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Where I Messed Up at The Singles Shabbat: Letters of a Single Man

3/27/2025

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by David Kilimnick

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See the guy passing the food and not eating it. He has a chance at meeting somebody. There is no way to eat Chumus that will attract a lady. (Photo: Moishe House in NY Times)
Dear Dave,
I did good at the singles weekend. I met some women, got phone numbers, and they rejected me by phone. But I made some mistakes on the weekend. And naturally, some of this stuff will hurt your game and bring you down.
I made rookie mistakes. When you've been single for as long as me, you should know how to work a Shabbaton. You should know how to strut your suit and Shabbis walking shoes.
This is what I did and why some stuff doesn't work out. If you have any advice, please let me know. It won't hurt more than the girl calling me a creep.
 
I Met Her Too Soon
I met a girl in the beginning of the weekend. At that point, I knew I had no chance. I only have fifteen minutes of game. There were two more days after that. That's forty-eight hours. I can't hold attraction for forty-eight hours. I had already run out of questions about where she grew up and what she does for a living. What do you do after that?
I turned into a stalker real fast. Real fast when they don't want to talk to you. The whole Shabbaton she's now asking, "Why is this guy still here. Why is this guy following me to all these programs."
By Saturday morning, after saying "shalom" for the eighth time, I was now creepy. Romantic turned creepy. By the time Sunday rolled around, she'd met a dozen girls I've dated, and they confirmed I was creepy.

Too Much Energy
I gave so much positive energy. Too much in the beginning.
Goes great for fifteen minutes and then she finds out I've run out of questions about where she's from. Twenty minutes later she hears I'm a rabbi who does comedy. Now, I have no chance. And my material on being single does not help the stalker cause. Especially the stuff about the date that went bad, when I started knocking on her door and her parents said they were going to call the police if I show anymore affection.
I should've left the Shabbaton right after we met. I should've kissed the three-hundred-fifty-dollars goodbye. I would've had a chance if she never saw me again.
I have to get good at not putting out any energy. Just got to sit there, not talk and look cool with my Yarmulke covering my bald head.

I Ate
I can't eat at these things. I'm disgusting. The amount I eat, that will turn off any girl. Guys are disgusted by me.
I focus on food. When I see food, I devour. It's a gorging process done with hands. And it was good food. Which meant I went up five times. The girls know I went up five times. They're counting. They're trying to figure out if there's a reason I'm not buttoning the double-breasted suit. Wearing a double-breasted suit and trying to date girls under sixty is another rookie mistake.
I get involved with food. I see it and I lose myself in it. If you looked up for a second, you would've noticed the look of the girl trying to figure out why this guy is eating steak with his hands licking his fingers at a single weekend.
I put on 20lbs by Saturday morning. Worst time to have a singles event. Food around and it's over for me. A woman should never know I eat. I should go on these things and starve. My two-hundred-thirty-pounds should be an anomaly. They should be asking how this guy got so heavy without eating. At least they wouldn't see me walking around with choolante grease on my shirt Saturday afternoon.

You end up hitting yourself for this stuff. Next time, I'm not making any moves till I'm out of there. I'm going to show up, not eat, not talk. I'm going to leave before any of the girls talk to me and I'm going to go hungry. That's my only chance of meeting a woman and making it happen. And I'm wearing a husky single-breasted suit. And I'm not going to tell the girls it's a husky suit. Girls are not attracted to husky.

If any girls do talk to me, I'm pulling out a timer. Fifteen minutes and I'm out. I see her at another event, there will be no hellos. Unless if I'm at the fourteen minute mark and I have another minute of game in me.
I think I'm ready to meet my Bashert now.
LSimchas,
David
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