| Match Quest |

What’s Really Holding You Back?

I’d also like to suggest a deeper dynamic that may be holding you back from being honest



ecently, I’ve been dating a boy who I’ve come to really respect and admire. We’ve discussed many different topics and have found each other to be on the same page hashkafically. An engagement isn’t imminent, but it’s clear to both of us that things are serious.

One thing that brings us together is the similarities between our families. We both have parents in chinuch, and our lifestyles are simple. It’s clear to me that this boy appreciates such a lifestyle and puts no value on material things. I cannot say the same thing about myself. Although I’m not obsessive by any means, I definitely have an attraction to nicer and more expensive items. Although my parents don’t support it, I use my own savings to purchase the latest style clothing as well as designer shoes and accessories.

Now I feel stumped. Do I have an obligation to reveal this tendency of mine to the boy when I know he will clearly not appreciate it? I’m afraid that if he knows, he’ll drop the shidduch altogether, as it goes against his whole mehus (being). Is it better that I leave it unmentioned and wait until after we are married for him to realize on his own?

But I always learned that the most important thing between a couple is trust. By withholding this information, am I asking for trouble and starting the relationship on the wrong foot?


Dear Confused,

If I had to rename you, I’d change your signature from “confused” to “conflicted.” It actually sounds like you know the answer to this question, and are looking for validation rather than clarity. You know what you need to do; you’re just afraid to do it.

Yes, trust is the foundation of any solid relationship. I believe we’ve seen too many examples of failed young marriages because one party did not deal truthfully. And since you ask the question, my guess is that it’s already niggling at you.

How will you feel about yourself if you get engaged and feel like you misled or “trapped” this person you hold highly of? How will it play out in a marriage if you’re hoping for nice things, and he feels like he never signed on for that? The potential for deep disappointment on both ends is tangible. There’s so much about this that feels like a setup for disaster.

There will always be issues a couple doesn’t see eye to eye on. That is the nature of marriage and Hashem designed it that way to stretch each partner. Discussing this issue in advance will give you experience in real time in seeing how the two of you are able to resolve differences of opinion. It can be very telling and something you probably want to know in advance.

An issue like this doesn’t have to be a deal breaker. There are plenty of ways to compromise or to accommodate both needs here. If it becomes a deal breaker, this may be a sign of other dynamics at play, which can only be good to know about before you get engaged.

I’d also like to suggest a deeper dynamic that may be holding you back from being honest. Are you perhaps ashamed of your wishes? In our world, poverty is often glamorized and austerity glorified. I’m not here to comment on the trend, only to point it out. If you subscribe to this narrative, there’s a part of you that you may be ashamed of.

Vulnerability dictates that we allow the other person to see us, even the parts we might be ashamed of, and to accept us. That doesn’t mean we don’t have to continually work on ourselves and grow. But it does mean that we have a healthy acceptance of ourselves where we’re at, knowing that as growing beings, we always have work to do, but that we, essentially, are okay.

That sense of being okay is an integral part of emotional health and contributes greatly to a healthy marriage. Ask yourself if that piece is in place. Or is that what’s really holding you back? Because if it is, not saying anything will eventually backfire beyond his feelings of being misled and possibly betrayed. You may end up feeling marginalized if there is an important part of you that never gets a voice.

One last point: It’s significant that you think he doesn’t know that you like nice things. I’m assuming you’re wearing some of those nice things on your dates. Even if he’s not familiar with the specific designers and trends, I assume you’re giving off a polished vibe. Where is the general conversation about materialism in your hashkafic discussions? Whether he is completely clueless, or (subconsciously?) avoiding it, you want to know that the two of you’re capable of addressing important issues together in an adult fashion. It’s not just about getting engaged. It’s about the ability to have a healthy, functional, meaningful marriage.

May Hashem help you find the path to your bashert with integrity while staying true to yourself!

All the best,



Sara Eisemann, LMSW, ACSW, is a licensed social worker and a dating mentor. She lectures on topics related to relationships, personal development, authenticity, and growth. She welcomes questions, comments, feedback, and interaction at matchquest@mishpacha.com

(Originally featured in Family First, Issue 675)

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