The word “maybe” in English is neutral; it belies not the speaker’s preference regarding the possibility of which he speaks. The same is true of the Aramaic words dilma/shema* (“maybe”). Rabbi Shlomo of Urbino (a 16th century Italian scholar) writes in Ohel Moed (a lexicon of Hebrew synonyms) that the Hebrew word ulai likewise has a neutral charge. However, two other Italian grammarians who lived at the same time disagree. Rabbi Eliyahu HaBachur (1469-1549) in Sefer HaTishbi and Rabbi Immanuel Benevento in Livyat Chenwrite that in Biblical Hebrew there is no neutral word for “maybe.”
Instead, there are two different words for “maybe”, each of which carries implications as to the speaker’s preference for the possibility which he introduces with his “maybe”: Using the word ulai as “maybe” implies that the speaker desires that possible outcome, while using the word pen connotes the speaker’s hopeful rejection of that outcome. Malbim similarly writes that the word ulai implies a certain desire for the realization of this possibility or implies the recognition that this possibility is more likely to materialize than the alternative.
To illustrate this distinction, we can use an analogy: if one says, “I bought a lottery ticket because maybe I will win”, the Hebrew word ulai is appropriate. On the other hand, if one says, “I wear a seatbelt because maybe I will get in a car accident”, then the Hebrew word pen is appropriate.
This distinction is also somewhat supported by linguists. Some experts explain that the word ulai is a portmanteau of the words oh lo (“or not”) or is related to the Hebrew word loo or the Aramaic word levay (which mean “if only”). Rabbi Yaakov Tzvi Mecklenburg (1785-1865) argues that the word pen is related to the Hebrew verb panah (“turned away”) because it connotes the speaker’s hope that the listener will “turn away” from the unfavored possibility which he raises.
Rabbi Eliyahu Kramer of Vilna (1720-1797), better known as the Vilna Gaon, made famous the idea that the Hebrew words for “maybe” differ from their English and Aramaic counterparts by applying it to exegesis: The Torah relates that Eliezer was commissioned to seek out a suitable wife for Yitzchak in Abraham’s Mesopotamian homeland and to bring the maiden back to the Land of Canaan. When presented with this plan, Eliezer raised the possibility that the girl in question might not want to follow him to the Land of Canaan, “…maybe (ulai) the woman will not follow me…” (Gen. 24:39). Rashi explains that embedded in this clause is Eliezer’s secret desire to see his own daughter marry Yitzchak. Where did Rashi see this ulterior motive in Eliezer’s words? The Vilna Gaon explains that Rashi saw this in Eliezer’s word choice, which used the word ulai to introduce the possibility that the girl will not want to follow him, instead of the word pen. Had he used the word pen, Eliezer would have demonstrated that he truly wants his mission to the East to succeed, and remained hopeful that the girl would not refuse to follow him. However, because he used the word ulai, Eliezer showed his true colors that he had a hidden hope that the suitable girl would not want to travel to Canaan, so that his own daughter could marry Yitzchak.
Nonetheless, there is a significant problem with how HaBachur, Rabbi Benevento, and the Vilna Gaon explain the connotation of the word ulai. The Torah tells the story of how Yaakov received a special blessing from his father Yitzchak by impersonating his hairy brother Eisav. When Rikva first proposes to Yaakov that he pretend to be Eisav, Yaakov notes that his father could easily detect the ruse by simply feeling Yaakov’s smooth body and realizing that he is not Eisav. In Yaakov’s own words, “Maybe (ulai) my father will feel me…” (Gen. 27:12). If the word ulai implies that the speaker wants that particular possibility to come true, then why would Yaakov use the word ulai to introduce the possibility that his subterfuge will be discovered?
Maybe my father will feel me…
The commentators answer that Yaakov is most associated with the commitment to the truth. In fact, the prophet Micah (7:20) explicitly associates Yaakov with “truth” (and Avraham with “lovingkindness”). Accordingly, Yaakov actually wanted his father to feel him and put an end to his deception. He was so concerned with the truth that he felt uncomfortable passing a lie to his father, even if justified. This answer is proposed by a bevy of commentators, including, Rabbi Yehuda Leib Edel (1760-1828), Rabbi Tzvi Hirsch Chayes (1805-1855), Rabbi Seligman Baer (Yitzchok Dov) Bamberger of Würzburg (1807-1878), Rabbi Shlomo Aharon Wertheimer (1866-1935), and Rabbi Zalman Sorotzkin (1881-1966).
Rabbi Mecklenburg too argues that Yaakov wanted his father to feel him, but not in the context of realizing his ploy, rather in the context of placing his hands over Yaakov’s head when giving him the special blessings. Alternatively, we could answer that according to the Malbim (cited above), the term ulai does not necessarily imply that Yaakov wanted that to happen, but that he simply felt that it was most likely to happen. (Rabbi Wertheimer uses a similar argument to justify the appearance of ulai in Gen. 18:28.)
* NOTE: Although the Aramaic word for “maybe” (spelled SHIN-MEM-ALEPH) is traditionally pronounced shema (with a kamatz under the MEM), there are two alternatives: Rabbi Meir Mazuz (a contemporary Sephardic grammarian in Bnei Barak), basing himself on HaBachur’s vowelization of the word and on other sources, claims that the correct pronunciation is sheme (with a segol under the MEM). Alternatively, the oldest vowelized manuscript of the Mishna, known as the Kaufmann Manuscript, consistently vowelizes the word as shemay (with a tzayrei under the MEM).