Plan B (1997)

Plan B is a "Big Chill" type comedy-drama set from a typical Halloween to New Year's Eve which follows five 20 and 30-something friends living in Los Angeles whose lives fail to turn out the way they expected. Stuart is a struggling writer trying to make it big with his first novel while working part-time as a waiter. Stuart's roommate/co-worker, Ricky, is a struggling actor who cannot get an acting job and frets about his hair turing gray and meeting the perfect woman. Stuart and Ricky are friends with Jack and Clare Sadler, a couple trying and trying to concieve a baby, but cannot get it done. Finally there's Gina, Clare's younger sister, who cannot stand letting go of her past as well as being alone at family get togethers and tries bringing an assortment of dates to each gathering.