Waythorn is a man of business who marries Alice Varick, a woman who has been married and divorced twice before. He is described as dull and attracted to his wife for her high spirits. He seems impressionable and easily swayed, as he is won over by his wife's charms and does not inquire fully into her past before marrying her. He assumes that her first husband, Haskett, is a brute, and he at first believes that his wife is not to blame for her two failed marriages.

Though he first feels conflicted about allowing Haskett to visit his wife's daughter, he gradually gives in and even admires the man for his attentions to his daughter. Waythorn also comes to represent Varick, his wife's second husband, in a business transaction. Over time, his reluctance to deal with these men fades, and he seems to find them preferable to his wife. He is weak in his convictions and allows himself to accede to what is comfortable for his wife.

Mr. Waythorn is, overall, a conventional person who supports social norms and prefers to avoid conflict. He also considers himself broad-minded in that he comes to love and marry Alice although she has been twice divorced. Because he also realized that his life was as unfulfilling as it was uneventful, he is drawn to a woman with a very different temperament. Waythorn’s limited experience with women has left him somewhat naïve, however; he tends to see a pretty wife as an ornament. When he and Alice marry, he does not anticipate the role of Haskett, her daughter’s father, in the child’s life. He also has an exaggerated sense of professional duty, which leads him to agree to serving as a financial adviser for Varick, Alice's other ex-husband.

The internal conflicts within Waythorn far outweigh the external conflicts with either his wife or her two former husbands. He has difficulty reconciling his genuine affection for Alice with his jealousy over her continued dealings with the exes. Waythorn cannot retreat from his commitments or change his fundamentally even-keeled, fair temperament, but he does recognize the harm that jealousy is causing both him and Alice and, by the end, settles into the role of a sympathetic partner.

Mr. Waythorn is an investor in New York who works with a partner who handles the investment affairs of Alice Waythorn's second husband Gus Varick. Waythorn normally leads a quiet "gray" life colored only by his intense sensibilities, which is one reason he was drawn to Alice, who is the opposite of him, and asked her to be his wife.

Waythorn is a moral and ethical man of rational and reasonable temperament and bearing, not quick to find fault or express ill will or rancorous feelings, as is illustrated when he sees Alice talking to Mr. Varick (husband number two) at a ball. He is eminently fair and just as is illustrated by his willingness to allow Mr. Haskett (husband number 1) into his home to visit the sick daughter Haskett shares with Alice.

Waythorn's conflict are three fold. His first conflict is that he has the real conflict of coming up against the realities of his wife's broken but apparently not hostile previous marriages--or, more specifically, coming up against the men from those marriages. He finds himself in embarrassing situations and wonders if Varick (No. 2) had ever found himself in such situations with Haskett (No. 1). His second conflict is with Alice who wants a mild version of having her cake and eating it too (if you save your cake, you can't eat it) by having amiable contact with her previous husbands but not letting Mr. Waythorn know she is. His third conflict is personal: What is the ethical way to behave when brought face to face with (1) an illusion you no longer believe in and (2) tea with your wife's former husbands served by your wife in your sitting room?