When bachelor Walter Davis is set up with his sister-in-law's pretty cousin, Nadia Gates, a seemingly average blind date turns into a chaotic night on the town. Walter's brother, Ted, tells him not to let Nadia drink alcohol, but he dismisses the warning and her behaviour gets increasingly wild. Walter and Nadia's numerous incidents are made even worse as her former lover David relentlessly follows them around town.
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Ten years after their divorce, Jane and Jake Adler unite for their son's college graduation and unexpectedly end up sleeping together. But Jake is married, and Jane is embarking on a new romance with her architect. Now, she has to sort out her life—just when she thought she had it all figured out.
Frances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in the Italian countryside, she begins to piece her life back together in unexpected ways.