I read about a girl who was concerned that a bochur she was dating took his hat off once he got into the car he drove on the date.
This is nothing less than SCANDALOUS!!!!
The slippery slope is DANGEROUS!!!!!
Next he will take off his hat when showering, when going to the mikva and before he puts on his shel rosh so that the tfillin can fit on his head!!!!
A TRUE Bas Yisroel should IMMEDIATELY cut off contact with such a bochur.
My wife, nebuch, once dated a bochur who DIDN'T WEAR A HAT AT ALL [except for a NY Mets and Miami Dolphins cap]. Then she made the mistake of MARRYING this *shaygetz*. And look at him now..... An Am Ha-aretz Gamur with a doctorate in "Oisvarfology". A schlemiel to the thousandth power. And it all started b/c he didn't wear a hat.
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Ahhhhhhhhhhhhhhhhh - Tyere Yidden. I have know so many sweet holy Jews who rachmana litzlan go hatless. It is OK. Really not the end of the world. Chaim Walder wore a hat. Berland wears a hat. There are hat wearing child abusers and hat wearing wife beaters and hat wearing embezzelers and hat wearing נואפים. They wear real black hats and somehow still manage to be רשעים.In the daily minyan at Beis Knesses D'Otisville you will find hats. When a former Israeli Chief Rabbi sat in jail for his "mitzvos", he wore not just a hat but a chashuve "Homburg".
So young ladies remember: The ikker in life is one's heart and one's actions. Does he love Hashem and serve Hashem with all of his heart and does he have middos tovos. The hat matters b/c it shows that identifies with the community of people who are serious about serving Hashem and it separates him from the outside society but that is not the most important thing.
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There was once a popular book by Dr. Oliver Sacks "The Man Who Mistook His Wife For A Hat". As an old friend of mine once had it: Don't mistake your LIFE for a hat.