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.""
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 for her -- an expensive bracelet, which Billie and Cheryl assume, came from Aidan. Meanwhile, Aidan panics when Ed derides his impulsive ""perfect"" gift for Billie: a blue catcher's mitt.
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? Best line is Cheryl to the redheaded, tuxedo-clad Ed: ""You look like a penguin with its head on fire.""
Aidan's big debut at an open-mike night hits a flat note when Billie storms the stage to cover her beau's rusty singing pipes. Meanwhile, Cheryl plays the age-game with a younger man who turns out to be a guy she met a long, long time ago; and Ed poses as a virgin to land a lady of the same virtue.
Hoping to meet a famous author, Aidan poses as Billie's cousin, only to find the literary giant has a little thing for Billie. Meanwhile, Ed does an about-face when he enrolls in beauty school to stay in the country.
Billie and Aidan's one-month anniversary turns into a night to forget when their gifts to each other land them at separate places. Meanwhile, Ed and Manuel convince Aidan to strike a pose -- naked -- to earn extra cash.
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.
Aiden's ex-girlfriend returns from Europe, forcing Aiden to admit that he never really broke up with her before she left.
When Billie finally moves her things out of Lewis' house, he kisses her. Unfortunately, Aiden witnesses the event.
Billie goes back to work and soon discovers how hard it is to schedule even a quick lunch with Aiden.
Lewis complains about the way Billie and Aiden care for dog Gordon.
The couple seriously considers the possibility of buying a house.
Billie Learns Aiden is applying to law schools and pulls strings to get him in. Meanwhile, Cheryl gets revenge on an old friend who steals boyfriends.