The film's subject of an older woman with a younger man is close to writer-director Bart Freundlich's heart - his wife Julianne Moore is 10 years older than he is. Conversely, lead actress Catherine Zeta-Jones is also 25 years younger than her husband, Michael Douglas.
Joanna Gleason's character Roberta refers to previously being employed at Ralph Lauren. A reference to her part in the TV show, Friends (1994) in which she played Rachel's boss at Ralph Lauren.
Originally scheduled for a US cinema release until the film's distributor shut down. The film ended up going direct to DVD over a year later.
The actor who play's Harry Finklestein, Aram's father is Art Garfunkel. He is best known by everyone as being in the music rock duo, Simon & Garfunkel. One of their hit songs was "Mrs Robinson (1967)," which was about an older woman falling for a young man, which was used in The Graduate (1967), which has the same plot as the song.