In his meeting with Lavan and Besuel, Eliezer recounts that he asked Avraham before leaving: “Maybe the girl won’t come with me?” Rashi notes that the word, “ulai,” “maybe,” is written without the letter “vav,” so that if you didn’t know better you might read it as “eilai.” The Midrash explains that Eliezer had a daughter that he thought might be a prospective match for Yitzchak. Raising the question was Eliezer’s way of giving voice to his hidden hope that Yitzchak might marry “eilai,” into his own family.
The meforshei Rashi ask why this allusion appears only here, when Eliezer recounts the story, and not earlier, when he is speaking to Avraham directly. The Kotzker famously explains that it’s only after the fact, after he found Rivka, that Eliezer realized his own hidden motives. So long as he had a vested interest in the matter, he didn’t even realize how it tilted his perspective.
Another clever answer: before he came to Lavan and Besuel’s home, Eliezer thought his hava amina that Yitzchak should marry his daughter was ridiculous. But when he saw the mechutanim, Besuel, and he saw Lavan, he thought why not me?
The Ksav v’haKabbalah suggests that this Midrash is not based on the missing letter “vav” alone, but is based on the phrase used to pose the question. There are two different words that can be used to talk about “maybe”: the word “ulai” and the word “pen.” The word “pen” is used when you don’t want the possibility being discussed to happen -- the equivalent of the English “lest.” After Adam eats from the eitz hada’as, the Torah says, “pen yishlach yado v’achal gam m’eitz hachaim,” i.e. “lest he eat from the eitz hachaim.” The word “ulai,” on the other hand, is when you want the possibility being discussed to happen. Ya’akov sends gifts to Eisav because “ulai yisah panai,” i.e. “maybe he will greet me in peace.” Ya’akov wants Eisav to accept his gift, not to turn away. When Eliezer raised the possibility of Rivka not wanting to come with him, he doesn’t use the word, “pen,” i.e. “lest she refuse to come,” but rather he uses “ulai” – it was something that secretly, he wanted to happen.
This pshat gives you a new perspective on a key pasuk in our parsha. Rivka tells Ya’akov to dress up as Eisav and go to get brachos from his father. Ya’akov responds, “Ulai y’musheini avi,” i.e. “Perhaps my father will touch me [and feel my smooth skin].” Ya’akov doesn’t use the word “pen,” i.e. “I can't do it lest my father feel that it is not me,” but rather he uses the word “ulai,” indicating it is something he wanted. Despite his hesitancy to go into Yitzchak and deceive him, Ya’akov reveals in his question that he really desired for Yitzchak to place his hands on him, as that was the mechanism for the delivery of brachos.