As plenty of sex comedies have proved, sex acts can be hilarious when attempted by the inexperienced. The awkwardness is overwhelming, and the trick is to find the comedy rather than just making the audience uncomfortable at watching a teenager fumble through dry humping. The To Do List follows its close relative American Pie in pressuring its uptight protagonist to achieve sexual adequacy, but the “twist” is that the teenager is a woman because hey! Women want sex too! Despite writer-director Maggie Carey providing a welcome gender swap for the genre, the picture is surprisingly tame until it occasionally manages a sneak attack with some of the most shocking gross-out gags in recent memory. Unfortunately, the overbearing 90’s setting and an unfortunately miscast Aubrey Plaza undermine the sympathy we’re supposed to feel towards our protagonist.