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Mistake of Sitting with Guys at The Singles Weekend: Letters of a Single Man

4/2/2025

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by David Kilimnick

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Focusing on food is smart. This way you don’t end up talking to the girls and saying something stupid. (Photo: Moishe House in NY Times)
Dear Dave,
Come to think of it, I made a lot more mistakes. Last time, I told you about the girl I talked to for more than five minutes, ruining any chance I had with her, and the fact that I ate. Which was a total foolish thing to do. But I couldn't control myself around brisket.
I've been writing you a lot lately. But I need to get these thoughts off my chest and onto somebody else. Thank you for being that guy. I need to work through them somewhere. Need your feedback buddy. I think I'm hanging out with the wrong people at these singles Shabbatons.
 
Here's where the mistake started. I sat with guys. My biggest mistake of the weekend. Sitting with guys will bring you down. Kill your game. Once I sat at the guy table the good energy vibes was gone. It was guys I was sitting with. The weekend was downhill from there.
Nobody wants to be around guys. They are depressing. But after thirty-six hours at the Shabbaton, asking girls where they come from, guys were the only ones willing to talk to me. Maybe I have to come up with more questions, like "what are your hobbies." Girls like that.
It brought me down. Sitting with single guys will bring anybody down. Especially when it's the guys who gave up. I noticed guys coming over. It was a pattern. A guy sees a girl, walks over to her, other guy starts talking to her, he has nowhere to go, he sees the guy table, he comes to the guy table, tries to start a conversation, nobody responds, he takes a seat, understands the weekend didn't work out, looks around, notices food, gets more of it, comes back, stains his shirt, stays at guy table.

They were all trying to look cool. Sitting with a bunch of dudes who had been rejected, looking cool. It takes a lot of self-belief to pull that. Strategizing. Each one was trying to figure out how to make their way out of the guy table, trying to figure out how to make the move they forgot to make fifteen years ago.
It's a messed-up conversation where the word "so" pops up every half minute. You sit there with these guys scoping the room while licking the T-bone and your hands, saying "so" and looking cool by not talking to women. After a half hour of "so," I am walking around believing my future is relegated to these guys that haven't had a conversation since they saw Chana Leah across the room fifteen years ago.
The only positive here is that I've made some guy friends over the years of Shabbaton attendance. I see the same guys at each of the events. All now seventy years of age. At least the seventy-year-olds know how to enjoy their food.
I'm beginning to think these Shabbatons don't work for everybody.

Then I saw guys from camp. I have to stay away from these people. So many people I don't like. Why people become counselors when they can get a job mowing lawns for the summer still baffles me. Why do I need to see my past everywhere I go?
I don't need my past creeping up on me like that. I don't need memories of my underwear on a flagpole when I'm courting a woman. If I'm going to meet a woman, it needs to be information from within the past three months, that I've been working on myself.
Is the only way out to convert? Do I have to go to Muslim Mixers? If I converted, I might get stoned, but Jewish girls would like me. The problem is America. I see these people in America. I've got to run away from these camp people. It's Israel. I've got to get back to Israel to get away from Jews.

Then I went back to conversing with women. I shouldn't have done that. That's how you kill a singles weekend. I should never share my thoughts around the opposite sex. Not a good idea. My thoughts as a guy will kill any chance at relationship.
The guys at the table killed all my vibes. I started sharing my real thoughts. She doesn't need to know my thoughts on marriage and where to send the kids to school, until I meet her mother and her mother tells us what we're going to do. If we send the kids to Jewish day school, her parents will be paying. I shouldn't have mentioned that part either. But sitting with the guys messed me up.
They ask questions. That's a trick. They don't want answers. Though she asked about camp, the underwear on the flagpole story was not a good idea.
And then I said I thought she was cute. Stupid. Never tell a girl you're attracted to her. They want guys who are not into them.
A woman should not know I have thoughts until marriage. One day, when I come home, I'll let her know I want to hang out with guys. Get some smokehouse and look cool. But I won't tell her that till marriage. Otherwise, there is no chance we're getting married.
You're married Dave. Did you talk to your wife before you got married?

Next time I go to a social event, I'm staying away from people.
From now on, I'm only going to singles weekends where there are no girls I've dated. They know about me. And no modern orthodox Jews from New York. I don't need my past following me everywhere go. I'm also staying away from elementary school friends. I did some crazy stuff in second grade. I don't need a pencil up my nose keeping me from my Bashert again.
LSimchas,
David
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