Marriage
In A Chaste Maid in Cheapside, it seems like everybody is either married or wants to get married. In fact, one marriage in particular, the intended marriage of Sir Walter to Moll Yellowhammer, creates the conflict in the play. Sir Walter has agreed to marry Moll and in return he has agreed to have Tim Yellowhammer marry his niece. This first arrangement also introduces the first deception. While Moll is in fact a chaste maid, as the title indicates, Sir Walter's niece—who is not his niece at all but a prostitute—is anything but the Welsh gentlewoman she pretends to be. As Sir Walter is riding into Cheapside with the Welsh gentlewoman, he instructs her in her deception. Sir Walter says, "Here you must pass for a pure virgin.'' Sir Walter also deceives the Allwits by not telling them that he is planning on getting married. He knows that if the Allwits suspect Sir Walter is getting married, they will try to stop it because, as a single man, he will continue to be their benefactor. When Davy tells Allwit that Sir Walter is intending to marry Moll, Allwit leaves hurriedly saying, "I have no time to stay, nor scarce to speak, / I'll stop those wheels, or all the work will break.’’ By this, Allwit refers to all of the hard work that he and his wife have put into making money off of Sir Walter.

While Sir Walter intends to marry Moll, she is really in love with Touchwood Junior, whom she wants to marry. Their attempts to marry are thwarted on several occasions. The first time, Touchwood Junior dupes Moll's father, a goldsmith, by having him make the ring that he intends to place on Moll's finger. Touchwood Junior is very bold in this ruse, telling Yellowhammer that he intends to use the ring to steal away a man's daughter. However, Yellow-hammer does not suspect that he is that man and so criticizes any father who is so blind. Yellowhammer says, ‘‘And parents blinded so, but they're served right / That have two eyes, and wear so dull a sight.'' However, Yellowhammer breaks up the marriage of Moll and Touchwood Junior just in time before the parson can marry them. From this point on the Yellowhammers try to keep Moll under lock and key until she is to be wed to Sir Walter. Yellowhammer says, ‘‘In the meantime, I will lock up this baggage, / As carefully as my gold.’’ With some help, Moll escapes again but is literally dragged back by her mother. Feigning a fatal illness, Moll "dies."

Her parents are so caught up with trying to marry Tim to the Welsh gentlewoman that they do not attend the funeral where Moll and Touchwood Junior rise from their coffins and are happily married. The parson says, "Hands join now, but hearts for ever, / Which no parent's mood shall sever.’’ However, the Yellowhammers's "mood" is surprisingly calm and they support the marriage since Sir Walter has proven to be a debtor and is in prison and because they just found out that they have had Tim married to Sir Walter's prostitute. Yellowhammer says, ‘‘My poor boy Tim is cast away this morning, / Even before breakfast: married a whore.’’ Tim is also distraught, until his mother reminds him of his own words, saying, "You told me once, by logic you would prove / A whore an honest woman, prove her so Tim.’’ Tim accepts the challenge, but his new wife beats him to it, saying, ‘‘Sir if your logic cannot prove me honest, / There's a thing called marriage, and that makes me honest.’’ Thus, both marriages turn out happily.

Sex
Besides references to marriage, the play is saturated with sex, most notably extramarital affairs. Many of the male characters in the play have engaged in extramarital affairs and so have some of the women. In the seventeenth century when a man slept with another man's wife, he was said to have cuckolded the woman's husband. Cuckoldry, which was depicted by multiple horns on the cuckolded husband's head, was often used to provide humor in plays like this. In the play, two men, Mr. Allwit and Sir Kix, are cuckolded. Mr. Allwit is aware of his cuckolding and allows it to happen, since Sir Walter pays for all of the Allwits's expenses in return for the privilege of sleeping with Mrs. Allwit. Allwit says about Sir Walter,"He gets me all my children, and pays the nurse, / Monthly, or weekly, puts me to nothing.'' In fact, the affair between Sir Walter and Mrs. Allwit is so strong that Sir Walter is jealous of Allwit. Allwit says, ‘‘I may sit still and play; he's jealous for me—/ Watches her steps, sets spies—I live at ease.’’

Sir Kix, on the other hand, is unaware of his cuckolding although he unknowingly alludes to it at times. For example, in one passage Touchwood Senior, a very fertile man who plans on impregnating the barren Lady Kix—and attributing her pregnancy to the fake fertility drink that he sells to her husband—asks Sir Oliver if he remembers their deal. Sir Oliver says, ‘‘Or else I had a bad head.’’ This comment, which can refer to Kix's memory, could also be taken by others to refer to the horns that Sir Oliver is about to gain through his cuckolding. Money
Besides marriage and sex, the characters in the play obsess about money. By marrying Moll, Sir Walter will get two thousand pounds in a dowry. Although it appears that he has enough money, the audience finds out at the end that he has been having a hard time paying his bills. As Yellowhammer notes, Sir Walter ‘‘lies i'th' knight's ward now.’’ The knights ward was a special section in debtor's prison that was devoted to knights. Yellowhammer further notes, ‘‘His creditors are so greedy.’’ So, while in the beginning it appears that Sir Walter is marrying Moll because he is interested only in marrying a virgin, at the end the audience can see that he also needed the dowry money to settle his debts. Many of these debts were probably gained from trying to support the Allwits. Through his long relationship with Mrs. Allwit, Sir Walter pays for the children they have, as well as all of the Allwits' living expenses. This certainly helps to drain his funds. As for the Allwits, in the end they use the property and possessions that they have gotten from Sir Walter to better their position in life. Allwit says, ‘‘We are richly furnished wife, with household stuff.’’ Mrs. Allwit suggests that they ‘‘let out lodgings then, / And take a house in the Strand.'' In other words, they are going to rent out their house in Cheapside and use the money to buy a house in the Strand, the fashionable part of London.

Touchwood Senior and his wife also worry about money, since his extreme fertility keeps creating children they cannot afford to raise. However, after he dupes Sir Kix into believing that it was his fertility water—and not Touchwood Senior's affair with his wife—that got Lady Kix pregnant, Sir Kix offers to take care of whatever children Touchwood Senior has. Kix says, ‘‘Be not afraid to go to your business roundly, / Get children, and I'll keep them.’’ After this point, Touchwood Senior and his family no longer have to worry about money.