1. Harvey Nash is certainly not the kind of man with whom most women would choose to become involved. Yet despite his oily loyalties, arrogance, and opportunism, he charms nearly all of the characters, to some degree, at some point in the novel. How does Harvey—now called Nash—make his way into Adele, Kathleen, and Lois' good graces? How does he maneuver his way into the arms of an intelligent, beautiful, and successful woman like Cynthia? What is it about this type of man that continues to be attractive to women and despite their better judgment they continue to succumb to his charm?
2. To what extent does the notion of good manners prevent the Dobbins from getting rid of Nash? To what extent are all three—on some level—curious about him?
3. How does fear threaten each female character's ability to act on her attraction to others? How does Nash confirm their fears? How does his behavior play a role in diffusing their fears?
4. How are the Dobbin sisters' loyalties to one another threatened by Nash's reasserting himself into their lives?
5. What role does Richard Dobbin play in the novel?
6. Perhaps one of the most hilarious scenes in The Ladies' Man is Cynthia's big party for Nash. How do the events leading up to the big night infuse each guest's entrance with tension? How does dialogue up the ante once the party begins?
7. How does Kathleen handle Cynthia's feelings for Nash? How does Kathleen and Cynthia's friendship effect the course of the novel?
8. Nash performs one notable and noble act in The Ladies' Man: he makes Marty Glazer jealous. What prompts this act of selflessness? Is it completely selfless? If not, how does his gesture endear him to us nonetheless?
9. How does Elinor Lipman keep us interested in so many different characters over the course of the novel? Were there characters you cared about more than others?
10. How do the characters in The Ladies' Man highlight different ways we approach—or shrink from—love today? What aspects of modern American culture make the pursuit of romance more difficult than in the past? What aspects make it easier?
11. Comparing The Ladies' Man and The Inn at Lake Devine
1. Author Anita Shreve has written, "I have not read an American writer who can do what Elinor Lipman does: take a poignant situation and transform it, in a moment of instant recognition, into something as wryly perfect as a New Yorker cartoon." What issues does Elinor Lipman leaven with humor in both The Inn at Lake Devine and The Ladies' Man? Why does humor work well in highlighting these issues in particular?
12. 2. Food plays a powerful role in both The Inn at Lake Devine and The Ladies' Man. How do characters use food to nurture themselves and each other? How do they use food to hurt themselves and each other?
13. 3. Both The Inn at Lake Devine and The Ladies' Man contain moments of tragedy. How are these moments treated in each novel?
14. 4. Which plot twists in each novel surprised you the most? Were the surprises believable? If they were not altogether believable, did it matter to you? Why or why not?
15. 5. In both The Inn at Lake Devine and The Ladies' Man, Lipman's characters find themselves in awkward social situations—for example, Natalie's confrontation with Mrs. Berry, Adele's discussion with Cynthia.) How do Lipman's heroines behave in these exchanges? Why do you suppose Lipman chooses to place them in these situations?
16. 6. Love can seem elusive—especially to intelligent, independent women over thirty. In a 1986 article that rocked the nation (and prompted a pointed response in Susan Faludi's Backlash), Newsweek asserted that a forty-year-old unmarried woman was more likely to be killed by a terrorist than to make her way to the altar. How difficult is it to find love in modern America? How do Elinor Lipman's novels—charming, realistic, intelligent—restore our hopes?