Meet Jess, Robin, Anne, Lilith and Beth…five thirty-somethings living in Chicago and trying to navigate work, men, life and love with humor, intelligence, and – most of all – friendship. Though each woman is very different, and clearly on her own path of discovery, the strength they find in each other makes their individual journeys a little easier. We meet the ladies in flashback at a Valentine’s Day slumber party, establishing the connections between them, and giving us a snapshot of where the women are in their lives. We then move to present day, two years later, and each of the five tells her own story as it happens. Part Sex and the City, part Little Women, with a dash of Slaves of New York (well, Slaves of Chicago, at the very least), Sleeping Over examines relationships both romantic and platonic, (and platonic wanting to be romantic), and looks at all the various configurations of what it means to "spend the night" with someone.
Jess has just returned from a two-year Peace Corps tour in Kenya, and is crashing at the condo of her cousin Mark’s best friend, pediatrician Harrison. Dealing with a return to Western Civilization, her long-divorced parents dating each other again, and the feelings she is trying not to develop for the dashing doctor she is living with, may in fact make her crazy at any moment. Then again, if the doctor reciprocates, she just might be on the road to real joy.
Robin relishes her job as executive sous-chef in a trendy little restaurant almost as much as she relishes her friendship with its owner, Michael. But while Michael may think that their cuddly sleepovers are just friends being affectionate, Robin knows that she wants much more. But how do you make someone who knows you so well look at you with fresh eyes? And if he does, will it spell disaster at work?
Beth and her sister, Anne, have recently opened up a boutique together which is managing to keep afloat in spite of the economy. Beth isn’t really concentrating on much besides the store, fixing up her loft, and playing with her dog Petey when unexpected reconnections with three men from her past throw everything into turmoil. Ex-boyfriend Sasha has decided they should be friends again, as has grad-school lover Eric…all while Beth is in the infancy of a romance with Jeff, a guy she detested in college who has suddenly become the opposite of detestable. It is either an embarrassment of riches, or a nightmare from the tenth circle of hell, and she will need loads of support from the girls to puzzle out her next move.
Anne loves Beth, and Beth loves their working partnership, but the store isn’t Anne’s dream, and while the sisters share almost everything, Anne’s secret desire to go back to school to pursue a career in occupational therapy is keeping her up nights. Lucky for her, these nights are no longer spent alone, after a bizarre series of events brings Chris into her life – and for the first time, Anne knows what it means to be completely swept off her feet.
Lilith has finally returned to her work in theatre after nursing her father during his ultimately unsuccessful battle with cancer. But getting back in the game has her stuck in the worst kind of triangle. While she and boring boyfriend Martin are temporarily "seeing other people," she meets Noah, a deliciously enigmatic actor, for whom she falls head over heels. Problem one, Noah is married. Problem two, Noah isn’t the least bit interested in Lilith, except as a friend. But Jay, on the other hand, is very interested. He is younger, brasher, nothing Lil ever expected to want or need…but nevertheless intriguing. Lil struggles with letting go of the idea of Noah to see if she should be more open-minded about Jay.
There are surprising twists for each of the women, separately and together, including one major disaster which threatens to change their friendship forever. But at the end of the day, five is always a happier number; and sometimes, whoever else you may be sleeping with, sleeping over with your girlfriends can be the best thing to do.
