J.C. casually wishes she was a man, so she could see how the other half lives. When she wakes up the next day, she finds her wish has come true, and spends her day noticing all the differences.
Charlotte makes several mistakes in J.C.'s schedule and then apologizes for being so tired and inattentive. J.C. later discovers the source of Charlotte's problems when she attends a local comedy club.
When J.C. passes out after her gym workout, she awakens to see the handsome Dr. Kevin Atwater back in her life. The good doctor is no longer engaged, and asks J.C. out to dinner.
J.C. needs to find a new nanny for Elizabeth when Helga quits after she is offered a better job. She quickly regrets letting Helga leave, as the procession of inappropriate replacements seems relentless.
This episode contains multiple flashbacks as J.C. frets over her bad luck in relationships, just as she has met a new guy. Her first failure was as an eight year-old spelling-bee contestant who spelled "xylophone" correctly after her boyfriend missed it.
J.C. ensures that Santa goes all out for Elizabeth, as they celebrate their first Christmas together. Fritz is also celebrating, but under very different circumstances.
J.C.´s boss asks her to give a presentation to secure a $2 million account. She and Arlene arrive at the company's headquarters, only to discover that it is an all men's "club".
Elizabeth has a play date with her friend Jamie. When Jamie and her parents show up, J.C. becomes nervous because they look "dangerous." She reluctantly lets Elizabeth go, and then spends all day worrying instead of relaxing.
J.C. reflects on her busy life as she becomes more and more concerned that she will meet the same fate as her father. He died from a heart attack, the result of a stressful life.