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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.

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?

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.