4. Observe & Report (2009)
Leave it to Eastbound & Down creator Jody Hill to play date rape for laughs. Mall cop Ronnie Barnhardt (Seth Rogen) thinks he's hit the jackpot when makeup counter hottie Brandi (Anna Faris) agrees to have dinner with him. In between tequila shots, she pops a couple of Ronnie's Klonopin, rendering her barely conscious by evening's end. But Brandi's lack of mindfulness nor the fact that she's covered in vomit prevent Ronnie from seeing this date conclude the way he hoped it might: under the covers.
Hill softens the blow by having Brandi wake up during the act and urge Ronnie to keep going, implying that she was conscious for the start. Whether Hill's "softening" of the joke bothered you or not says volumes about whether or not we'll hang out with you.