There are a few Rashis today where two views of a verse are offered, the literal view and the midrashic view. One of them has always resonated with me, so I will speak about it briefly. The Rashi is here, at verse 11. Why did Yaakov cry when he met Rachel? Rashi offers two approaches:
1) He saw through Ruach Hakodesh that he wouldn't be buried with her.
2) More literally, He was sad he did not have the wealth and bling funds to whisk her away the way Eliezer whisked Rivka away with the jewelry.
I see the two explanations as connected. This is generally my approach, learned from my rebbeim, to see a conceptual connection between the literal read of a passage and its midrashic read.
What Yaakov saw when he met with Rachel is that his relationship with her would be rocky, would lack the ease of courting and living that his father had had. Eliezer found a girl, judged her worthy, brought her to her intended. She was perfect, Yitzchak loved her. the end.
Yaakov, due to the circumstances of his escape, had none of the ease Eliezer did. He knew that given his mess of a life at that point, his relationship status with Rachel would be in the "It's Complicated" category. The Shakespearean phrase "Star-Crossed Lovers" comes to mind. He understood, or intuited, how difficult it would be to gain Rachel's hand in marriage given his poverty and Lavan's already-known character and love of wealth. He felt that despite the love he felt for her immediately, it wouldn't be an easy marriage.
Thus Rashi's two peirushim are connected at the hip: His immediate source of sadness was his grasp that they would not be married with the ease his parents were married. His deeper source of sadness was the understanding that the difficulties would never really go away, up until the last and lasting union, i.e. of burial.
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