In Shakespeare’s time, marriages were usually arranged. A love match was unusual, and even more unusual was a woman choosing her prospective groom. Bertram’s objection to marrying Helena is rooted in these traditions. Because he is a count, he would have expected to marry someone of a similar status, not a commoner with neither wealth nor property to her name. A man would base his opinion of his prospective wife on the extent of her dowry, or marriage portion, which would include any land, money, or other goods, such as jewelry, which would become the husband’s property upon marriage (as would his wife). Helena had none of these, so Bertram considered her an inappropriate wife, regardless of her talents and personality.
As for the marriage ceremony, the king in All’s Well That Ends Well dispenses with tradition, which would have necessitated the Crying of the Banns, a public declaration of the couple’s intent to marry on three successive Sundays in their respective churches. This procedure allowed people time to voice objections to the marriage, for whatever reason. Exceptions to the Crying of the Banns were rare; ironically, Shakespeare himself was one of these exceptions, due to the fact that his prospective wife, Ann Hathaway, was already pregnant. As in All’s Well That Ends Well, certainly the king had the power to conduct a wedding ceremony without a prior Crying of the Banns.
Other traditions alluded to in the play include the expectation that the bride be a virgin. The bed-trick did indeed save Diana from ruining her life. Additionally, an exchange of rings was not uncommon, but it was not the norm. When Bertram states that Helena would never wear his ring, this would have been widely understood to mean that his ring on her finger would symbolize his acceptance of their union. Likewise, when Helena tricks Bertram into wearing her ring (the one the king gave her), she has succeeded in claiming him as would a bride who presented her groom with a wedding ring.
(extracted from) Shakespeare for Students:Critical Interpretations of Shakespeare’s Plays & Poetry, Second Edition, Volume 1, authored by Anne Marie Hacht & Cynthia Burnstein, published by Thomson-Gale, 2007