Overachieving actress, Rebecca (Moore), must come to grips with her failing marriage to stay-at-home dad, Tom (Duchovny). While Rebecca's slacker brother, Tobey (Billy Crudup), can't seem to commit to his aspiring-novelist girlfriend, Elaine (Maggie Gyllenhaal). As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.

Nick Flynn, in his 20s, hasn't found his place in the world yet, but hopes to be a writer. Around the time he takes a job at a homeless shelter in Boston, his father, Jonathan, who considers himself a great writer and who hasn't see Nick in years, abruptly makes fleeting contact. A few months later, the down-and-out Jonathan shows up at Nick's shelter and becomes a resident. This disorients Nick; he doesn't handle it well, compounded by Jonathan's belligerent behavior. Nick's memories of his mother, his budding relationship with a co-worker, and his own demons make things worse. Can anything improve? Is he his father's son? Written by jhailey@hotmail.com