Freezing Up

By | September 9, 2015


I’ve been dating for a year and have been learning a lot from each of my experiences. One of

my weak points while I’m dating is not asking enough important questions. I find myself

freezing up when I try to think of how to word my questions because I don’t want to put the

boy on the spot. I see how this is detrimental since I end up going out with each boy longer

than I would need to.  If I could be more upfront in the beginning about what is important to

me, we probably would both have more clarity. Otherwise I am  a confident dater who keeps up

conversation well and answers the questions posed to me. I was wondering if you could help

me put some important dating questions into words so I can feel confident that these are okay

to ask in the future. Specifically, I would like to know how to ask a boy how important his

Yiddishkeit is to him and how he plans to raise his future family.

Thank you so much for all the incredible advice


Your question reminded me of an old favorite dating joke. A young man who was starting to

date asked his older brother for advice on topics to discuss on dates. The brother replied, “The

three “F’s”- food, family and ‘filosophy.” Armed with this knowledge the young man asked his

shy date, “So, do you like lokshen kugel?”, to which she shook her head no. Ok, on to family.

“Do you have any brothers?”. Once again, she shook her head in the negative. Racking his brain

to stir up some conversation he turned to philosophy. “If you had brothers, would they like

lokshen kugel?”

I love this story because it underscores the futility of using canned lines on a date at the same

time that it captures the inherent dilemma of trying to know a stranger deeply in the unnatural

context of a shidduch date. I would love to give you some great lines and take care of this

problem for you, but that won’t work. Using someone else’s words will feel and come off as


The first thing you need to remember is that we get information from many sources; direct

questions are but one way. You will learn much about how important a boy’s Yiddishkeit is to

him by the things he tells you, by the priorities he sets etc.  For example, if he smugly tells you

about the Walmart gemach, where he and his friends bought an air conditioner at the

beginning of bein hazmanim and then returned it at the end of the season, reveling in his

ingenuity all the while, he has told you a lot about his integrity (or lack thereof).  Alternatively,

if he mentions in passing how they couldn’t start their trip at 7 p.m. because that would mean

missing Mincha, he’s told you about his commitment to davening and Avodas Hashem. So you

need to read between the lines. Asking a direct question may just give you an answer he thinks

you want to hear.


Most of what you’re listening for is not actual information but attitudes. When does he light

up? Does he get excited when he’s telling you things related to his Yiddishkeit? Those are the

moments you want to step in. If he shares an anecdote or a feeling about his Yiddishkeit, stay

there. Ask him to tell you more. See where the conversation goes from there. As much as you’d

like to know sooner rather than later, this is a process that has to unfold. Coming across too

pushy will be a real turn off.


This will also help with your feelings of freezing up. If you allow the conversation to unfold

naturally you won’t feel as stressed about coming up with the perfect wording for the

question.  As you focus more on listening to what he’s saying and less on what you’re going to

ask, you will know more about him AND your date will feel heard and well received. As the

relationship progresses you will have to gauge when it is appropriate to ask questions like,

“Where do you see yourself in five years?” which are both personal and generic at the same

time. When your date tells stories about siblings or mentors he is close to, you can ask what it

is about them that he respects. There are wonderful games designed to help people know each

other better and playing them can be a way to deepen your knowledge of each other in a safe,

less pressured way.

Don’t be so hard on yourself. The entire onus of this process should not fall on you. Hopefully

at some point your date will be initiating some of those questions as well. Focus more on being

present in the moment and less on trying to control the process.  



Category: Advice and Chizuk

About sara

Sara Eisemann, LMSW, ACSW, is a therapist who lives in Oak Park, Michigan, with her husband and five children. She is on temporary leave from the field (about 10 years now) as she raises her family, but has maintained her love for working with people. Sara lectures on topics related to relationships, personal development and growth. She has a passion for humor, writing, and kiruv but mostly for promoting self-awareness and authenticity in our relationship with Hashem and with each other. She welcomes questions, comments, feedbacks and interaction.

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