Bring on the tough stuff. There’s not just one right answer.
- So wait a second… can a man and a woman be friends? Why or why not?
- Both Harry and Sally have some just-short-of-insufferable qualities. With Harry, you might say it's his constant need to turn everything into a joke. Sally, for her part, is a bit of a control freak. Do you think these qualities will counterbalance themselves in a relationship? Are these two headed for wedded bliss or a lifetime of squabbles?
- In what ways do Harry and Sally change over the course of twelve years of knowing each other? Are those changes a result of their friendship, or other forces?
- What do you make of the old couple interludes that break up the movie (and usually indicate the passage of time)? Are those couples meant to be a source of wisdom—or whimsy? What do they add to the movie?
- Quick! Name all the romantic comedy clichés you can find in When Harry Met Sally. Do you think any of these clichés actually began with this movie? In other words, do you see any influences of this movie on more recent rom coms?
- What role does the setting of New York City play in When Harry Met Sally? Could this movie have taken place in, say, Montana?
- We get the romantic part: boy meets girl, boy and girl bicker and flirt for ages, boy gets girl. But what about the comedy part? In what ways is this movie funny? What does it rely on to make you laugh—satire? Irony? Pratfalls? (Probably not pratfalls.)
- Does When Harry Met Sally perpetuate old-school gender stereotypes (the controlling woman, the emotionally unavailable man)? Why or why not?
- What role do Marie and Jess play in the movie? Are they just sounding boards for Sally and Harry, respectively? Could they maybe be foils for our OTP?