Valentine is the eldest son of Sir Sampson Legend and a gentleman by birth. Deeply in debt due to his extravagant spending, he locks himself in his chamber to escape his creditors. He relies on reading ancient philosophy to cope with his confinement. He believes his newfound poverty might inspire love in the wealthy Angelica, forming a sharp contrast to the pragmatic views of his servant and friends.

Angelica is a wealthy young woman of independent means. Because she possesses a great fortune of her own, she operates free from the parental dependence that limits other characters in her social circle. She maintains a shrewd, emotionally reserved demeanor, keeping suitors like Valentine guessing about her true feelings while she observes their motivations.

Sir Sampson is the dictatorial, pragmatic father of Valentine and Ben. He views family relationships in highly transactional terms, believing his status as a father grants him absolute authority over his sons. He offers to pay Valentine's debts only if Valentine signs over his inheritance to his younger brother, establishing a bitter conflict over duty and wealth.

Tattle is a worldly gossip who treats love and seduction as mere games. He frequently brags about his affairs with high-born women, though he falsely claims to keep their secrets. He embodies the cynical high society that Valentine frequently avoids, preferring deception and manipulation over honest connection.

Ben is Sir Sampson's younger son, a sailor by profession. He possesses a rough, unpolished manner that embarrasses his father but reflects a straightforward honesty absent in high society. Because he has a naval profession, he holds a degree of financial independence that allows him to speak his mind plainly.

Jeremy is Valentine's pragmatic servant. He serves as a voice of reason, constantly warning his employer about the consequences of his extravagant spending. He holds a cynical view of Valentine's social circle, recognizing that fair-weather friends abandon those without wealth.

Scandal is a friend of Valentine who relishes misbehavior and games of seduction. He holds a thoroughly cynical attitude toward love and women, firmly believing that Valentine's romantic pursuit of Angelica is hopeless. He actively looks for opportunities to manipulate others for his own amusement.

Foresight is an older man who firmly believes he can predict the future through astrology and omens. Despite his claims of great insight, he is highly gullible and frequently mocked by the pragmatists in his social circle. He relies on astrological charts to govern his decisions, representing a worldview where fate supersedes personal agency.

Miss Prue is Foresight's daughter, initially characterized as an innocent, simple girl ignorant of worldly ways. Her father intends for her to marry the sailor Ben. She quickly falls under the influence of cynical high-society characters who instruct her in the arts of deception and evasion.

Mrs. Foresight is Foresight's wife and Mrs. Frail's sister. She engages in affairs while maintaining a facade of propriety. She actively manipulates the younger, more innocent characters, participating in schemes to redirect Miss Prue's affections away from her arranged match.

Mrs. Frail is the single sister of Mrs. Foresight. She views marriage purely as a transaction to secure her own social and financial standing. She strategizes to align herself with whichever man holds the most wealth, rapidly shifting her attentions based on inheritance rumors.