It is written somewhere (I don't remember exactly where) that 40 days before conception, it is called out in Heaven who that person will marry. However, if the person gets married multiple times how does that work. Are the other marriages also called out? And what if the person doesn't get married?
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Try this lecture from Rabbi Bednarsh, entitled "the theology of shiduchim." Not surprisingly, there are many different opinions.
The Gemara sounds like a first marriage is easy, because it's just the two people matching up as pre-destined. It's second (or later) matchmakings that are "as difficult as the Splitting of the Sea."
The approach that's easiest for me to understand is that which R' Aryeh Kaplan zt'l quotes in his book on marriage (I don't recall which Rishonim he's citing): at conception, it is most likely that Chaim Yankel will go about his life in such-and-such a fashion, and Zlota Shprintza will be the right person for him as their first marriage. (Now it's possible that G-d provided Chaim with Zlota's "shiduch resume" but he was too picky to consider it, or they saw each other someplace he was too nervous [or frum?] to walk across the room and say hello to her, and thus he's still single; that's Chaim's fault, not G-d's!) Both Chaim and Zlota, however, are able to exercise free will and dramatically change their trajectory of life, at which point their Divinely-set "bashert" is ... I guess the word is "recalculated."
In short, just because a couple should get married doesn't mean they will.
There's also some discussion about why you're allowed to get engaged during the Nine Days, "as if you don't get this great girl, maybe someone else will"; that would seem to imply that even if was bashert, there are no guarantees; but I've heard other explanations too.
A lot of this has already been covered in other answers here.
There are three statements the Gemara brings:
The Talmud (Sotah 2a) reconciles the first two statements by saying that the first marriage is predetermined, and the second (and implicitly any subsequent match) is based on the persons deed (i.e. whether he is a wicked or righteous man he will get a wife he deserves).
The different interpretations of the story mentioned in number 3 have practical ramifications. Different commentaries have different opinions how successful a marriage will be if someone "stole" someone else's predestined bride through prayer, and interpret the story differently based on that.
There are Kabalistic, non-literal interpretations of what "First Marriage" and "Second Marriage" mean. by explaining the "first marriage" non-literally, they say that even the first time one gets married his spouse is determined according to his actions.
The Lubavitcher Rebbe was once asked how much of a person's choice in his spouse is free will, and how much is predetermined. In his response, the Rebbe lists 7 different opinions in Torah, ranging from fatalistic to Kabalistic, and then explains what Chabad Chassidic thought is on the matter.
Here is a bullet point summary of the different opinions, read the above links for more details and sources.
Perhaps the Medrash is simply suggesting that a person has a certain "type" that they are attracted to. In other words, we each have different personalities, psychological and biological causes which make up whom would be our ideal mate. The Chazal is saying that there is a certain type of woman whom we are attracted to. This already in our "nature". It doesn't mean there is a particular girl for you. It just means a "type".
This would solve all the questions regarding divorce, or people who married more than one wife (like Avraham), etc.
At our siyum on Sotah, a speaker noted an answer offered by R' Yitzhak Aramah, the author of the "Akeidas Yitzchak". It can be found in the eighth "Shaar", on page פ"ב in the edition of the book found on HebrewBooks.org: http://hebrewbooks.org/14342 . He rejects that any match, even for a first marriage, could be preordained, since it would render meaningless the good deeds and prayers of the righteous as they strove to find suitable mates. (E.g. finding a wife for our forefather Yitzchak.)
רק כונתם במה שאמר כאן בזווג ראשון באן בזווג שני היא אל ב׳ מיני הזווגים אשר היינו עליהם כי הקודם מהם אצל הטבע והיא חבור החמר אל צורה הנמצא בכל איש ואיש שעליו נאמר זכר ונקב׳ בראם ויקרא אח שמם אדם הוא אשר קראוהו זווג ראשון.
which means, roughly, "rather, when they said 'one is for the first match, one is for the second match' their intention is to refer to two different kinds of matches which pertain to a person. The first of them is the connection of the Substance and the Form inherent in every person, as it is said, 'Male and female created he them; and blessed them, and called their name Adam [Genesis 5:2]' -- that's what we call the 'first match'."
His interpretation of the above was, which body does which soul get. That is preordained.
There is a contradiction between two sources. The Shulchan Aruch writes that one can get married on Chol Hamoed because another can beat him to her. Another says that the bas kol decides 40 days in advance.
One of the answers given is that one can get married before to someone not his bashert, but will later on marry his bashert. Another is that he is more "predisposed" to her, but he can still marry someone else.
See Sotah 2a (summarized here). The pre-conception designation applied only to a first marriage. In subsequent marriages, one gets what one deserves, which is harder for God to arrange than the Splitting of the Sea.