If you have a weakness for romantic comedies (which I very much do), I'm guessing you've already seen the classic Tom Hanks and Meg Ryan movie, Sleepless In Seattle. Penned by the brilliant Nora Ephron, who was behind movies like When Harry Met Sally, You've Got Mail, and Julie & Julia, this 1993 film is arguably the definitive romantic comedy of the '90s, mostly because it revolves around a singularly smart trick: the two romantic leads never properly meet until the last moments of the movie. Which meant this film was way overdue a rewatch.
And what a rewatch it was. I'd nostalgically remembered this movie as being the pinnacle of sugary-sweet romance. Rewatching it as an adult felt wildly different: gone were the two indisputably adorable, 100 percent morally sound leads I remembered. They were replaced by a guy who has a, let's say, old-fashioned attitude towards women, and a woman who is pretty damn morally dubious with regards to her relationship to her fiancée, who she proceeds to string along for months while pursuing another man.
In short, I found I'd gone from completely doting on the two leads when watching it first time round as a kid to finding them the absolute worst watching again an adult. And they weren't the only ones — even adorable little Jonah, Sam's son, came off as a real jerk. Weirdly, the two characters I liked most on the rewatch were the ones I found putrid as a child: Sam and Annie's initial other halves. So here, without further ado, are the 40 things I noticed rewatching the Nora Ephron masterpiece as a fully grown woman.
1. Annie's Fiancee Walter Is A Monster
...because he has a lot of allergies and is called Walter. What? Literally, aside from these two characteristics, he's an absolute doll. He treats Annie with love and respect, gives her space when she needs it, and doesn't get paranoid that maybe she's fallen for another dude via his voice on the radio, even though he probably should. Poor Walter. I'm rooting for you.
2. Sam Baldwin's Boss Tells Him He Needs To Get A Grip On His Life Following Baldwin's Wife's Death
But he's chosen to wear this bow tie to work, so maybe he's the one who needs to take a long, hard look at himself.
3. Sam Is An Architect
4. Sam's Deceased Wife Is A Babe
And she launches the film's aesthetic theme of women-dressing-like-Princess-Diana, i.e. like young hotties dressing like they're about to go cut the ribbon at an opening of a mall.
5. The Characters Spend, Ooh, 90 Percent Of The Movie On A Landline
Which makes me feel better about my own overindulgence of smartphone time. Maybe pre-smartphone, everyone just had landline addictions instead.
6. You Can Tell It's Pre-Recession Because Sam Baldwin Has Two Phones In His Home For No Good Reason
Perfect for when your kid calls a lonely hearts radio hotline, and you need to set the record straight to the whole of Chicago.
7. You Can Tell It's Pre-Recession Because Annie's Childhood Bedroom Looks like This
It's a magical grotto of decor enchantment: want.
8. Her Mom Gives Her All The Feels By Talking About How She Met Annie's Father
And how it was fated and sexy and magical and she just knew. You have to understand this: she just knew.
9. Annie Does Not "Just Know," Which Might Be Why A Radio Show About A Guy Who Just Lost His Wife Makes Her Weep At The Wheel
Driving and crying on Christmas eve. Given all that traffic, sounds risky.
10. Luckily Annie Has A Best Friend, Becky, And She Is My Everything
She's played by Rosie O'Donnell, so obviously. Watch Becky carefully. Her face will be doing what your face is doing most of the time when rewatching this.
11. Like When Annie Tries To Pretend The Relationship She's Only Half-Into Is Ah-May-Zing
"Oh, please, I’m madly in love with Walter. He did the funniest, craziest thing the other night. What was it? Oh, we were in hysterics. Oh, what was it? Hmm.” Cue resting b*tch face. We don't believe you either, Annie Reed.
12. For New Year's Eve, Annie Reed Goes To An Elderly Person's Home Event
I don't understand. None of it makes sense. Why is Annie at a black tie gala with balding men and balloons for NYE?
13. They Talk About Going For Dim-Sum In New York And Walter's Like "But Does It Have Wheat In It?"
The crushing realization that your future husband's multiple allergies are going to put a serious cramp in your dim-sum habit.
14. It's New Year's Eve And Sam's Chilling On His Couch And Then His Dead Wife Appears
And Sam's like, "Nope. I definitely, definitely don't need therapy about my dead wife."
15. But Things Are Looking Up, Because Jonah's Radio Appearance Has Meant His Dad Has The Pre-Smartphone Equivalent Of A Totally Full Tinder Inbox
So many American women swiping right pre-swiping right via penning long, heartfelt letters.
16. So Sam Tries To Talk To His Son About How Dating Works
“It doesn’t work like that anymore. They ask you,” says Tom Hanks' son after his dad tries to give him a brief overview of what dating's like. “I’ve noticed,” Tom Hanks intones mournfully. Damn women's liberation movement.
17. Pre The Rise Of The Cool Girl, Rom-Com Heroines Could Have Pink Kitchens
Annie Reed, you're a maniac, but I can't resist your sugar-mice colored walls.
