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Good afternoon chevra, and welcome to Ketubot.
Here are a few essential ideas to guide us through this perek.
(1) Although the context of everything here is marriage, the discussion in our perek is fundamentally a monetary one. For reasons the Mishna does not discuss (though see below), every groom is required to make a financial commitment (called "ketubah") to his bride, that she can claim upon being divorced or widowed. The commitment is 200 maneh if the bride is a virgin, and 100 maneh if she is not. And as is true whenever a person carries a financial liability, there are going to be times when that person goes to court and argues that, for one reason or another, he should be freed of that liability. And the same can happen with a groom.
Our Mishnayot present the general criteria for determining whether a particular marriage comes with a ketubah commitment of 100 or of 200 maneh, as well some of the rules for adjudicating claims when they land in Bet Din.
(2) The claim that the groom is here making to release himself from his financial liability to his wife is that on the night of their wedding he discovered that she is not a virgin. As the Mishnayot make clear, this claim only has validity (very logically) if the assumption had been that she was a virgin, for which reason he had made a ketubah commitment of 200 maneh to her to begin with. His claim is meaningless in cases in which he had no right to assume to begin with that she was a virgin.
(3) Though it doesn't come up directly in this perek, it's important to note that the groom's claim also has other consequences. The mere claim on his part that the "virgin" whom had betrothed some months earlier was found to not be so on the night of of their chuppah raises the possibility that she had committed adultery during the betrothal period, rendering any further sexual contact between them forbidden. In other words, even though the court still has to do its work in terms of trying to verify the facts of the matter, his claim has already altered their relationship.
(4) Noteworthy is the dispute that runs through Mishnayot 6, 7, and 8 in which Rabban Gamliel and Rabbi Eliezer consistently rule that the bride is to be believed about her sexual past (in the absence of either party having witnesses to anything), and Rabbi Yehoshua takes the opposite position. (The halacha follows the former in all of these cases.)
Just circling back to the reason that the sages imposed the ketubah commitment upon grooms to begin with: The gemara explains that the sages did so to discourage men from casually, or in a moment of anger, divorcing their wives. It was hoped that the fact that the decision to divorce would carry serious financial implications would lead to more thoughtful behavior. The sages struggled to find the "goldilocks" amount of money that would be high enough to have the desired effect on the impetuous husband but not so high that it would discourage men from marrying to begin with. This is how they arrived at 200 maneh for a virgin bride and 100 for others.
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