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Bottom line – is the boy a mesnch, is the girl a baalas chessed, do they care enough about other people that they can learn to care about each other? Are they mature, or are they simply being told it’s the “right” time to get married? Do they understand that there is no money tree growing in their respective parents’ backyards, and at some point they will need to make their own way in the world, and when that day comes, can the boy earn the living, especially if the wife suddenly cannot (difficult pregnancy, issues with babysitting, etc.)? Are the girls realistic about what marriage entails, or are they living in a dream world spun by their various seminaries? Are they both hashkafically on the same page or enar each other? OK, redd the shidduch!