As a mom of a son in the parsha, I have observed that it can be challenging and time-consuming for a boy to travel back and forth for dates (though in all honesty, the furthest out he has gone is a long drive to New Jersey), and the gas, tolls, etc. BEFORE the date even takes place, are often a consideration. Also, if a girl lives really OOT (i.e., the Midwest or LA), making a wedding so far away may be a problem for the boy’s side(key family emmbers might be able to afford to make the trip, or be of good health to do so). That being said, if the girl from OOT is his true basherteh, he should not let her OOT home be a stumbling block to his potential happiness.
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