Yaakov Avinu spent all his life learning Torah, before he went to Aram to find a wife. He knew the Torah way of life. He wanted to marry the younger sister Rochel, and did not see any problem with it. The Torah way of life, according to Yaakov Avinu, is such that it makes no difference who gets married first.
The Way of Lavan
Then came the wicked idol-worshiper Lavan, and made trouble. Lavan is the one who decided that the older sister must get married first. Lavan is the one who placed Leah instead of Rochel. Now, that he did it, Rochel had no choice but to save Leah from embarrassment. Not the embarrassment of her younger sister getting married first, but, the embarrassment of being exposed as being placed there by her father Lavan. Rashi explains: "now will my sister be embarrassed", which means that earlier, when Rochel was going to be married first, the older sister Leah was NOT embarrassed.
What the Rabbis Say
Rabbi Aharon Fried, in his book Tzel HaKesef ch.18, says that we must follow the way of Yaakov Avinu because he knew that there is nothing wrong with marrying a younger sister first. He explains that Lavan invented this false argument only in order to justify his wickedness and to pretend to be righteous in the eyes of Yaakov. Therefore, we are PROHIBITED from believing and following Lavan's wicked invention. Many other Rabbis said the same. They advocated the way of Yaakov Avinu (which means that the order does not matter) and PROHIBITED following the wicked invention of Lavan.
The Jewish way of life, in accordance with the Torah, is called "Judaism". Lavan's tendency to hurt others while pretending to be righteous should then be called "Lavanism". Do we really want to import Lavanism into Judaism? Anyone who believes that an older sister must get married first is, in fact, declaring that Lavanism is senior to the Torah way of Yaakov Avinu. Anyone who believes that an older sister must get married first is also finding fault in Yaakov Avinu (who wanted to marry the younger sister) while justifying Lavan.
One question which can come to mind is: "Why did some Rabbis say that an older sister should get married first?" This is the wrong question. The real question is: "How is it possible to find fault in Yaakov Avinu and to justify Lavan?"
There are those who say that we have to follow Lavan's argument because it is mentioned in the Torah. In that case, there are many other sins and evils mentioned in the Torah. Do we have to follow all of them too? Lavan continuously defrauded Yaakov and did not pay him for his work. Defrauding workers out of their wages - wage theft - happens to also be a problem in America. The state of New York has developed a list of known frequent wage thieves. "Hassidic Jew" is, unfortunately, also on this list. The same "Hassidic Jews" who were labeled by the state of New York as frequent wage thieves are also the ones who believe that Lavan's faulty ideas on the order of marriage need to be imitated. Is Lavanism a genetic leftover from 3500 years ago?
Embarrassment and Fear
Who gets married first is not a win-lose game. If any embarrassment could have been caused by marrying a younger sister first, Yaakov Avinu would not have wanted to do it. Yaakov Avinu knew that marrying a younger sister first does NOT involve embarrassment. It is Lavan who invented this concept to justify his wicked behavior and to pretend to be righteous. Why should we imitate the faulty ideas of the wicked idol-worshiper Lavan? In some Jewish groups this is a prevalent social/religious misconception. In these groups, it has been accepted that Lavan's invention needs to be imitated. It is not a surprise, then, that Lavanism and wage-theft are both prevalent in these same groups. In other groups, which have not accepted Lavan's faulty ideas, this is not a problem at all.
Older sisters may have personal feelings in this regard, but, these feelings are not to be confused with any form of social embarrassment. One of girl's greatest fears is the fear of never getting married. Some girls believe that if a younger sister gets married first, then, she, the older sister, will never get married. What these older sisters do not know is that this fear is a by-product of Lavanism. Practically all the girls do get married, and the time when they get married has nothing to do with whether a younger sister does or does not get married first. Yes, there are older sisters who do not get married just like there are older brothers who do not get married. In most cases this is a result of "self-fulfilling prophecy". If I believe something, I make it happen to prove myself right. Another common cause is described by "You create what you fear the most". Fear is a very powerful tool with which we create situations to prove that our fear was justified.
The Kabbalistic Approach
A father took his two daughters to a Kabbalist in Eretz Yisroel, when his younger daughter got engaged before the older daughter. He wanted to ask for the Kabbalist's advice on what is the right thing to do. The Kabbalist told him to go ahead with the younger daughter, as it makes no difference who gets married first. "Isn't it the rule that the older sister needs to get married first?" asked the father. The Kabbalist admonished the father and said: "Who are you, Lavan?"
The Kabbalist knew what so many Rabbis ignore. The Kabbalist knew that there is no room for Lavanism in Judaism. We don't have a Mitzvah to imitate Lavan. Lavan was so wicked that it should be PROHIBITED to imitate him in any way. If we do imitate Lavan and turn it into a social/religious standard, all we do is promote Lavanism and cause pain and social embarrassment to the older sisters. It is not the younger sister getting married first that causes the embarrassment. It is this faulty social/religious standard of Lavanism that causes the embarrassment.
The idea as if there is embarrassment to the older sister, when a younger sister gets married first, is a total misunderstanding of what happened with Rochel and Leah. When Rochel was going to be married first, there was no embarrassment to Leah. The Idea that the older sister must get married first is the wicked Lavan's idea, and that's what causes so much embarrassment to today's older sisters. Lavan wanted to hurt Yaakov and his descendants while pretending to be righteous. Now, by imitating Lavan, by importing Lavanism into Judaism, we help him succeed.
Let Go of Your Banana
The social/religious standard as if an older sister must get married before her younger sister, is pure Lavanism. It is not the Torah way of life that we learn from Yaakov Avinu. Holding on to Lavanism is like a monkey getting trapped by holding on to a banana, not being able to pull his hand back out and escape.
If you want to be happy and free and successful, let go of your banana.
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