Brandy Clark has spent all of high school meeting every challenge and then exceeding it – only to find herself jeered offstage while accepting her valedictorian’s honors.

Unnerved by the idea that she’ll enter college improperly prepared, Brandy makes a list of sexually charged shenanigans she intends to engage in before the summer’s up. As it turns out, accomplishing everything on The To-Do List may end up being the toughest thing Brandy has ever done.

Written and directed by Funny or Die veteran Maggie Carey, The To-Do List stars Aubrey Plaza (Safety Not Guaranteed), Alia Shawkat (Arrested Development), and Scott Porter (The Good Wife). The movie also features a bevy of cameos by comedy fixtures such as Donald Glover (Community), Bill Hader (Turbo), Andy Samberg (Hotel Transylvania), and Christopher Mintz-Plasse (Kick-Ass 2).

The second red-band trailer for The To-Do List takes a rather more traditional format than the first, showing off the film’s plot and raunchy comedic style. There’s no denying that much of the film feels rather familiar, mining the same vein of sex comedy as American Pie. That said, the female-centric perspective definitely lends a fresh air to the proceedings.

Given the first trailer‘s emphasis on the film’s release date, it’s curious that The To-Do List has been moved from its original Valentine’s Day release to late July. This doesn’t necessarily reflect poorly on The To-Do List‘s quality – rather, it may indicate that the film’s content may have convinced executives that it wasn’t a fit for a release date saved for more traditionally romantic offerings. We have a month to find out whether the move was weighted in The To-Do List‘s favor.

The To-Do List will open in theaters on July 26th, 2013.