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Relationships Advice: Missing A Lost Love

Dear Rabbi Bernath,

I dated Brandon for a while. After a month in Israel, I came back and was scared to speak to him. I was afraid of being rejected. I froze up.

Not knowing if he wanted to marry me was getting frustrating. I didn’t want another misleading relationship. My rabbi said to present an ultimatum: ask Brandon if he wants to marry me.

So I did. His reply: “I want to say yes, but I’m going to say no.”

I understand why he said no. After not seeing me for a month, our relationship needed a reboot, not an ultimatum. I feel like a fool for following this rabbi’s direction, instead of following my heart.

Three months later — zero contact. I still miss him, love him and can see a life with him.

Maybe I’m going crazy. I’m not sure. But a part of me is still hopeful.

My rabbi told me to not seek any contact with him whatsoever. But I’m afraid I am only following that advice out of guilt. But it’s not what I really want — I want Brandon to want me back.

I’m also scared of being vulnerable by being the one who is chasing him. It feels extremely degrading, as a woman.

What do you think I should I do?


Dear Olivia,

I feel your pain. There are so many emotions you must be dealing with, some of them complete opposites of each other. Dating can be a very confusing time of life. As a matter of fact, the greatest blessing you can give to a friend who’s dating is, “May you have clarity.”

There are two points in your story that I think we should clarify: a) how to best use rabbis and other coaches when you’re deep in a relationship; and b) what to do now.

To summarize: you froze up, followed your rabbi’s advice and now you regret it.

I think that your rabbi intended something good: he was trying to get you to cut it off with Brandon. He intuited that Brandon would say no to your ultimatum and thusly set you free.

But you’re not free yet, are you? You still don’t know what Brandon really thinks and the uncertainty has you stuck. And you can’t even contact him to figure it out, as your rabbi is trying to keep you safe.

At the beginning of a relationship — be it a formal shidduch, or modern Western dating — things tend to be pretty stock. There are fairly standard things that happen and there’s no emotional depth to the relationship yet. A coach’s advice at this stage can be followed pretty confidently.

But when things get deeper and more emotional, the role of the coach changes. At this point, there’s nobody who knows your relationship, and your emotions, better than you. If you don’t understand exactly what you’re doing, then don’t do it. Ask questions until you’re clear on what’s going on and make the final decision together with your coach.

My advice, in retrospect, would have been to communicate with Brandon about how you feel and then ask him to be honest with you, too. I know that some people are like a closed book, and confronting such a person could make you feel vulnerable, which sucks. But it’s the only way to find out the truth about how Brandon really feels about you.

As a relationship progresses, there comes a moment when two people are honest with each other about their feelings. In the movies, this is called the “I love you” moment. In real life, and especially in a shidduch, it could sound very different. Sometimes, it’s even, “I don’t really love you.” But at least you have clarity.

I don’t believe that Brandon loves you, or that a reboot can save your relationship. And it’s degrading for you to give chase.

But if you want to know for sure, communicate with your rabbi about how you feel right now. Ask him to call Brandon for you, tell Brandon what’s going on and find out what his true feelings are — for your sake. Brandon may be more open if he’s not speaking directly to you.

And may you always find clarity, and communicate it with confidence.

Rabbi Yisroel Bernath

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