Harry and Sally drive from the University of Chicago to New York City, during which they discuss their many deep and enriching friendships with people of different genders. “I respect the opinions and achievements of all people without sexualizing them for my own personal conquest,” Harry tells Sally. “Also, gender is a construct.”
During a pit stop, Sally tells Harry about her ex-boyfriend, Sheldon. Harry doesn’t make any assumptions about their sexual history. Sally blushes to herself, thinking of her exploratory, adventurous college years, where she identified exactly what she did and didn’t like with a partner. She does not tell Harry this once included her friend and his current girlfriend, Amanda.
Sally tells Harry she’s going to New York to pursue journalism and Harry is supportive of her career goals. “I know you know this, but don’t let them pay you any less than what you’re worth,” he reminds her. “Even though you have a degree from a competitive school, I understand I have a natural advantage in my career because I’m a cis white hetero man, and I would hate to see your talent be undervalued.”
Over ten years later, Harry complains to Sally that his date didn’t laugh at his joke about Ethiopian food. “Well, what you said was pretty insensitive and takes a stereotypical Western view of a non-white country,” Sally informs him, before asking for his date’s number so she can hang out with her later without him.
Harry and Sally have a heated discussion at a diner about enthusiastic consent. “I recognize it’s not your place to teach me,” Harry confesses. “But now I understand how to listen better to my partner’s needs. I recognize orgasms happen in many different ways, and sometimes a sexual encounter doesn’t even have to have a goal.” A woman seated nearby orders whatever she damn pleases without worrying what anyone else thinks.
Harry encounters his ex at a specialty toy shop, and thanks to his time spent in therapy, has resolved his anger issues and is genuinely happy for her. Harry, Sally, Helen, and Ira finish singing “Surrey With a Fringe On Top” in perfect harmony.
Harry and Sally finally sleep together, and decide to have an honest, emotionally mature discussion about their feelings at Marie and Jess’s wedding. “Let’s not have this conversation back here in the kitchen,” Sally says as she leads Harry outside. “These people are doing a lot to cater this large wedding party and we shouldn’t impose our drama in their workspace.”
After their fight, Harry leaves Sally just one heartfelt message that says, “Hey, I’m sorry I’ve been pushing my emotional labor onto you, and I’ll be right here when you’re ready to talk, but otherwise, I’m going to respect your space. Don’t worry, I won’t pressure you with any public grand gestures or anything.” Sally takes her time to respond, especially since she’s so busy writing investigative pieces on the #MeToo movement.
Sally has an epiphany, and tells Harry how once you realize what you want for the rest of your life, you want the rest of your life to start as soon as possible, and that’s why she applied for that international fellowship and is moving to Rome. As a parting gift, she buys Harry a wagon wheel coffee table.