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Singles Weekends Will Bring You Down: Letters of a Single Man

3/20/2025

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by David Kilimnick

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Looks good. But just wait till she doesn't like him because she saw him eat Chumus. Chumus kills relationships. (Photo: Moishe House in NY Times)
Shalom Dave,
Singles weekends will bring you down. Especially Jewish ones. I just went on a Shabbaton. A Shabbaton is a weekend event over Shabbat where you know you will only meet people that like Shabbat, due to the lack of live music. You show up, meet people and eat. Shabbatons are singles events where singles are focused on food.
It was nice. I had a good time. I met some good women, got their numbers, got back home and got reject me by phone. But right after the Shabbaton, I felt this great flood of depression running over me for the first time. One that said, "I'm still single. I had just been around so many Jewish singles, and I am still single." And I understood.
Let me be clear. I was down. I wasn't depressed. I don't want this letter being used as proof of a psychological disorder. That will not help the dating prospects any more than being a comedian.
This is what I think brought on the deluge of depression deluge. And I'm a guy. Please tell me if I'm off. I shall break it down. This is why single people walk away from these things depressed.

Two Thousand Singles
There were two thousand singles present over the course of the Shabbaton. With so many singles, I felt like I'd been rejected by the Jewish nation. At the end of the weekend, it hit me that the whole of my people had turned me down.
I met women, but it still made no difference. When there are over a thousand women that are not Matim, not fitting to be your Bashert, in one place, you get the full feeling that your people has rejected you.
When applying, I got rejected by less colleges. There's something to a dating application process.
Over two thousand and not one of them is your spouse. What do you do at that point? Do you move to Israel? Do you retire? Who do you talk to? Gd?


Single People Look Depressed
I kept up the positive energy, but it's tough around Jewish singles who only want to get married, and don't want to meet a guy.
Video adds twenty pounds. Seeing other singles adds twenty levels of depression, and twenty pounds. You see these other singles and you start to see how bad your life is, in front of you. And you start to see these older guys who got heavier. You see that single guy and you start thinking, "Am I like that? Am I over forty and single?!" Women are thinking, "Am I stuck with that guy? Has my life come to this?! Am I dating my dad?! Do all guys get fatter?!"

Didn't Find the Right One Again
That's a realization that hits me when I was driving home. That and dinner. After eating all that food at the Shabbaton, I'd realized I was hungry again.
I met some women. I'm a man, I've got moves like, "Where are you from?" That's my go to pickup line. They always have an answer to that. I don't like to take chances.
Some of my friends didn't meet anybody. Nobody for them to call, to get rejected by phone. And I feel bad for them. Nobody to DM on Instagram, who now sees your picture in the light, to reject you through text. It's a waste of time if you come away from a singles weekend without a woman telling you, "I have a friend that might be good for you."
How many more places do you have to look?! And this weekend was in Florida. Your future creeps up on you real fast down there. You see the ninety year old singles and that brings on a different level of depression. Another fifteen levels. You go on those Shabbatons and they don't even have Instagram messenger to reject you.


I'm Broke
Leaving the Shabbaton, I realized I'm out of money.
I don't know the connection between Shabbatons and inflation, but it's there. The economy has influenced our dating. Interest has affected singles event prices.
I can't afford these events anymore. But I have to go. Otherwise the women know I'm poor. If you can't afford the event, the women know you won't be able to afford Jewish day school.
They can cost up to three hundred fifty dollars. Then, there's the hotels, the flights, the car rental, the dinners. I'm out four thousand dollars. I met the girls, but I can't afford to take them out. I have to wait till May to pay off the debt.
There's got to be a charitable individual out there who doesn't care about poor people. They should be able to fund this. Free would be good. Single people would feel better if they met nobody for free.
But we got food. For three hundred fifty dollars, you want to eat as much as possible. That's why we focus on food.

Speeches
And this hit me at the end. They had speakers reminding us about the fact that we're single.
If you're not down enough. If you haven't lost enough money. If you haven't gone out of your way enough to let people know you're desperate. If you haven't been rejected by over a thousand singles yet. They give a speech about how you messed up.
To spiritually uplift you, they bring in the Kabbalah to let you know that you're single because Gd also doesn't love you astrologically. Your zodiac precludes you from love since the day you were born.
Each speech ends with a practical teaching that you have no hope and you have to go for somebody you don't find attractive. Married people are allowed to be attracted to their spouse, but you have to get married because you're a loser. That's in the Zohar somewhere.
Listening to the speeches, it didn't hit me at the time. Afterwards, I was thinking, "I really did mess up. I definitely went wrong somewhere if I have to listen to this."

People Are Looking
It's a heightened sense of awareness of your being alone at thirty five, forty five, fifty five, ninety five. Truth is, I have no idea what the age of some of those people at the Shabbaton is. When you leave the event and you're all alone again, and broke, the drawing board becomes smaller.
If people went to these events to just enjoy a four thousand dollar weekend, they would walk away happier. Maybe not. The four thousand dollars does hit you. After the weekend. After the high from the energy of the event is over, it hits you. You're broke and you're older.

Those are some of the reasons why people get down on themselves after these weekends. But there is no greater reason than spending all that money to get rejected by the nation. By all of your brethren. I showed up to shul the following Shabbat. I was shocked when they gave me an Aliyah to the Torah. I thought the people didn't want me.
With all that rejection and depression, I'm going to another singles event next weekend. I already paid three hundred fifty dollars to get rejected by another of our tribes that was not in Florida. Maybe they'll have a guest speaker to let us know why we were rejected by the Persian community as well.
At least I ate a lot. I walked away heavier. It might just be the extra pounds bringing me down.

I hope that explains why single people don't like going to singles weekends all the time. Dave. This is why single people like going to couples retreats.
LSimchas,
David
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