First,the parents of many baby boomers were Holocaust survivors.
They had and tried to instill in us Emuna Peshuta, this is what Hashem wants/expects us to do and if we did have questions they tried to help us understand. If not, the schools in those years had teachers were examples of Torah and that helped too. And so too when it came to shidduchim, it was usually a friend, acquaintance who read a shidduch. Even if the backgrounds were different, there was trust that if Mr. or Mrs. so and so redt this for us, there must be something to it. So in one family you can find children marrying to diff backgrounds, such as diff sects of Chassidus, Litvish and sometimes even a frum YU type.In regard to choosing a son in law, my mother would say, we take the boy,not a boy!
Remembertoo there was one telephone with a short cord so there was not so much unecessary talk and gossip. One had a chance to think b4 they spoke. Today, too many people run to discuss such as issues with just anyone and everyone including shidduchim being redt.They speak b4 they think! Yes, there are many who wait for the phone to ring but there are others who just say a flat NO to shidduchim on no basis at all and 5 yrs. later they forget and wonder why barely a shidduch is redt to them.
Here is an example of a baby boomer marriage of about 45-50 yrs ago.An acquaintance of mine tells the story of her sister in law from a Chassidish/Heimish(no shtreimel) background who married a
Litvish boy from Lower East Side. One night, about 2-3 months after the wedding, the young woman shows up at her parents house saying her husband is different,meaning his customs and this is not for her. Her parents nicely told her, “you married him, this is your husband and you follow his customs”. What are the chances of something like this happening today.
Some of the at risk kids want to be a little diff but the family won’t accept it so they just go extreme.
Another point, which is not on subject. Many of the at risk are behaving just like the person who raised them, the babysitters who were not from unzere. Till they were little their mother dressed them in her taste and felt she was in control when at home. Once these kids are grown they do their own! At a wedding in Canada the kallah gave her Spanish maid the first dance and told her mother “she raised me so she is first”,true story. The mother’s tears were too late and wasted at this point.
Yes, we should have events such as Tu Baav that would cater to those who really want to get married not have a good time and talk narishkeiten.