When the scene showing Julie Keller's (Jennifer Westfeldt) birthday was shot, it was done so on Jennifer Westfeldt's actual birthday.
Jennifer Westfeldt wanted Jake Kasdan to direct the film, which Jake Kasdan turned down, opted to produce it instead, but was the one that suggested that Jennifer Westfeldt herself directed it.
Kristen Wiig shot most of her scenes on Sundays on account of her occupation on Saturday Night Live (1975).
The dialogue between Chris O'Dowd and Maya Rudolph about their age difference was a rewrite by Jennifer Westfeldt. After casting Chris O'Dowd, the issue of the couple's age difference had to be addressed in the film.