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This might sound strange but the effective Jewish Halacha allows for marrying multiple women at once:

נוֹשֵׂא אָדָם כַּמָּה נָשִׁים אֲפִלּוּ מֵאָה בֵּין בְּבַת אַחַת בֵּין בָּזוֹ אַחַר זוֹ - A person can marry several women simultaneously or once after another. Rambam Mishneh_Torah%2C_Marriage.14.3

To my best knowledge, Yaakov already knew his destiny of marrying the two sisters, he only wished to marry them in the opposite order. Lavan was also eager to marry off the two to Yaakov.

Marrying Rachel and Leah at once would save the hoax of switching between them and start the happy marriage from the right foot.

So why didn’t Yaakov marry both sisters simultaneously?

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  • Lavan would presumably never have allowed it. Either that, or he would have changed the terms of his service for much longer. Yaakov knew he was a deceptive person. See Rashi on their agreement - sefaria.org/… – Dov Nov 28 '20 at 21:22
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    Your entire question rests on the premise that Yaakov already knew he would marry Leah. Without a source for this claim, the question does not seem so compelling. – Alex Nov 28 '20 at 22:43
  • He can't mix the sheva brachos. Ein marvin simcha bisimcha...chazal just say kiddushin works, not that you should do it. – Shlomy Nov 29 '20 at 20:21
  • See Pri Megadim O"C 546:1 where he asks a (somewhat) similar question. Unfortunately, he does not answer it directly, and directs you to look at the "רא"ם פרשת ויצא", which I am not sure what that is. – Salmononius2 Nov 30 '20 at 2:32
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I remember reading Chazal to the effect that he was abiding by the halachic rule that you don't mix two sources of rejoicing ("En mearvin simchah be-simchah"). [Tosafot on Moed Katan 8] The patriarchs observed halacha according to tradition. And he could marry two sisters because the sisters were converts, and converts lose their family ties upon conversion, so they weren't halachic sisters.

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