In the modern orthodox world, a MAN or WOMAN is presented or viewed as an adult, with unique experiences, abilities and personalities. While all would acknowledge that losing a parent at a young age shapes a person–ultimately people are looking a the person who has been shaped. By analogy, often a person’s grandparents will have an influence on their life–but in the MO world no one really cares what shtetl in Lita or Ohio your grandparents came from; it is who YOU are now and what you, coupled with your personality and grace (or lack thereof).
In the charedi world BOYS and GIRLS are essentially variable fungible marriage units for marriage transactions. Yeshiva X, Bais Yakov Y; Flatbush Est 2?rd street; oldest youngest, Litvish, Galitzianer etc. Tall or short, oh and of some minor importance, rich or not rich. As people are setting up CHILDREN (in their mind) who have never accomplished anything of their own, all that matters is relative conformity to some ideal. Variation from the ideal is then weighed positively or negatively (balancing weight with wealth; measuring yichus against a sibling’s satorial choices). Families play a game where wining is defined by marrying better than you would have expected (by their crooked and warped sense) and losing is marrying down.
[I note incidentally that since in the charedi paradigm "children" can not acheive anything on their own of worth, any educational or communal success (becoming a JD/MD/organizing a tomchei shabbat) or entreprenurial success (demonstrating ability to open a business) demonstrated by a child is actually viewed as a negative as it is a mark of non-conformity. similarly merely being older that the norm is cause for a non-conforming demerit].
So my sister a was head of GO at BY X and best camper at charedi “no pockets allowed on skirts” de jour. She also happens to be beautiful. Nonetheless because she had a widowed mother she was viewed as substandard merchandise. Fortunately, she was able to marry a prospective 2nd generation kollel candidate given my Mother’s willingness to provide an appropriate remedial dowery. As for my late father’s reputation as a baal chesed and baal tzedakah, suffice it to say that those midos/ot were unfortunately canceled out by his gonig to work My other sisters were able to obtain appropriate husbands who had corresponding handicaps, perhaps a lame sibling or attendance at a second rate HS. As they are all happy I suppose the system worked.
In the MO world, people actually cared about MY adult educational acheivements and career and about my own spiritual acheivments in both Israeli yeshivot and YU.
In summary, if all that matters is a resume that needs a healthy dose of conformity — a death in the family will be a black mark. If what matters is the person themselves then a fat schlub will fail on his own merit.
That was where I first got puzzled. "You mean the shadchan was still involved on the seventh date?" I asked. And then I got the answer that reminded me of why I don't actively redt shidduchim anymore. The mom's voice was incredulous. "Of course the shadchan is still involved! You think that kids this young should just be left alone to have to make important decisions like this?! They need someone with experience guiding them. Es past nit that they should be the ones to ask the delicate questions or to put themselves into situations that could get awkward if they don't know what the right answer should be."