| Match Quest |

“I Can’t Take Any More First Dates”

“How do you feel about doing the first date or two on Zoom?”


I’m curious to hear your opinion on this matter. I’m a 28-year-old male who over the last seven years has dated more women than I care to count. To say I’m burnt out would be the understatement of the year. I still very much want to get married, but I could do without the whole dating thing. So here’s my question. How do you feel about doing the first date or two on Zoom? I know it’s not ideal, but the prospect of getting dressed up, fighting traffic, paying tons of money, and looking for parking is sometimes enough to get me to say no, unless the suggestion is very compelling. I feel like this would be such an efficient way to weed out the dates that would end up being one and done. What do you think?
So Done


Dear So Done,

I hear you, man. You sound exhausted from what you’ve been through. I have to imagine that seven years in, you’ve probably had some really draining experiences. Even when things go smoothly, your description of what every date entails paints a clear picture of the heavy investment and certainly helps to clarify how frustrating it is when the date goes absolutely nowhere.

You describe a more efficient system that doesn’t require such investment, but, you see, therein lies the problem. This isn’t a business transaction, this is an encounter. And the goal isn’t efficiency, it’s connection. The investment is precisely what is needed to build connection.

Another scenario that is the same but totally different is the coffee date. While a coffee date is different in that the couple is meeting in person, it shares the same quality of less investment. Why should we go to all the trouble of getting dressed up and sitting in an awkward lobby talking about the seminary or yeshivah we went to ten years ago when one cup of Joe might instantly reveal that we’re not meant to be?

It’s a solid question. I get it. I get the burnout. I get the vulnerability each date represents, even though we’re acting all nonchalant about it. I get that each time we go out we take a little piece of our soul with us. And I get that sometimes it just all feels like it’s too much.

And at the same time, this is what relationship is about. It’s about bringing your whole self into it. As Rav Dessler explains in the Kuntres Hachesed of Michtav MeEliyahu, the more we invest in something, the more we love it. Or as they say much less eloquently in the vernacular, “No pain, no gain.” The more we give of ourselves, the more we see a piece of ourselves in that person, and so we feel connected and identified.

And this is probably why you don’t want to invest any more of yourself — you’ve already given away so many pieces.

The reality of relationships is that they do require vulnerability and investment to progress. Two people on a coffee date or a Zoom date are basically wearing signs that say “I’m not all in” without ever saying a word. How does that breed connection? Vulnerability by definition requires safety, and who would be willing to risk anything when the environment is so guarded to begin with?

Obviously all of this is occurring on a subconscious level, but as we know, that type of communication is far more powerful than verbal communication.

Having said all that, I understand there are times when Zoom is a blessing. If there is no way the couple can meet logistically, and they want to have a short date just to kick-start the process, I can see certain scenarios where that would be helpful. Sometimes long-distance dating logistics are such that there’s a long time between dates, and a supplemental Zoom date is helpful to keep the flow going. And sometimes you really are too exhausted, and all you can muster is the energy for a coffee date, so that’s all you do.

I think the point is not to give an all-or-nothing answer, but to recognize the cost of not meeting in person. We need to appreciate that showing up with your full self, as hard as it is, gives the relationship its best shot. And it sets the ideal tone for what will iy”H become the foundation of a lifelong relationship.

May it come quickly!

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 862)

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