A man may betroth by himself and through an agent, and a woman may become betrothed by herself and through an agent. A man may have his daughter betrothed when she is a na'arah [a pubescent girl distinguished from a prepubescent girl and a post-pubescent young women in a number of halakhic situations], by himself and through an agent. [With regard to] one who says to a woman, "Be betrothed to me with this date, be betrothed to me with this [one];" if in one of them there is [at least] the value of a perutah, she is betrothed, and if not, she is not betrothed. [If he says,] "With this one, and with this one, and with this one," if there is [at least] the value of a perutah in all of them [combined], she is betrothed; and if not, she is not betrothed. If she was eating them one by one [as he gave them to her], she is not betrothed unless there is the value of [at least] a perutah in one of them.

[If one says to a woman,] "Be betrothed to me with this cup of wine," and it is found to be of honey; "Of honey," and it is found to be of wine; "With this dinar [a specific unit of money] of silver," and it is found to be of gold; "Of gold," and it is found to be of silver; "On condition that I am rich," and he is found to be poor; "Poor," and he is found to be rich." [In all these cases] she is not betrothed. Rabbi Shimon says, "If he deceived her to [her] advantage, [she] is betrothed."

[If one says to a woman, "Be betrothed to me] on condition that I am a kohen," and he is found to be a Levite; "A Levite," and he is found to be a kohen; "A netin [a Gibeonite]," and he is found to be a mamzer [the offspring of certain prohibited relationships who may not marry into the general Jewish population]; "A mamzer," and he is found to be a netin; "A village-dweller," and he is found to be a city-dweller; "A city-dweller," and he is found to be a village-dweller; "On condition that my house is near the bathhouse," and it is found to be far; "Far [from the bathhouse]," and it is found to be near; "On condition that I have an older daughter or maidservant," and he does not have; "On condition that I do not have [an older daughter or maidservant]," and he does have; "On condition that I do not have sons," and he has; "On condition that I do have [sons]," and he does not have. And in all [of these cases], even though she says, "It was in my heart to be betrothed to him even so," she is not betrothed. And the same is true [in cases where] she deceives him.

One who says to his agent, "Go out and betroth on my behalf a certain woman in a certain place," and he went and betrothed her in another place, she is not betrothed. [However, if he said,] "Behold, she is in a certain place," and he went and betrothed her in another place, she is betrothed.

[With regard to] one who betroths a woman on condition that she is not subject to any vows, and there were found to be vows to which she is subject, she is not betrothed. If he married her without conditions, and there were found to be vows to which she was subject, she leaves without a ketubah [monetary settlement payable to a woman upon divorce or the death of her husband]. [If one betroths a woman] on condition that she has no blemishes, and blemishes were found on her, she is not betrothed. If he married her without conditions, and blemishes were found on her, she leaves without a ketubah. All blemishes that disqualify kohanim disqualify women [in marriage].

[With regard to] one who betroths two women with the value of a perutah, or a single woman with less than the value of a perutah, even though he sent betrothal gifts after this, she is not betrothed, as it was on account of the original betrothal that he sent [them]. And the same [is true for] a minor who betrothed [a woman].

[With regard to] one who betroths a woman and her daughter or a woman and her sister simultaneously, they are not betrothed. [There was] an incident with five women, and among them [were] two sisters, and one [man] gathered a basket of dates. [The basket of dates] belonged to them, but it was [fruits] of the sabbatical year. He said to them, "All of you are betrothed to me with this basket," and one of them accepted it on behalf of them all. And the Sages said, "The sisters are not betrothed."

[With regard to a kohen] who betroths with his portion, whether of sacrifices of the highest degree of sanctity or of sacrifices of a lesser degree of sanctity, she is not betrothed. [If he betroths her] with the second tithe, whether intentionally or unwittingly, he has not betrothed. These are the words of Rabbi Meir. Rabbi Yehudah says, "[If] unintentionally, he has not betrothed; intentionally, he has betrothed. And [with regard to betrothing a woman] with a consecrated item, [if he does so] intentionally, he has betrothed; unintentionally, he has not betrothed. These are the words of Rabbi Meir. Rabbi Yehudah says, [If] unintentionally, he has betrothed; intentionally, he has not betrothed.

[With regard to] one who betroths with orlah [the fruit of a tree during the first three years after its planting, the consumption or usage of which is forbidden], with kilei hakerem [the product of the prohibited planting of other species in a vineyard], or with an ox which is to be stoned [because it killed a person], or with a calf whose neck is to be broken [as part of a ceremony performed by the elders of a city when a corpse is found between two cities], or with the birds [offered as a sacrifice by] a metzorah, with the hair of a nazirite, or with the first born of a donkey, or with meat [mixed] with milk, or with non-sacrificial [animals] which were slaughtered in the [Temple] Courtyard, she is not betrothed. If he sold them and betrothed [her] with the proceeds, she is betrothed.

[With regard to] one who betroths with terumah [a portion of a crop given to a kohen which becomes holy upon separation, and can only be consumed by kohanim or their household], or with tithes, or with [sacrificial] gift portions [given to the kohen], or with the purifying water [used as part of the purification process of one who is impure due to contact with a corpse], or with the ash of the Red Heifer, she is betrothed, even if he is an Israelite [i.e., non-kohen].