When Ben Azzai heard Rabbi Akiva’s argument, he exclaimed in this exact language: It is a pity to you, Ban Azzai, that you did not serve Rabbi Akiva!

The Yad Malachei asks: It is evident from this Gemora that Ben Azzai did not study under Rabbi akiva. However, the Gemora Brochos  (62a) states that Rabbi Yehudah told Ben Azzai: For how long will you be brazen towards Rabbi Akiva, your master? It could be answered that Ben Azzai went to study under Rabbi Akiva, and that is what the Gemora in Brochos is referring to.

However, the Gemora Brochos mentions that Ben Azzai said to Rabbi Akiva: For how long will you be brazen towards your master, that you followed Rabbi Yehoshua into the lavatory? If Rabbi Akiva was his master, how could he speak in such a degrading manner towards him? Even a teacher to a student wouldn’t talk like that; certainly a student to his teacher!

Therefore, he writes that it must be that Ben Azzai was a talmid chaver (a peer) of Rabbi Akiva. They were both disciples of Rabbi Eliezer the Great.

The Gemora in Bava Basra (158a) refers to Ben Azzai as the “Talmid chaver” of Rabbi Akiva. Ben Azzai was considered somewhat of a disciple of Rabbi Akiva.

Rabbeinu Gershom comments: Since Ben Azzai was a “bochur,” he was unable to comprehend halachic logic as well as Rabbi Akiva.

What is the connection between being a “bochur,” and not comprehending to the fullest extent?

I once heard from my Rosh Yeshiva, HaRav Chaim Schmelczer zt”l that Rabbeinu Gershom means that Ben Azzai was a bachelor, and one who is not married does not have the same level of contentment as one who is married. Torah study requires one to be at ease; one must have a menuchas hanefesh in order to comprehend the depths of the Torah. This is what Ben Azzai was lacking.