Kathy is married to Peter. Now she can't help but wonder how things could have been if she had gone out with her old boyfriend, Tom. Being married prevents her from doing that so she asks her friend, Emily, to go to him and see if she can sleep with him then tell Kathy how it was. When Emily tells Kathy that things were awesome, their friendship suffers, at the same time so does Kathy's marriage. Things get even more complicated when Emily learns she's pregnant and she's not certain if it's Tom's or her boyfriend, Elliot.