relationship material.” — is what I should have written.

  9. 10


    I think this is a great post! I totally agree with you. Deep intimate conversations have their place. And so to does cheerfulness, boldness, confidence, playfulness, contribution and connection have their places. Learning about one’s value hierarchy and what feelings a person is really after is key: is it recognition, contribution, love +warmth, significance? Dating should be deep and meaningful but relationships in both love and life should be multi-dimensional and include humor, playfulness, confidence, boldness, contribution and connection. There is a time and place for everything : )

  10. 11

    I’m wondering what the author means by wanting this deep intimate relationship and conversations right away. I’m just not sure in exactly what ways she means…With upfront intensity (just from my own experiences) it can bring unexpected side effects -although it can be wonderful in ways too. If I’m dating, I try to keep things light and fun nowadays. I think I naturally can easily get into more depth in conversations. And, people talking to me, feel pretty comfortable and sometimes they get way too deep before I would even go there. ..if that makes sense. So even when I’ve tried to really back off on my own intensity – it is funny what has happened.

    Example – I tried dating someone I knew wasn’t a long-term match – deep down I knew it. I know I want someone with a deeper connection – and this guy and I had fitness in common – our intense workout programs (p90x, insanity) in common & past military experiences –   and that was great in itself. He was also a single parent like myself. I felt nothing deeper with him – and I usually let myself get too deep – even with just kissing – I don’t know how or why or how not to – but it’s like my soul is in just a kiss – very intimate to me and almost too much. So in this situation, after being single so long – I wanted to try something different and I didn’t feel we would have that passion together – and we could actually just have fun and spend time together. It was teetering on the verge of “friends with benefits,” which I have never done and I am the one who said clearly – I didn’t want a serious relationship – just to take this easy and enjoy each other, have fun (saying that was my attempt at protecting myself from past relationships that failed due to too much intensity too quickly). I didn’t want an upfront intensity that past relationships brought – as I would get overwhelmed – panicked and worn out. I would try to set boundaries – guys would say they understood – yet continued on with total 100% intensity – as though they had planned out their future with my and my son and I felt scared by it.

    So in my one attempt to try a different approach, while still having some companionship, etc. I tried to be almost stereotypically “like a man”..sorry if that is wrong or offensive -but tried to have fun without the intensity – no strings attached. I thought this big macho man would be all for it – and he seemed to be fine with it. But, It failed and backfired when we kissed. He had agreed he wanted to just hang out and keep it light.   I am too intense – too revealing – put too much of me – even in kissing – and that is what flipped a switch and he became very intense. He commented on how serious it all became and how he didn’t expect to feel so much..or something along those lines. This intensity – this intimacy – it’s addictive – and hard to go backwards once you get there. It’s hard to explain – but that was my experience. If a guy is just all about kissing madly and not receptive to how I am – not in tune to each other when kissing – then there would be no problem with it. But, I wouldn’t really be into it either! I am making no sense here anymore…it is utterly confusing!

  11. 12

    Okay so I read your article. I found it after searching, no, scouring the internet for “how to go slow” articles. I too hate the shallowness of dating and the whole “keep it light” bull*. It never feels right for me. I read some of the responses on here where some people said “most men don’t want deep, intimate….men want sex, fun, etc…”

    What I have discovered, is the way you “date” and “who” you date, as compared to “who” YOU are, have to be in line.

    For example. You desire to not engage in purposeless light talk, weeks and weeks of aimless texting and “light conversation”, while masking your true feelings, thoughts, and emotions.

    To obtain this objective with a man, you must seek a man who knows what he wants, and what he wants must be what you want. Enter online dating. This becomes most easy with online dating because you can be that candid and say exactly what you want and you will most likely at least meet 1 person who fits.

    Otherwise, strap down for mindless, emotionless conversation that leaves you with that empty and void feeling, longing for a real connection.

    Be sure the guy you seek is comfortable with his TRUTH. What ever that may be. Im sure you know, true intimacy, the kind you and I see, is born from the voluntary and sometimes reactionary revelation of truth. It simultaneously encompasses and embodies trust, vulnerability, compassion, and humanness. Its where real love can grow at its own pace (what ever is comfortable for the two individuals) not at the prescribed pace set by bloggers, overzealous commenters, the media, movies, and society through its cliché’s and double standards.

    Be sure you are sure about the relationship you want (marriage, platonic but emotionally intimate friend, etc.) and just make sure to seek a man seeking the same and capable of the same.

    In this world of confusion, stick to who you are. Makes it easy for those “like you” to find you.

    PS. The speed of a relationships development and sustenance is directly related to the willingness and ultimate sharing of the truth, and each partners ability to understand that truth. The faster the truth is told, the faster the relationship develops. Most people don’t like their truth and prefer to reveal it slowly to assuage their fear of “scaring you off” but if you and your person are comfortable with your truth…OPEN THE GATES!

    Sometimes life brings us floods…and from floods comes new life. Yeah some destruction too. But good things always grow afterwards.

  12. 13

    This is a great article about how to approach dating if you require actual intimacy in a relationship. And it is really in line with deeper dating.

    The piece in the middle about Realness + Attunement = Intimacy is the key. using this works for me in terms of building the kind of relationship quickly where I can learn quickly whether someone is compatible with me as a partner.

    After marrying a man who seemed a good partner to me from following all the old dating rules and learning a decade later that we were never going to grow the kind of intimacy over time that people talk about as the natural progression, I am not willing to play the games any more.

    This article talks about being as real as you know how to be and showing who you really are to you date AND at the same time being attuned to who they are. And you need both.   If you don’t reveal who you are to the best of your ability, and the other person falls in love, they haven’t fallen in love with the real you. And if you aren’t attend to who they are and how they are in any given moment, then you are likely to self-express all over them and scare them off.

    By doing this on every date, I have learned about people so much faster than I would have using my old ways of either being too expressive without being sensitive to the impact I am having or playing the games I think I need to play to get the next date.


  13. 14

    Surely we have to define deep and meaningful here. I’ve never noticed a gender difference as regards the depth or meaningfulness of the conversations I have with people. Perhaps it’s telling that towards the end of your message you mention ‘marriage and children’ as among the things you would like to discuss? I confess I haven’t met many men (Or women) who are usually keen on discussingbthesw topics on a first date:)

Leave a Reply

Your email address will not be published. Required fields are marked *