Something happened 58 years ago that made it possible for me to be here writing these words.
My father attended a Shlomo Carlebach concert on Chanuka, and he noticed a young woman sitting by herself. He approached her and complimented her on her dress. She was visiting New York from Chicago and was there with a date, who had stepped away momentarily. She mentioned the name of the family she was staying by. My father called every family with that name in the phone book until he found the right one. He courted the young woman, who would later become his wife and my mother.
That could never happen today.
For starters, the concert would have had separate seating for men and women, possibly even separate entrances. This would reduce the already slim-to-zero chance of salacious behavior occurring at a Jewish concert, as well as the possibility of single men and women meeting and marrying without complicated machinations. Had the concert taken place today, my parents would not have met there. They would not have attended it altogether.
If the concert did have mixed seating, it would be avoided by many singles who wish to be considered “frum”. If they were seen there, it might harm their reputation and ruin their chances of being fixed up on shidduch dates.
If “frum” singles did attend, the men and women would independently sit far apart from each other. They might furtively check each other out, but no one would make a move. It just isn't done. Instead they would pray that a married person would somehow make an introduction, thereby kashering an interaction with someone they might marry. Unlikely, of course, but one must have bitachon. If a married person didn't get involved, and they never saw the other singles again, it just wasn't meant to be.
If a man approached a woman and introduced himself, she would not react favorably. She would be embarrassed, uncomfortable, and turned off by his breach of modesty. She might be secretly flattered, but the intruder would have no chance without a married person “facilitating”. It just isn't done.
If the man complimented her on her dress, she would consider it harassment. Even frum single women have learned from the women's liberationists that a man should never compliment a woman on her appearance, though he had better notice it and appreciate it. In the frum community, singles have taken it even further to be on the safe side, and they do not compliment one another on anything until they become engaged or during the break-up speech. Never in between. It might send the wrong message – for example, that you like a person and appreciate something about them. This is considered affectionate and intimate, and is therefore appropriate only for people who have already decided to marry or to soften the blow of rejection. Otherwise, it just isn't done.
If the man tracked down her hosts so he could try to court the woman, she would consider him a stalker. Most likely his reputation would be tarnished forever, and he might even be threatened. Despite what the Gemara says, a man must not really search for his wife. This most definitely is not done. Only others may search for him.
Even if, despite everything, the woman consented to see him again, they would have to find a shadchan to set them up retroactively and act as an intermediary. The shidduch is considered impure unless it is kashered in this way.
In any case, this could not possibly happen today because she was already seeing someone else, and she continued to see him after my father began courting her. In fact, my father sometimes drove her to her dates. Back then it was perfectly normal to date more than one person at a time, until you went steady with someone. They understood that everyone was a free agent until they signed a contract, and they proceeded on a best-efforts basis. Sure, some people got hurt, but they generally got over it, and almost everyone got married.
Nowadays people still get hurt – they always will, despite the best of intentions – but more people than ever aren't getting married. It doesn't matter so long as singles don't ever date more than one person at a time, which means that one date will definitely not lead to marriage, and is therefore frivolous. That is just not done.
I'm very glad my parents were dating before all this shtick became enshrined as the way it was always done and the way it must always be.
I have come across countless frum people who lament the way things are done today, and Orthodox media regularly feature anonymous letters calling for “something to be done”. That inevitably means that other people, whose identities will not be hidden, will be the ones to do something, after which it might become safe for others to follow. I have seen these letters for decades. Nothing has been done, except more of the same things that make shidduchim a frightening, dreadful specter even for those who are blessed with success.
When people ask me what can be done to improve the shidduch world, I tell them that many things can be done, but the real question is what are they willing to do. That generally ends the conversation in short order, and demonstrates that a deeper discussion on what can be done is mostly irrelevant. When I make suggestions, I am told in earnest that it isn't done, or it can't be done, or it won't be done. Such people had best stop complaining about the shidduch world; they made their choice, and now they are nothing more than whiners.
Singles and those who care about them have to realize that making critical life decisions based on “it just isn't done” is the safe, comfortable option in the short-term, but not a wise path. Think of the truly fulfilled, successful people you know. Did they get there by always looking over their shoulders at what other people were doing and fall into line? Or was the pivotal moment in their success story specifically when they took a risk and didn't do what everyone else was doing?
Veering from “the way things are done” does not mean behaving irresponsibly, becoming a daredevil, violating halacha, or compromising one's values. It means taking charge of your life, deciding what gives you – specifically YOU – a chance to realize your dreams, then doing it and not caring what other people think. Ultimately it's your life, and you are responsible for it more than any other person in the world. Holding yourself hostage to what yentas think, or what you imagine they might think, is a miserable way to live, whether or not you ultimately get married.
You have to decide if asking that girl or guy out, or reacting favorably to someone who makes themselves vulnerable in that way, is something you shouldn't do just because they might disappoint you, or simply because other people aren't doing that. Is it more important to engage in frumkeit virtue-signalling, or pursue what could be the opportunity of a lifetime right before you? Do you want the story of your life to be that you gave yourself the best chance of realizing your dreams, or that you never colored even slightly outside the socially approved lines?
My parents came from very frum families and dated in ways that just aren't done today. I'm glad they did.
Maybe you should, too.