It is in the form of a fabliau and tells the story of a miserly merchant, his avaricious wife and her lover, a wily monk. Although similar stories can be found in Giovanni Boccaccio's Decameron, a frequent source for Chaucer's tales, the story is a retelling of a common folk tale; "the lover's gift regained".
The tale tells of a merchant whose wife enjoys revelry and socialising, on which she spends much. A young monk, who is very close friends with the merchant, comes to stay with them. After confessing that she does not love her husband, the wife asks the monk for one hundred franks to pay her debts. The monk without her knowledge borrows the money from the merchant to give to the wife and she agrees with the monk:
When the merchant asks for his money back from the monk, the monk says that he has returned the loan back to the wife; and then promptly leaves town. When the merchant asks his wife about the money she says it is spent and blames the monk saying that she thought the money was in payment for him being such a long house guest. Instead of giving her husband the money back she says she will repay the debt in bed.
Apart from a criticism of the clergy, a common theme of Chaucer's, the tale also skillfully connects money, business and sex. Also the similar tales often end with both the wife and husband being conned but the addition of the wife, in turn, conning her husband seems to be Chaucer's own embellishment. As the wife is tallying her debt in bed the story ends on a bawdy pun that we should all, God willing, continue to "tally" the rest of our lives.
The use of the pronouns "us" and "we" when talking from a woman's perspective, along with the sympathetic portrayal of the wife in the tale, have led scholars to suggest that the tale was originally written for the Wife of Bath but as that character developed she was given a more fitting story and the Shipman took on this tale. In the line "he moot us clothe, and he moot us array," and others, "us" and "we" are used, in a way that a married woman might speak at that time. The Shipman may simply be imitating a female voice but the epilogue of the Man of Law's Tale in some manuscripts suggest it should be followed by the Shipman's tale rather than the Wife of Bath whose tale usually follows. The changes give some insight into Chaucer's development of the tales and the connections between them.
In the BBC1 adaptation of the Shipman's Tale (renamed the Sea Captain's tale), the setting is an Indian family in modern England. The monk's role is played by the merchant's real brother who has come from India to set up a shop in England. The wife, beset by money problems, sleeps with the brother who learns of her previous affairs through the merchant. The brother breaks up with her and the wife, feeling jilted, smashes his shop. The merchant subsequently sends his brother back to India with a warning, and at the end, he reaches across the bed to touch his wife's hand, a hint of possible reconciliation.