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

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!

Ready for Lasting Love?
Ready for Lasting Love?


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.