In 1989, I was a divorced woman with a ten-year-old son and an eight-year-old daughter. It was not easy to date. I had “baggage.” I was cynical and hopeful every time I went out. Family and friends surrounded me, but I was always looking for love. I remember the first time I saw WHEN HARRY MET SALLY. I was struck by the infinite possibility that my true love was still waiting to be found. The interviews of the older couples and how they discovered each other gave me hope. Watching a strong, confident woman not be afraid of who she was and what she wanted fueled my ego not to give up. I imagined myself with someone I could banter and chatter with, just like Sally. Her clothes, hairstyles, and especially her hats renewed my energy and quest. I wanted to find someone I could share common interests, learn something new every day, and be myself in all my “controlling” glory. I recognized the honesty and truth behind being able to be “best friends.” I longed to “know” someone in such detail as Harry knew Sally. I own this film on DVD and have rewatched it countless times. My Dad’s name was Harry, and he and my Mom’s love story could have been one of those loving interviews. They were together for 64 years. I yearned for what they all found and had. WHEN HARRY MET SALLY influenced me more than I realized. It is one of the sweetest rom-coms of all time. 

Rob Reiner fashioned WHMS after his depressed, neurotic, newly divorced life. As director and producer, he teamed up with Nora Ephron, the screenwriter, to create a different type of love story. Sally was fashioned after Nora and her precise, specific way of ordering food. Harry was a chip off of Rob’s personality and real-life friendship with Billy Crystal. Harry and Sally’s conversations always mirrored how Billy and Rob spoke to each other. Together they delved into whether a man could be just friends with a woman. Is this possible? Take sex off the table and let their relationship play out. Their first draft together did not end happily ever after, but they soon knew they had to make changes for audiences to fall in love with the couple. 

WHEN HARRY MET SALLY is a simple premise. Two people meet while sharing a ride from Chicago to New York. Harry (Billy Crystal), and Sally (Meg Ryan), appear to be opposites and are destined never to meet again. Not so, even if he spit grape seeds on her car window. He declares he can’t be friends with her even if she is attractive. Men can’t stop thinking about sex when in a relationship. Harry challenges her when she disagrees. He believes it is because Sally has never had great sex. He says this as they are walking into a diner. Meg immediately shouts, “I have had great sex,” so loudly that the entire restaurant stops talking and stares at her. A humorous foreshadowing moment. Years pass, and it isn’t until ten years later that the “relationship” changes. They become best friends and hang out all the time. There are too many funny moments during this film to mention them all. Mailing letters into a city mailbox, watching movies together or in their separate apartments “together” (with a split screen) are hilarious. Harry is such a “groaner.” They are indeed “two peas in a pod” and never realize their “love” for each other for several more years. The two of them even have to separate to make the final connection. Whew! What a journey. Sally is indeed “high maintenance,” but she doesn’t know. 

Working with Billy Crystal always led to improvising. The scene at the museum where Harry insists Sally “talk like this” was a master class in improvisation. “I would be proud to partake of your pecan pie” was not in the script. The final interview of the movie with Harry and Sally was totally created “live.” Funny, quick, creative, and insightful. The best, most iconic scene took place in Katz’s Deli. The conversation quickly turned to Harry’s love life and how he had no idea women sometimes fake orgasms. Not with him, he declares. Sally challenges him that he would not know a real one from a fake. Then she proceeds to have an orgasm right there for all the Deli’s patrons to hear. It is hysterical. The cuts to people’s reactions as she moans and screams “yes, yes, YES” will have audiences rolling on the floor uncontrollably laughing. The next line is forever embedded in movie history as well as on a plaque glued to the table in real life. Estelle Reiner (Rob Reiner’s mom) played an extra and calmly told her waiter, “I’ll have what she’s having!” This was Billy’s suggested ad-lib for her, and the only line Estelle will ever speak in the movies but is forever remembered. Meg Ryan had to do several takes of that scene. I would not have been able to keep a straight face. 

Another scene on WHMS took 61 takes to get perfect. Rob had to set three sound stages for the dialogue when Harry and Sally “do it” and then call their friends to share the news. Marie (Carrie Fisher), and Jess (Bruno Kirby), had to be in sync with Meg and Billy talking over each other and during the final action of slamming all four phones down in order. Finally, cameras had all actors on screen at the same time. Amazing, magical, movie moment. 

The New York City cinematography was spectacular. They showcased the four seasons in all its glory. The City locations almost became another character in this film. The costumes from the ’80s and 90s were spot-on, along with the Farrah Fawcett hairstyle. Everyone wanted that look. The music got you in the mood for romance from the opening notes of the movie. Harry Connick Jr. created the special arrangements. “Oh, IT HAD TO BE YOU.” 

This wonderful movie is especially significant at this time of year. Harry and Sally share two very important New Year’s Eve celebrations. One, as great friends, and the other created the “burning” end to this marvelous movie. Harry asks what the meaning is behind the words to the song AULD LANG SYNE.  This is the melody everyone sings in unison at midnight. They discuss and finally Sally says, “I think it’s about old friends.” Harry knows she’s right because “when you realize you want to spend the rest of your life with someone, you want the rest of your life to start as soon as possible.” Sigh. Now those words are what every couple longs to hear especially on New Year’s Eve.

WHEN HARRY MET SALLY…is smart, entertaining, and heartwarming. It pulls at your gut and makes audiences yearn for a romantic, silly, caring, kind, friend who is the forever, love of your life. It is ranked sixth on AFI’s list of the ten greatest “Romantic Comedy” genre. Everyone can see a bit of themselves in Harry and Sally. We are all searching for a special connection. Harry keeps us grounded, and Sally makes us hopeful. The two of them together are unforgettable. “I knew the way you know about a good melon.” It is a classic to be treasured and enjoyed forever.

WHEN HARRY MET SALLY… is available to stream on HBO MAX. 

Esta Rosevear

Esta Rosevear has been a Theatre Arts teacher and director for 35+ years, published Children’s author of the Rebecca series, and is passionate about playing her violin, walking, gardening, and reading murder mysteries.

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