‘When Harry Met Sally’ was released in July 1989 and just over 30 years later, we can still see its impact on pop culture and the world of romance. I, for one, would argue that it’s the blueprint for all romantic comedies that came after it.

From it’s quotable one-liners, the autumnal NYC scenery, to the iconic Carrie Fisher – here are 5 reasons why ‘When Harry Met Sally’ is the perfect Romantic Comedy.

5. The main characters are nut-jobs, but in the most endearing way possible

‘When Harry Met Sally’ opens in 1977 when the title characters are forced to take an 18-hour road trip from Chicago to New York City. Almost instantly, their characters clash.

Harry is the over-sexed pessimist who uses humour to guise his sadness. And Sally is the romantically naïve optimist who’s in the dictionary next to the phrase “high maintenance”.

Billy Crystal isn’t an impossibly dashing romantic lead. He looks like a guy you’d walk past on a street. If you had given that script to the wrong person, Harry would’ve been absolutely miserable. But Crystal was able to soften the character’s cynicism with charm.

Sally’s anal retentiveness isn’t a quirky quality likened by manic pixie dream girls. When she carefully analyzes every vegetable she pulls from the salad bar, and demands the ice-cream be beside the pie, not on top – it’s just who she is, and while easily maddening, Meg Ryan makes it endearing.  

4. The film feels like a warm cup of Autumn

When I think of autumn, I think of the famous scene where Harry and Sally are strolling through a golden brown Central Park, with Sally wearing a grey bowler hat and tweed pants, and Harry in a brown leather jacket.  

Some of my favourite parts are the ones where the two characters are wrapped in blankets in their own separate beds, talking on the phone while watching the same show. While the film itself is aesthetically cozy, their conversations bring another sense of comfort, like the kind you feel when you talk to that person who is always willing to listen to your endless problems and musings.

Autumn is also the season of transition, and it just so happens to be the point in the film where the title characters feelings for one another change. I mean, who wouldn’t want to fall in love to Harry Connick Jr’s big-band/jazz soundtrack?

At the end of the day, ‘When Harry Met Sally’ is the quintessential autumn movie. It tastes like a warm cup of apple cider, feels like a thick, knit sweater, and sounds like crisp leaves crunching under our feet. It’s as bittersweet as unrequited love.

3. Carrie Fisher… need I say more?

When someone says Carrie Fisher, most people think of Princess Leia, and I mean… I do too. But what quickly follows is her role as Marie, Sally’s best friend in ‘When Harry Met Sally’.

Rom Coms just couldn’t get the best friend and B-romance right after Carrie Fisher perfected it in this film. She just set the bar too high.

Marie is a one-liner machine. Her romance with Harry’s best friend juxtaposes the title characters’ 12-year long stint of unrequited love as they almost immediately tie the knot. Marie and her partner coach their friends through romantic crises and turn to one another, grateful that they found a stable partnership while their peers are suffering in singledom.

It takes an incredible actor to steal the show as a side character, and Carrie Fisher does just that.

2. The story and script are timeless

Nora Ephron’s ability to write believable women and believable relationships with such sincerity is exactly what got her the Oscar nod for ‘When Harry Met Sally’.

The dialogue is witty and realistically depicts life and dating in 1980s New York City. The amount of iconic scenes and quotes the movie contains is remarkable, including the infamous fake-orgasm scene famously followed by “I’ll have what she’s having.”

While each character is fully developed, Harry and Sally are stripped of most things except for their relationships with one another. Their personalities are revealed through conversation, and in contrast with one another. Their love story is grounded by interspersed interviews of actors retelling heart-warming love stories of real-life couples, and ends, fittingly, with Harry and Sally telling theirs.

Despite its curly wired landline phones and shoulder pads, these are the things that make it feel timeless.

1. The romance is a perfect slow-burn

So many romantic comedies condense the romance into one night or a week. The thing about romance is that the longer it swells up, the sweeter the release is (if you know what I mean.)

‘When Harry Met Sally’ spans over 12 years. We get to see them grow up, mature and make mistakes. The story unfolds through low-stakes hangouts and well-written conversations that take place during walks against the backdrop of autumnal Central Park. They spend a day at the MET, banter in silly voices, and eat sandwiches at Jewish Delis.

When Harry and Sally start realizing they have feelings for one another, it feels so organic and real. You feel like their friends who so obviously know that the two are meant for each other but just can’t get over their own reservations. It tugs at the heartstrings, the only way a perfect romantic comedy can.

Alannah Link

Alannah is a writer whose vivid self-awareness often veers into self-consciousness. She can be found either watching the latest A24 flick, spending too much money at the local bookstore, or curating a thematic Spotify playlist.

Check out Alannah’s ‘When Harry Met Sally’ Spotify playlist here: jewish deli dates & witty banter

Blog: TheCrookedFriend