Photo Credit: Jewish Press

Dear Dating Coach,

I have had the same issue a few times now with boys I have gone out with. They are smart, kind, and interesting, but they seem to lack depth. I really envision myself with someone I can truly communicate with, and I feel like ‘depth’ is a big part of that. They seem to be content to discuss past experiences, current events, and common interests; but not deeper, more thought provoking subjects. Am I looking for too much, or should I keep searching for a deep thinker?


Single Surface


Dear Surface,

Marco Polo was an Italian explorer who we remember today with great regard. I mean he even had an exciting pool game named after him. Pretty impressive, I know. If you’ve ever witnessed the spectacle that is water ‘Marco Polo,’ you know how humorous it is to watch. One person is “it” and they must close their eyes and shout “Marco” while the rest of the swimmers answer “Polo.” Then they must use their CIA spy skills to tag the other swimmers by following the sound of their voices. (I know, it’s shocking that this is not an Olympic sport.) The game usually takes a while, because unless you are playing in a hot tub, it is difficult to tag someone that you cannot see in a pool. So, the poor “it” just continues to say “Marco” pleading for the game to be over, all while praying that someone has forgotten how to swim.



Dating and finding that connection that we need to move forward can be daunting. When you have a specific vision of intense talks and deep conversation, it can be even more complicated. You’ve met wonderful guys, but none that you felt were willing to explore their feelings in the way that you had hoped. You also consider yourself to have depth, so it is natural to want to meet someone that approaches life with a similar lens.


Back Stroke

It is probably important to mention that often shared experiences and the connection that marriage offers encourages a greater depth of communication. Moreover, in frum circles we are only dating for a concise period of time, and one’s “depth” may simply not showcase itself in that timeframe. Finally, chemistry often breeds depth, allowing us to connect in a deeper and more meaningful way. If compatibility is there in all other aspects, such as shared hashkafa, smarts, empathy, respect, and a shared vision for the future, then his willingness to have more meaningful communication may only be a matter of time.



There are certainly guys with depth, guys that want to explore the “why” versus only discussing the “what.” Only you can know how vital this is to you and to your future marriage. I can encourage you however, to remember that good middos, chemistry, and compatibility should always take center stage. Perhaps you won’t meet a guy who wants to have existential conversations, but someone with character and mentchlichkeit will be happy to listen to you as you explore life’s burning questions. Maybe he won’t share the same need to “go deep,” but his willingness to listen will certainly make him a wonderful partner and husband. Certainly, deserving of a chance; encouraging you to open your eyes to the real possibilities available to you in the depths of the dating pool.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.