יִמְצָאֵהוּ בְּאֶרֶץ מִדְבָּר וּבְתֹהוּ יְלֵל יְשִׁמֹן יְסֹבְבֶנְהוּ יְבוֹנְנֵהוּ יִצְּרֶנְהוּ כְּאִישׁוֹן עֵינוֹ
He found him in a desert land, and in the waste, a howling wilderness; He compassed him about, He cared for him, He kept him as the apple of His eye.
Ishon is also a pupil – The Tiferes Shlomo says that this passuk is specifically referring to one of the special aspects of Sukkot as a time specifically to work on shmiras einayim – guarding of one’s eyes (pupils). We ask in Mussaf on the Shalosh Regalim: v’hareinu b’vinyano – to see the building of the Beit HaMikdash. Only with einayim tehorot can we behold sights of kedusha.
Rav Schorr writes that we go into the Sukkah as a haven, so to speak, from the outside world. Inside the Sukkah, we see the stars and the faces of our family and friends, G-d willing.
The third bracha of Bilaam is the famous blessing of Mah Tovu Ohalech Yaakov…Bnei Yisrael are praised for their modesty (because the entrances of their tents did not face one another).Shmiras einayim, however, is not only about shielding our eyes from improper sights and images; sifrei mussar also speak about this trait in connection with not looking upon others in a disdainful, critical, judgmental or jealous manner. Sukkot comes immediately after Yom Kippur – a day during which we hope to rectify our actions and turn bad habits around. A humble suggestion, that perhaps one function of the Sukkah is to emphasize not looking at other people after Yom Kippur and think either (1) that they didn’t use Yom Kippur properly, or (2) the opposite – seeing someone trying to correct their ways, and thinking “who does this person think he/she is; all of a sudden this person is frum…etc.”.
וְעַל חֵטְא שֶׁחָטָאנוּ לְפָנֶיךָ בְּשִׂקּוּר עָיִן
עַל חֵטְא שֶׁחָטָאנוּ לְפָנֶיךָ בְּעֵינַיִם רָמות
Why the double-eye language? Rav Schorr quotes the Taharat Kodesh, who says that the amount a person is careful with what he looks at in the world (and how he looks at his fellow man) before Mashiach, will be commensurate with how much he WILL be able to see upon the arrival of Mashiach, b’meheirah b’yameinu.