1.
Stephanie asks herself, “What attracted a thirty-three-year-old, single, unattached, attractive woman, with her own mortgage and car, to a man with the ultimate baggage: a wife, two teens, and a struggling business?” Why do you think she's attracted to a man with so many complications? Have you ever been in her position? What does she see in Robert that makes him so attractive to her?
2.
Stephanie says, “All men lie. But let's be honest, we wouldn't want them to tell us the truth about everything, would we?” She similarly believes that all women lie as well. When is it okay to lie to a spouse or partner? Have you ever lied to your spouse? Can a lie be justified?
3.
As technology changes, so too does the nature of an affair and, indeed, all relationships. Stephanie checks her e-mail and finds an urgent message from Robert. She also gets an instant message from him. How do you think technology has played a role in affairs? Are relationships stronger or weaker now because we are almost always connected?
4.
Stephanie's father advises her that “love is the only thing worth fighting for.” Is love always worth fighting forâeven if it's with the wrong person?
5.
Are you surprised by Stephanie's coldness when she learns about Jimmy's death? Does it make her a bad friend that she did not immediately console Robert? How would you react if your lover's best friend had just died?
6.
Should Stephanie tell Robert she is pregnant with his child or should she keep that information to herself? Why?
7.
Maureen tells Robert that it is time for him to choose between Stephanie and Kathy. Yet, do you think the choice is still his to make? Is it really now the women who are making the decisions in this situation?
8.
When Kathy confronts Robert, she accepts some responsibility for what happened. How culpable do you feel Kathy was? Can you fault her for his affair?
9.
Robert worries that Kathy will spy on him for the rest of their relationship. When trust is broken, how long do you feel it takes for that trust to be rebuilt? Indeed, is it ever possible for trust to be rebuilt? Could you trust your partner if he or she had betrayed you by having an affair?
10.
Kathy wonders if a man and a woman can have a purely platonic relationship. Do you think it's possible? Do you know any male-female friendships that are completely devoid of sexual tension?
11.
Kathy's sister Julia immediately rushes to judgment over their sister Sheila's affair. Have you ever jumped to a conclusion about a relationship before hearing both sides of the story?
12.
When the truth about an affair comes out, women usually side with women and men with men. Have you ever stuck with a friend even though you knew he or she was behaving in an inappropriate manner?
13.
Sheila says, “In an affair, there are no blacks and whites, only shades of gray.” But is that true? Or is an affair always black and white and simply wrong? Where are the shades of gray in Robert's affair?
14.
Robert and Kathy's children are present throughout the book and are a major factor in both Kathy's and Robert's thoughts. We never get to see their side of the story. How perceptive would teenage children be to a situation like this unfolding around them? Whose side do you think they would take?
15.
Until Kathy discovers Robert's ultimate betrayal of lies, she still has hope that they can rebuild their relationship. Can you understand her actions and is she right to fight for Robert even after the betrayal of the affair? Do you agree with her?
16.
At the end of the book, the two women discuss going into business together. Given that they are very alike in many ways (Stephanie has acknowledged that she is a younger version of Kathy), do you think the women would be good business partners?
17.
Statistically, men often have affairs with women who look like a younger version of their present partners. Women never have affairs with men who look like their partners. Why is this, and what does this tell us about the sexes?
18.
Where do you think Robert will be in a year's time? He is about to lose his wife and family, his home, and probably his business. Can he start again or will he end up like Jimmy Moran?
19.
All affairs begin in the mind. But at what point does an affair begin? Is it with flirtation, a kiss that is more than a peck on the cheek, sexual texting or salacious e-mails? Or does the affair really begin the moment the couple end up in bed together?