The Talmud says those who marry for money will have unworthy children. Money should not be any consideration in a shidduch. Anything could happen at any moment – the poor could earn their merit and become wealthy. The rich could lose what they have. Don’t the gedolim warm not to rejoice too much – who knows what your aveiras could cause to happen next week.
Speaking of which, are you mad?
This $400k dollar marriage startup, were you joking? Were you serious? You would spend a vast fortune like that? There is a man in my community who can’t work a job. He’s starving for food each week. You can see he is a reincarnation and that’s his punishment – might have been a slanderer or arrogant last lifetime. But now, he is completely and utterly dependent on people’s charity. And I heard he’s doing chemo now so where is he going to eat?
And you would spend hundreds of thousands. Please tell me you were only joking….
If not… They say the test of wealth is harder than the test of poverty.
As for the son of a Rosh Yeshiva, well… so what. You don’t know what favour a simple unassuming man has in the regard of Heaven. Appearances are nothing. I have seen Torah scholars with shirts tucked out, or putting a chumash under a siddur, or flicking a sefer closed instead of gently closing it. And I have seen women in mini pants asking when a meat dinner is because she had pizza for lunch.
The best to look for is not necessarily education but middos – does he offer hospitality, does he have anger inside him or is he quick to forgive? These are a man inside his heart. Knowledge and familial connection are external and superficial.
And what’s this RUBBISH about showing off a pic to the family?! Gossip? Talking about someone behind their back? The Chofetz Chaim has volumes to say about that. Are those women bored with their time? The conversation will be banal and devarim bateilim. Empty talk.
And of course you give the dating man a pic of the lady. They swap pics of each other. That’s normal.