“I think you should wear skirts more. You look really good in skirts.”
- Harry (the one who Met Sally)
While I don’t unreservedly love this film as I once did, this is such a well-written line of dialogue, and it does so much work.
At the end of an afternoon outing to the Metropolitan Museum of Art, Harry and Sally are in the Temple of Dendur. He’s enticed her into speaking in a silly voice, and, still in accent, asked if she would like to see a movie with him that night. She asks the question back and he shakes his head. “Not to repeat, to answer,” he says, still in the silly voice. Turns out, she already has a date for that night. “I was going to tell you about it,” she says, “but I don’t know I just… I felt strange…[] because we’ve been spending so much time together.”
Without missing a beat, Harry asks what she’s going to wear—brilliant (from his point of view). It directs the subject away from his feelings—which we may be starting to suspect—and puts him back in charge of the conversation. It’s a power move, a way of possessing Sally and getting in a compliment before the guy she’s going on the date with has a chance to, but it’s also still praise. To us, it’s sexual enough to confirm, yep, he’s interested, but it’s such tempered admiration—she’s not wearing a skirt when he says it—that it’s almost brotherly. Sally has just shown their friendship’s limits. In his way, Harry is responding by inviting her to further intimacy, and accepting that he’s not eligible for a romantic relationship with her. Sally is hesitatingly pleased, with that inimitable Meg Ryan expression.
In the next scene, she’s wearing a skirt, helping him redecorate his (ridiculously large) apartment, and the pattern for many a hopeful, enabling friendship has been laid out.
