The debate over including Shir HaShirim in the Tanach is well known. Our tradition tells us that Rabbi Akiva was one of the voices who argued in favor of including Shir HaShirim in the Tanach (Yadayim 3:5). Therefore, it is not surprising to learn that many seek to contrast Rabbi Akiva's personal biography with his attitude toward Shir HaShirim and superficially this makes sense. Rashi does describe the plight of the maiden in Shir HaShirim as that of a "living widow" who longs for her husband and her youthful love for him. Rabbi Akiva's wife lived a similar life for twenty-four years and as she waited for her husband to return from his Torah studies she too was described as a living widow (Ketubot 62b). Others point out that in Shir HaShirim the male works as a shepherd and and the maiden is described as a bat nadiv, the daughter of a wealthy family. As it turns out, Rabbi Akiva worked as a shepherd for the wealthy Kalba Savua and later married his daughter, Rachel. (Kalba Savua means "satiated dog" for whoever came into his home, even if they were as hungry as a dog, would leave fully satiated.)

It is true that the parallels between Rabbi Akiva's life and Shir HaShirim are startling. Shir HaShirim is about love and Rabbi Akiva's life was turned around by the love he had for the daughter of Kalba Savua, who agreed to become his wife if he would commit to Torah study. The imagery of Shir HaShirim includes a shepherd and the daughter of a wealthy family who becomes "a living widow." Thus, some suggest that it would not have been difficult for Rabbi Akiva to see himself and his wife in this imagery. When Rabbi Akiva declares that whoever sings Shir HaShirim in pubs and bars has no share in the world to come (Tosefta Sanhedrin 12:5), he was chastising those who would make light of the power of love, leaving it for that crude and light headed atmosphere where people drink and sing without thinking.

One of the rabbis of the modern era famous for his great love is Rav Kook, who wrote about ahavat hinam, love that knows no reason. This is why it is so meaningful to note that Rav Kook, this modern master of love, in his introduction to Shir HaShirim  (Olat Re'iyah II:3ff) takes issue with those who would limit Rabbi Akiva's adoration of Shir HaShirim to the personal biography of his life. Rav Kook writes that such people are unable to truly comprehend what Rabbi Akiva was talking about when he declared Shir HaShirim to be the sanctum sanctorum of Jewish scripture.

Rav Kook points out that Rabbi Akiva's love had the capacity to transcend the personal and the scope of his love was not bound by the limits of his own romantic interests. If one is inclined to draw parallels between the life of Rabbi Akiva and his defense of Shir HaShirim, then one is better served by looking beyond the relationship of a husband and a wife. Instead we should recall that upon seeing foxes trampling where the Beit HaMikdash once stood, Rabbi Akiva was able to laugh because his heart was filled with love for a vision of a blissful future where Rome was gone and Israel returned to glory and this love that filled his heart could transcend the present sorrow and desolation (Makkot 24b). Rav Kook urges us to recall the martyred Rabbi Akiva whose love of Torah transcended fear of death and whose love of God transcended the pain of torture so that as he declared God's unity he was able to let go of his worldly life as he declared God's unity (Berachot 61b). This is the Rabbi Akiva, overflowing with love that transcends his personal situation, who sees the holiness of Shir HaShirim. Thus, to draw parallels between the private love of Rabbi Akiva and Shir HaShirim is to never lift the veil of allegory that covers over the meaning of this holiest of songs. If we wish to lift that veil then we must go beyond that love which is rooted in our private concerns.