When Aiden invites Billie over to Ed's and his apartment, Billie is incredibly happy, until Cheryl reminds her of what a guy's apartments looks like. Billie decides to go through with it anyway, but keeps a back-up plan just for safety. Meanwhile, Ed and Aiden have to clean up the apartment, which is a big mess at the moment. After being horrified to see his apartment, Aiden unknowingly neutralizes her back-up plan and Billie is forced to sleep over. In the middle of the night she is shocked and calls Cheryl and begs her to come to her rescue.
When Billie is invited to her old friend's Denise's wedding, she wants to bring Aidan, but Phillip demands he work the wedding dinner. In order for Aidan to mingle with the guests so they can get to know him as a person, not as their table server -- a situation complicated by the mistaken seating of Lewis at the same table -- a desperate Billie decides to take over his waiter duties and creates muted chaos, climaxed when she accidentally knocks Aidan into the wedding cake. Meanwhile, Cheryl has complained that she always gets seated next to a loser at weddings and winds up having to tell him she's gay in order to get rid of him. This time he's handsome, witty, and a doctor, so guess what happens?
Billie and Aidan jump through hoops to find each other the perfect gift after learning their birthdays are only three days apart. Three days and 10 years, that is. Billie winds up selecting dozens of possible gifts; and to make things worse, Billie's ex Lewis seems to have come up with the ultimate present.
Billie, a 33-year-old book editor, leaves her predictable lawyer husband and moves into a Chicago hotel to quietly and deliberately take stock of her life. But when Aidan, a handsome and carefree 22-year-old room-service waiter, walks into her room -- and her life -- Billie quickly finds herself thrown into a steamy and "forbidden" affair. Now the problem is how to get their friends to accept their relationship without characterizing is as "older woman/younger man."