The 12 Most Age-Inappropriate Romantic Pairings in Woody Allen’s Career

In recent years, Woody Allen has been known for his tendency to cast young actresses as love interests for much older men. While his pairings were mostly age appropriate until the early ‘90s (with the obvious exception of “Manhattan”), the creepiness factor has shot upward in recent years, from Larry David romancing Evan Rachel Wood in 2009’s “Whatever Works” to Emma Stone’s recent pairings with Colin Firth and Joaquin Phoenix (although Allen’s latest film, “Irrational Man,” which stars 26-year-old Stone opposite 40-year-old Joaquin Phoenix, is actually pretty tame compared to some of his other outings). Here’s a look at the most egregious romantic pairings from throughout Allen’s career.