Aemilia is sister to Valeria and daughter of Fondling and Littlegood. Despising old Dotario, her father's choice of spouse for her, Aemilia promises to make Dotario's life miserable if they wed. As part of a plan, Aemilia weds her true love Careless while he is in the guise of Dotario.
AURELIO
Aurelio is a disinherited older son, brother to the irresponsible Careless. He loves Valeria but cannot win permission to wed her because he is penniless. Spruse nearly destroys Aurelio's faith in Valeria, producing Aurelio's ring that Valeria had lost and claiming that the lady bestowed it as a gift. Spruse admits his lie and helps Aurelio wed Valeria, who has feigned madness and been sent with the disguised Aurelio in hopes of a cure.
BOY
This unnamed Boy announces Spruse has come to see Careless.
CAPTAIN WHIBBLE
Whibble is a poor excuse for a Captain in any institution, for he is out for himself on all occasions. He pretends to befriend Careless and urges the young man to sell his land for ready cash. Later, he and his friends exit a dining establishment, leaving Lackwit with the bill. His true feelings about Careless finally revealed, Whibble eventually weds the Hostess (to whom he is in debt) and becomes himself a Host.
CARELESS
Careless is brother to Aurelio. Though a younger son, he has the fortune of the father because Aurelio has been disinherited. An irresponsible spendthrift, Careless listens gladly to those who advise the sale of his land. He later dons a disguise and learns Whibble's true feelings about him; again disguised, this time as Dotario, Careless weds Littlegood's daughter Aemilia. Careless has learned something about responsibility and honor throughout the course of the play, and he has discovered there are more important things in life than being called "a fine companion."
CROCHET
Crochet is a clown figure. He disagrees with Littlegood's plan to wed Aemilia to Dotario; in helping foil this plan, he sets up a scheme whereby Aemilia weds Careless in disguise as Dotario, thus embarrassing Lackwit who takes credit for accomplishing what he believes to be the match desired by Littlegood.
DOTARIO
Dotario is an old gentleman, uncle of Aurelio and Careless. He plans to wed Littlegood's daughter Aemilia and has her father's blessing although Aemilia strongly resists the marriage. When he discovers that Careless-disguised as Dotario-has wed Aemilia, he agrees to leave his fortune to Aurelio in exchange for everyone's silence about the wedding trickery.
FIDO
Fido is a friend of Aurelio and Careless, eager to help both of his companions. He tries to urge Careless not to sell his land. He also aids Aurelio in delivering Valeria a letter instructing her to feign madness in a plan to unite Aurelio and his love.
HABERDASHER
This unnamed Haberdasher is summoned to help design a new and elegant suit for Careless.
HOSTESS
This unnamed Hostess refuses to serve Captain Whibble and friends. Already she has allowed the Captain to run an unpaid tab, even providing him monies from her own purse. At play's end she weds Whibble.
LACKWIT
Lackwit is the son of the usurer Littlegood, who wishes his son to be scholarly, and Mistress Fondling, who desires her son to learn dashing courtly skills and to sow his wild oats. Eager to become a "brother" to Captain Whibble and company, Lackwit not only is deprived of his hat and cloak but is also left with his carousing friends' bill. He promises to accomplish a fine deed in seeing that his sister marries as his father wishes to Dotario. Instead he is duped into allowing his sister Aemilia to wed the disguised Careless.
LIEUTENANT
This unnamed Lieutenant joins Captain Whibble in trying to deprive Careless of his land and money. He suggests that being a pimp is a most noble profession, and he ends the play by turning tapster in the employ of Whibble, who has turned Host.
LITTLEGOOD
Littlegood is an usurer by trade and is married to Mistress Fondling. He gives in to Fondling's demand that their son Lackwit be allowed to sow a few wild oats; the result is that his son unwittingly brings about the marriage of Aemilia to Careless, when Littlegood would have instead wed his daughter to Dotario.
MISTRESS FONDLING
Wife of Littlegood and mother of Lackwit, Aemilia, and Valeria, Fondling's primary concern seems to be her son. She feels that he has grown sallow with too much learning and wants him to learn "breeding," which includes sowing a certain amount of wild oats.
SEMPSTER
Careless brings in this unnamed Sempster to help in fashioning a new and elegant suit.
SPRUSE
Spruse resorts to chicanery in his wooing of women. He first appears in the play to show a box of unsigned love notes, penned by hire and ready for Spruse simply to fill in a woman's name. Hoping to win Valeria but never planning to wed her, Spruse first claims that Valeria has given him the ring that Aurelio had earlier given her. Forced to confess the truth, Spruse finally aids Aurelio in wedding Valeria.
TAILOR
This unnamed Tailor promises Careless that his new and elegant suit will be ready in three days.
TONY THE DRAWER
Tony is the tapster who presents a bill for thirty pounds to Captain Whibble.
VALERIA
Valeria is the daughter of Littlegood and Fondling, sister of Aemilia and Lackwit. She loves Aurelio but cannot wed him because he has been disinherited. Courted by Spruse, she accidentally drops a ring given her by Aurelio. Spruse finds it and tries to convince Aurelio that she gave it him as a gift, but he is finally forced to confess the truth. Valeria pretends to be mad, and Aurelio-disguised as a doctor and now aided by Spruse-takes her away ostensibly for a cure and weds her.