The Graduate — 10 Films With Lousy First Dates
Participants: Ben (Dustin Hoffman), a recent college grad in the midst of an aimless summer having an affair with an older woman; and Elaine (Katharine Ross), the daughter of said older woman.
Circumstances: Ben is put up to this by his parents, much to his chagrin (and fury from Mrs. Robinson, his paramour). Elaine has no idea about her mother and Ben, of course, and just wants to meet this interesting fellow she's heard so much about.
What Makes It Awful? Ben is furious, at first, with the whole situation, and what it's going to mean to his affair, which is really the only thing keeping him going at this point. As a result, he drags Elaine around as if he can barely stand her, and ignores her as best he can, until she finally can't take his rude disregard and storms away with tears in her eyes.
Outcome: Ben chases after Elaine to apologize, the two start actually talking, and it turns out they have a lot in common. Before he knows it, Ben is smitten, which leads to the famous end scene of him busting up Elaine's wedding with "the make-out king" and running off with her on a public bus. Only to realize he still has no idea who he or what he wants.