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Dating Advice: Love is accepting each other’s shadow

How well should I know someone before deciding to “get serious” or get engaged to them? Will there be a sign when I know them well enough?

Thanks for this question. I find it deceptively simple — there’s a lot to unpack in a tiny question.

First of all, you’re assuming that “knowing the other person” is the measure of your relationship. I’m pointing that out, not because it’s a bad assumption, but because it’s a bit unusual… maybe in a good way!

Most people would be asking, “When do I know I’m in love?” They’d assume that some sort of emotional state is the prerequisite to be “ready.” And in a sense, they’d be right.

But according to Hasidic philosophy — with a few notable exceptions — an emotion is positive only when it’s born of the mind. In other words, if you have an inexplicable emotional bond with someone — you love them without really knowing them — then you might be infatuated, and that’s not good for the long term.

Infatuation means that you’re in love with who you imagine the other person to be. But one day, maybe even 10 or 20 years later, you’ll wake up to the fact that they’re not the person you imagined. This pretending, if it happens, is usually mutual. As a matter of fact, you might even be imagining who you are, or allowing their (false) image of you to define who you are.

True love comes from knowing the other person, and them knowing you. So how much knowledge is enough?

Before I answer that directly, I’ll take the opportunity to emphasize something that you’ve brought up: dating is not (just) having a good time. That’s how it starts, and it’s super-important to have a good time together. But dating progresses by getting to know the other person, and that means having solid conversations about yourselves.

I feel like most people, once they’ve gotten past the “we enjoy each other’s company” phase, move directly into a closer relationship, or maybe it even gets physical. This is a mistake, because it circumvents the process of you actually having a serious conversation together. What is their philosophy towards life? What do they believe in? What do they value? Some married couples I meet can barely answer these questions about each other — that’s not a good sign.

But if you focus on having these conversations — and if you both know yourselves well, and you’re both honest — you may only need five, 10 or 20 hours of purposeful conversation. That’s all it takes.

So that’s what’s behind your question — your presupposition — and that’s a lot. I wanted to point it all out for everyone reading.

OK, I’ll get to the actual answer now … finally.

Recently, during a relationships seminar, somebody asked a therapist whom I respect a lot, “What is love?”

(The room did break out into song at that point — but I digress.)

His answer fascinated me: “Love is freedom.”

Love is when you can express the parts of yourself that are normally hidden — your shadow — and the other person does the same … and you still accept each other.

So it’s not a certain amount of knowledge that gets transferred in those 10 or 20 hours of serious conversation. At the end of the day, it takes a lifetime to get to know another person. As the venerable love researcher John Gottman famously concluded, curiosity is the key to a long marriage. You don’t want to know everything.

It’s a process, not a product, that needs to be proven. Are you comfortable showing your shadow to the one sitting across from you? Is the feeling mutual?

If you do it once or twice and they like it and want more, that’s a good sign. I would even argue it’s enough. You have a lifetime to learn the rest of who they are. And hopefully, even then, they’ll still find ways to surprise you.

Looking for dating advice or have a question for Rabbi Bernath? Email him at

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