When Brooke's former high school classmate Anna Wheeler approaches Brooke and Tracy in the bar, Anna mentions that she and her husband have recently seen the play Other Desert Cities, which began previews at the Booth Theatre on October 12, 2011 and closed on June 17, 2012. If the film occurs during Tracy's first semester of college and culminates with Thanksgiving dinner with Brooke at Veselka, then the film would occur in fall 2011. However, when the would-be stepsisters walk through Times Square, a marquee for the revival of Annie is visible. The most recent Broadway revival ran at the Palace Theatre from October 3, 2012 (first preview) to January 5, 2014.
There is a scene that Tracy is walking on campus with lighted trees on the background. It is actually on the College Walk of Columbia University. And those trees will not be decorated with lights until mid December for the Christmas. But the story happens before Thanksgiving.