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?
Answer
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.
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