Is it true that a wedding ring should be round on the inside and square on the outside

Hello and blessings

A. Some are accustomed to making the ring round on the inside and square on the outside, based on the implication of the language of Tikunei Zohar, Tikkun 5 (page 19a), that the ring is in the form of the closed letter mem. So wrote the holy gaon, author of Zohar Chai, from Kamarna, as well in his introduction to part 1, page 4a, that one should betroth with a ring that is in the form of the closed mem, and this is his wording: "Thus one should make a ring, according to the custom of my master and teacher [that is, the holy gaon, our teacher Rabbi Tzvi Hersh of Ziditchov, author of Atzeret Tzvi, of blessed memory] square on the outside and round on the inside, etc., and it is for a good sign and for good fortune, so that there should not be, Heaven forbid, two opposites, but rather they should give birth one from the other and this one from that one through a proper and holy union in holiness and purity."

He further wrote there in Zohar Chai (on page 20, column 4) as follows: "I received from my teacher, my holy uncle Tzvi, that the betrothal ring must be round on the inside and square on the outside, in a complete square, like two dalets, etc., and one who makes such a betrothal ring from the husband’s money specifically will be assured that his wife will not be barren all her days" etc.

See there. However, it is known and clear that the vast majority of the luminaries of the generations, and even great kabbalists and giants of Chassidut whose conduct was generally according to Kabbalah, did not instruct in this way to make the betrothal ring square like a closed mem, and they followed the simple custom in the communities of Israel to betroth with a regular ring, round both inside and outside. So too, this is established among the Sephardi kabbalists of Jerusalem, students of the holy gaon Rabbi Shalom Sharabi, of blessed memory, that the custom is to betroth with a round ring and not a square one. This is also implied elsewhere in Tikunei Zohar (Tikkun 10), that the ring is round in the form of the letter yud.

Moreover, the holy Shelah brought clear language from HaChayit [who was among the greatest of the early kabbalists], and this is his wording: "For the ring with which we betroth is round, in the form of the yud in the Name" etc. Some have argued that the form printed in the Zohar as the letter mem is an error, and it should be read as the form of the letter samech, which is round. 

B. I did not understand the question regarding entering the chuppah; whether the meaning is who serves as the shoshvinim to escort the groom and the bride beneath the chuppah. Or something else; please clarify again. 

C. The bride does not recite anything in a traditional Jewish chuppah. She may bless the groom after the chuppah with a blessing that both of them should succeed and live together in happiness and joy. 

Success - Menashe Yisrael