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The Guy No Woman Should Date

Ironically, just hours before Lag Ba’Omer, the day we commemorate the students of Rabbi Akiva dying because they failed to show proper respect for one another, I experienced one of the most disturbing conversations I’ve had in over 25 years as a matchmaker. I had never met “Moshe.” Someone had suggested him to a woman…

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From Erev Shabbos Chaos to Shidduch Clarity

We all know that friend or relative whose Shabbos table is already set on Thursday night. The food is prepared, the house is spotless, and everything seems calm and perfectly organized. I love that version of reality. But somehow, in many homes, it doesn’t work out that way. Five extra guests call at the last…

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Was Queen Esther Old and Ugly?

Coming out of the Purim holiday, I read an opinion that Queen Esther, before she married Achashveirosh, was at least 40 years old. According to some commentaries, from her yellow skin tone to other ugly features, she may not have been a beauty queen. We will come back to this point in a moment, but…

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A Purim Reality Check for Shidduchim

For someone who considers herself intelligent, she made a comment that was not only unwise, but deeply offensive. Offensive enough that I knew instantly I could not, in good conscience, introduce her to any quality young man I know. What made it even more striking was that this conversation took place shortly before Purim, a…

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The Laws of Attraction in the Parsha

The Law of Attraction: Shidduch Lessons from Bnei Yisrael’s Travels in the Midbar It’s easy to associate shidduchim with this week’s parsha because of Kriyas Yam Suf. Chazal famously compare finding a spouse to the splitting of the sea. But there is another theme in this parsha that feels especially relevant to today’s dating world,…

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