Why did Yaakov offer to work seven years for Rachel?
Rashi: Those seven years were 'the few days' that Rivkah referred to 1 when she suggested that he go to live with her brother Lavan (Bereishis 27:64). 2
Seforno: The seven -year wait was to give him time to build up a Parnasah 3 - since the Gemara in Yevamos (65b) prohibits a man from marrying a woman if he cannot provide for her needs. Whereas the work was a 'dowry' which the prospective Chasan would give the girl's father for the privilege of marrying his daughter, as was customary in those days. 4
Moshav Zekenim: Even though the custom is for the girl's father to give a dowry, Yaakov said, "If you will not give for free, I will work for her, and not transgress my father's command to take a wife."
Tosfos ha'Shalem (1, citing R. Efrayim): An Eved Ivri serves for six years Yaakov wanted to work more than this. (Ohr ha'Chayim - he gauged that Rachel is worth more than this.) However, when he worked for money, Hashem did not want to him to work more than an Eved Ivri, and told him to leave after six years.
Tosfos ha'Shalem (7): Rivkah meant "Yamim," i.e. years, that are Achadim (units, and do not reach 10), i.e. nine. 5 Yaakov erred. He thought that they are units of Shemitah, i.e. seven years. 6
Refer to 29:15:1:3 and the note there.
Ohr ha'Chayim: Yaakov always humbled himself seven-fold - he also bowed seven times to Esav (33:3). This is based on "Sheva Yipol Tzadik v'Kam" (Mishlei 24:16).
Ner Uziel (p. 174): Yaakov estimated that he needs seven years to perfect himself more before he is ready to marry Rachel and fulfill his mission. (Refer to 29:20:1:6, and the note there.)
Gur Aryeh: How do we know this is what Yaakov meant? Otherwise, why should he have offered seven years, when his mother had advised, 'a few days'?!
Rivkah said, "a few days, until your brother's anger subsides, and I will send and take you from there," and she later sent Devorah to get him (see Rashi to Bereishis 35:8). This implies that he did not know how long it will be! Perhaps Yaakov understood that it will be at least seven more years, i.e. 21 from when he left. (PF)
Where do we find that Yaakov acquired wealth in the seven years? Was not all his labor 'payment' for Rachel? Rashi (30:30) says that [also] during the second seven years, only his sons' labor was "l'Beisi" (but Lavan received all Yaakov's earnings)! (PF)
Tosfos ha'Shalem (3): And in seven years she will be an adult, and you will give to her a dowry, like the custom. See Shemos 22:16. Seforno - In the meantime, you can marry off Leah.
So Ibn Ezra (to Bereishis 27:44) explains.
Either way, the time finished in Yaakov's 14 years in the Yeshivah of Ever! It seems that his time in Yeshivah is not reckoned with, just like he was not punished for that time. Or, he thought that Rivkah limited how long he can stay with Lavan, lest he be influenced by him. (PF)
How did Yaakov agree to get married without a penny to his name, and how could he manage to provide for his growing family during the fourteen years that he was about to work for Lavan?
Seforno: Since the Gemara in Yevamos (65b) prohibits a man from marrying a woman if he cannot provide for her needs, Yaakov must have arrived with a considerable sum of money, 1 since his work was specifically in the form of a dowry 2 for his two wives.'
Oznayim la'Torah (to 31:39): Because, despite the fact Yaakov was working for Rachel, it seems that Lavan paid him a wage as well 3 - to the point that he was even able to pay him for the Tereifos that occurred in the flock. 4
Seforno: In any event, Lavan, who was a wealthy man, would never have given his daughter to someone who was not able to provide for her.
That the prospective Chasan would give the girl's father for the privilege of marrying his daughter, as was customary in those days.
Oznayim la'Torah: Which we are anyway forced to say, because otherwise how did he plan to return home after the fourteen years that he worked for Rachel - with a large family and no money with which to support them?
See 31:19.
Why did Yaakov see fit to add "your younger daughter"? How many daughters called Rachel did Lavan have?
Rashi: Anticipating Lavan's attempt to cheat him, he made it abundantly clear that he was working for Rachel his daughter, and not for some stranger from the street of that name, and for his younger daughter, and not for his older daughter whose name he would change to Rachel. 1
Seforno: Rachel was now a minor. By that time, Rachel would be ready to get married, and Lavan will have been able to marry off Leah.
Why wasn't Yaakov concerned lest Lavan change Zilpah's name to Rachel? She was younger than Rachel (Rashi to Bereishis 30:10)! She was a Shifchah, and not a proper daughter. Yaakov was not concerned for a double ruse (Tosfos ha'Shalem 4). Perhaps Lavan will father another daughter, call her Rachel, and she will be his youngest daughter! If it is clear that Yaakov refers to a girl in the world at the time, it is clear that he refers to the girl Rachel at the time! If Lavan switches the names, people might forget [when he did so, and] what that names were seven years ago. If new daughters are born, they can remember or see that they are less than seven years old! (PF)
Why did Yaakov love Rachel?
Ohr ha'Chayim #1: It was not due to her beauty, rather, because she was his Zivug. 1
Ohr ha'Chayim #2: He loved her because it is proper for a Chacham to have a pretty wife (Shabbos 25b), against the Yetzer ha'Ra (lest he be distracted due to thoughts of other women). Even though Yaakov was different, for he was void of the Yetzer ha'Ra, the Torah teaches Da'as. 2
Mishnas R. Aharon Vol. 3, p. 177: Yaakov's primary Midah was Torah, the active power of speech. Rachel's primary Midah was silence, the passive power of speech.
He inferred this from his Ru'ach ha'Kodesh that she will not be buried with him (Rashi to 29:11); or from his mother's words (refer to 29:2:152:1. - PF)
I.e. he should conduct like a Chacham, for others will learn from him. Surely he was void of the Yetzer ha'Ra, for he never had an emission before he married (refer to 49:3:2:1)! Our text of Shabbos 25b says "Ishah Mekushetes" (adorned). It seems that Ohr ha'Chayim had the Rambam's text (Shemoneh Perakim, 5 DH v'Cha'asher) 'Ishah Na'ah.' Brachos 57b says that a pretty wife is Marchiv Da'as; the Rambam implies that this helps to attain Chochmah. (PF)
QUESTIONS ON RASHI
Rashi writes: "... You may show that this is so, for 'they seemed to him like a few days' (29:20)." But that verse tells us that this was 'due to his great love for her;' not that they were objectively like a few days?
Gur Aryeh: Seven years is indeed what Rivkah had in mind. Nevertheless, Yaakov's difficult work as a shepherd should have seemed as a long time. Yet, because of his great love for Rachel, it seemed but a few days, despite the difficulty.
Rashi writes: "Why all of these stipulations? Yaakov knew that Lavan was a swindler...." Could he not have sufficed by saying, 'your youngest daughter'?
Gur Aryeh: Lavan could have claimed that the stipulation was, 'I would work even for your younger daughter' (and certainly for your older one); and given him Leah. Therefore, Yaakov specified Rachel by name.