18. Annie Reed's Brother Looks So Familiar
Probably because he's Dr. Niles Crane from Frasier, which makes it extra lazy that he's been cast as a psychiatrist here, too. Still, as with so many of the minor characters in this movie, he's pure gold. “What we think of as fate is just two neuroses knowing they’re a perfect match” is his deliciously prosaic take on falling in love.
19. "I Don't Think I Could Let A Woman Pay For Dinner!"
...is the phrase Tom Hanks eye-rolls his way through. This is the first time we realize that Sam may not be a dreamy Cary Grant-esque lead.
20. "Tirimisiu?" "What's Tirimisiu?" "You'll See!"
I mean, there's a chance this is '90s slang for some sort of obscure sex act. But I think this might genuinely be urbane young architect Sam Baldwin having never heard of tirimisiu, which begs the question: Do marriages function like being shut up in a cave for several years? This might explain why Baldwin appears to have no knowledge of how anything — from dating to feminism to desserts — functions.
21. "What Are Women Looking For Now?" "Pecs And A Cute Butt."
So then Sam Baldwin asks his friend to check out his butt. His friend obliges: it's OK, he guesses.
22. Sam's Definitely A Loser In Love Because Even His Son, Jonah, Has A Cool New Girlfriend
She's amazing. She looks like a tiny child Cindy Crawford, and she shoots off sassy acronyms at every opportunity. "H and G." "H and G?" "Hi and goodbye."
23. Nobody Can Resist The Power Of A Romance Film
Even cool best friend Becky gets teary-eyed when watching the Cary Grant classic An Affair To Remember, which will inspire so much of this movie.
24. This Cannot Be How Computers Functioned In 1993
But, improbably, it is.
25. Despite Samuel Baldwin Not Being That Weird Of A Name, There Are Only Four Samuel Baldwins In The Computer
All of whom are either the best of men (world record holders) or the worst of men (criminals). Oh, aside from average-Joe architect Samuel Baldwin. Handy how that worked out.
26. Sam Decides To Go On A Date, Which Means An Appearance From The Best Possible Minor Character Clarise
Clarise is an unenthusiastic but competent babysitter and her outfits are all FIRE.
27. This Is Sam's Date, Victoria, And She's A Monster
Because she has a shrill laugh and sometimes she pays him too many compliments. Brrr. What a hag.
28. Jonah Hates Victoria So He Stops Them From Smooching Via Screaming
This is one of the few points in the film where I feel a little sorry for Sam Baldwin. The guy hasn't gotten laid in almost two years. A little rebound sex might not be the worst thing in the world.
29. Annie Goes To Seattle To Stalk Sam And This Woman's Face Says What We're All Thinking
Lady, get a grip.
30. She Prepares For The Occasion By Dressing Like Gandalf
Because nothing creates love magic like a large shapeless cloak.
31. She's Just About To Go Say Hi When She Sees Him Hugging A Woman
She does not stop to think: could it be a platonic friend? Could it be a relative? Because, rom-com.
32. She Almost Gets Knocked Over By A Lorry And Then Finally Sam Sees Her
Then there's a brief moment where their eyeballs make love.
33. This Film Is Way Too Comfortable With The Use of The Word "Ho"
Any woman who is roundly disliked is referred to as a "ho." First, we get Jonah, telling the radio love doctor about Victoria: “She’s a ho, my dad’s been captured by a ho, what am I supposed to do?” But, you know, he's a child. Then, we get fully-grown woman Annie Reed telling Becky, "She didn't look like a ho," about the woman Sam was hugging. Nope.
34. This Is The One Relationship We're All Rooting For Here
Because they both sport wonderfully bushy brows, because Jonah worships her, and because Jessica is a criminal mastermind who manages to book Jonah onto a plane to New York.
35. If You'd Forgotten What Date It Is, The Empire State Building Is There To Remind You
So obviously Annie looks out the window and is like... I can't do this.
36. Walter Reacts With An Amount Of Chill That's Disproportionate To How Completely Bad It Is That She Accepted A Marriage Proposal Despite Being Only Half-Into Him
Walter is the ultimate in classy. He's just like, "Oh, you've been in love with a disembodied voice while stringing me along for months? Cool, fine, cool. Go get him, girl."
37. She's In A Taxi But There's Traffic
Because last scene of a rom-com. So she takes to the streets.
38. I Can't Tell You About The Last Five Minutes Because There's So Much Stress
Will they meet? Won't they? I can't teddy bear it.
39. But It's Important You Know This: We Do Not Get Any Liplocking Action
Instead, we get a pretty flaccid looking handhold.
40. But They Leave Together
So I guess we can safely assume there'll be some smooching later. Phew.
The major revelation I had when rewatching this film was one you rarely get with modern day movies: namely, zero desire to either date or hang out with either of the leads. Sure, they're easy on the eye and have a certain charm. But their gender politics are problematic AF: Sam thinks ladies with a shred of independence are shrews, Annie thinks stalking is A-OK. Nope. If I resided in the world of Sleepless In Seattle, I'd happily hang out with Walter and Victoria, the characters the movie spends 90 minutes trying to convince us are drips. And this is the truly unexpected aspect of the rewatch: who knew the minor love rivals would come across so well in this movie, decades later? Not me.
Images: Tristar Pictures (41)