A mysterious man drops off a $2000 check to cater a small party just when Kate and Allie's business is about to go bankrupt. He returns in their dreams to convince them to appreciate their lives and families by showing them just how bad things would actually turn out if all of their wishes came true.moreless
When an odd man named Mr. Gabriel appears and offers Kate and Allie $2,000 and a job, he asks one additional thing of them -- that they each give an account of their lives. Christopher Murney guest stars as Mr. Gabriel.
Allie's ex-boyfriend Malcolm returns to New York for the opening of his off-Broadway play, which turns out to be based on their romance. He starts dating Kate during his stay, which plays out nearly the same as his previous romance with Allie.
Kate, shaken by Emma's transfer to UCLA and ex-husband Max's recent success as an actor, spends her 40th birthday wondering what she has done with her life and decides to make a drastic change to reconnect with her activist roots.