Dating: Let Us Trust Ourselves

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I was on my way home from work last week when my friend Ayala called. “I need to vent. I went on a date last night.”

Before she could continue, I already knew I’d be able to commiserate. While it’s a necessary path to finding one’s life partner, being in the “parsha” is no fun. For many of us, it’s a series of lousy dates interspersed with enjoyable moments, and high hopes crushed by incompatibility or unexpected rejections, all on a running basis and in no particular order.

“I actually like this guy,” she continued, “but he said no to a second date. I spent all night psychoanalyzing everything I said and did, and the only thing I could come up with is that he’s not attracted to me.”

This led us down the rabbit hole of verbalizing every possible flaw that could be found within the shidduch dating system starting with the acute focus on size, leading to the unrealistic standards and expectations that guys have, and finally how frustrating it is to finally meet a guy you like who doesn’t properly give you a chance for one seemingly insignificant reason or another.

I’ve struggled with being fat within a society that values thinness. I’ve vented many a time about the rejection I’ve faced due to my size, and the comments I’ve received from shadchanim and family alike about the prospects I’d have if I’d only lose a few pounds.

However, there is no one thing that results in a person feeling like the system is working against her. We each have our battle to fight and while mine may be destigmatizing my weight, another may find herself not being set up due to her mental illness, or her tall height, or her lack of book smarts.

If we’d take a step back and look at this bigger picture, it would be unfair to say that any one of these things is the issue with the system. So I suggested to Ayala that we push the conversation further to see whether we could pinpoint what exactly the issue here is.

The more we compared experiences and frustrations, the more we realized that essentially we feel like the messages we’ve been given are leading us to feel like we should just settle for what we can get.

“You know, after something like that happens, it kind of makes me question myself. I know what I want, and I know what I deserve… but maybe I’m wrong. Maybe I don’t have that awesome a personality, or I’m really not that attractive.” When Ayala said that to me, I felt a little tug in the area of my heart, because it resonated with me. With every rejection comes a blow to our confidence, and with enough blows, we begin to grow wary. We’re emotional human beings, and logical or not, we sometimes find that we begin to wonder whether we’re wrong about ourselves.

For years I dated with the intention of proving myself to my date. I’d hope that I gave the right answers, and expressed myself the way I thought he’d expect. If we ever disagreed on something or had different approaches to a hashkafic concept, I found myself subtly adding a “disclaimer” to my responses, as if to let him know I was open to compromise, and could potentially do things “his way.”

It wasn’t until I was twenty-five that a friend pointed out to me that my first course of action when going out with a potential suitor should be to determine whether I like him. That I should consider whether he’d be a good fit for me as a husband, my children’s father, and a life partner. My mission was to establish whether or not this was a man I wanted in my life for the rest of my life, not whether I could be the woman he wanted me to be.

It seems so obvious when I say it now, but it wasn’t then. And in speaking with many friends, I’m not the only one who took this initial approach.

I believe that part of the reason so many of us fall into this trap is because it’s hard to stay true to yourself and remind yourself that settling is not an option when the voices around you are constantly telling you to “stop being so picky.” As if wanting to find the man who will complement me best, is not OK.

What I’d like to ask is, why is being picky such a bad thing? Like I said previously, this is someone I plan to live with for the rest of my life. Shouldn’t I be picky?

Shira, a close friend of mine, got married at twenty and divorced four months later. She and her ex-husband had gone out on six dates and she was completely surprised when he asked her to marry him.

“You have to understand,” Shira explained, “this was the first guy who actually said yes to me. I was twenty and hadn’t gone out before. My family dynamics aren’t simple, and I didn’t think anyone else would ever be interested, so I didn’t object.”

She went on to explain that she had been encouraged to continue dating him despite questions and doubts. When she asked her mentors about her lack of feelings towards him, she was told that would grow after marriage. When she shared concerns about his character, she was prompted to consider what a blessing it was that a “great guy from a great family” was dating her considering the circumstances. It seemed that everything was so right, she assumed she must be the one feeling wrong, and without proper guidance, she lacked the ability to properly express what exactly was bothering her.

It would be imprudent not to mention the pressure that comes in the form of shadchanim, family members, and sometimes even rabbis and mentors. The external voices that push young adults to take the next step, to get engaged, and figure the rest out as it comes. There can be negative consequences to this dynamic.

With every piece of advice that a girl gets along these lines, without being heard out, without being validated, her own intuition gets pushed deeper into the abyss of doubt. It’s no wonder we’re left with many young women who are second-guessing themselves.

Word on the street is that there are a lot of guys out there who are offered “lists” of women to date. It seems like that approach gives them the space to figure out who and what they want. But what I can say is that girls are experiencing something very different. For many, the approach can be “I’ll take what I can get.”

We have these conflicting emotions going on inside of us. On the one hand, we know we deserve better. We know that finding the guy we intend to spend the rest of our lives with is no small feat, and is one that requires we “be picky.” On the other hand, rejection takes its toll. There are only so many times one can get a no before they start to second-guess their own voices. Throw in an external voice of pressure insisting that the time is right for them to get married, and you have a sure case of settling on your hands.

I’m really grateful that I didn’t experience the kind of pressure that so many others do. But, even without that, I made mistakes. I dated people I shouldn’t have, I agreed to many more dates that I should have, and I said no for others before even giving them a chance to say yes to me.

Have you ever seen a man and thought to yourself, “That’s the kind of guy of I’d like to date, but the kind of guy I’ll never get?” I have. It’s my reality, and it’s a real pity because that’s not my nature, it is a learned message.

I’m not proposing a solution to this issue or blaming any one party, but I’d like to make a request of you: Stop telling us we’re too picky. Stop blaming us for being single. Stop pushing us to date someone we’re not interested in dating. And stop pressuring us to get married to the wrong man.

Here’s what you can do instead: Start listening when we tell you about ourselves and what we’re looking for. Start making suggestions that align with what you already discovered about our character, values, and goals. Start respecting us and involving us in the community for who we are as single women. And start telling us that it’s OK to trust our own judgment.


Sara Kupfer, founder of Fit Jewess, is a fitness coach with the mission of empowering Jewish women worldwide through joyful movement and fostering a community united through body positive and weight neutral fitness. She is a CrossFit L1 trainer and HAES advocate, and encourages her clients, both in person and online, to view exercise as a way to feel more confident by increasing energy, gaining strength and discovering how amazingly capable their bodies are. Check out her website at and her instagram at @fitjewess