42 Thoughts I Had While Rewatching ‘Sleepless in Seattle’

It’s been a very bad, no-good, horrible, rotten, 24 hours, and I don’t know about you, but when I’m seething over the loss of my constitutional right to reproductive freedom, I like to watch an old rom-com. (Okay, first I like to protest and donate to abortion funds, but when the anger and sadness have run their course, I need to watch something to cool off.) 

Luckily, Tom Hanks and Meg Ryan are always there for me. Below, find an unabridged guide to every thought I had while rewatching the eternal classic Sleepless in Seattle—released 29 years ago today.

1. Why the fuck did I think watching a movie where Tom Hanks explains to his small son that his mother has died would make me feel better?
2. The literal first scene of this movie is in a graveyard. I’m an idiot.
3. Hey, it’s Rita Wilson!
4. God, Tom was so young. So full of life. So much hair! Although I have to say, I prefer him as a zaddy.
5. Okay, Tom and his small son are moving from Chicago to Seattle. He’s adamant that he won’t start dating again. I wonder what will happen!
6. Hey, it’s the mom from Six Feet Under! I love this woman.
7. Meg Ryan is marrying a guy who seems to be allergic to everything. They met through a classic sandwich mix-up, as one does.
8. Small Son calls into a radio station asking the host to help him find his dad a new wife, and Meg Ryan overhears it/is charmed.
9. Oh, also, it’s Christmas!
10. Oh my God, I straight-up forgot Small Son and Tom live on a houseboat-type thing. I know they’re bereaved, but…iconic.
11. I wonder if this kid ever did anything else in Hollywood.
12. No credits since 2006. Hmm. I hope it’s because he earned enough from this movie to leave “the business” in his dust.
13. God, remember when everybody used to listen to call-in radio shows? No? I’m old.
14. Hey, it’s Rosie O’Donnell!
15. Apparently, 2,000 women called the station looking to be Small Son’s dad’s new wife. A little thirsty, ladies!
16. Oh noooooo, Tom’s dead wife visits him in a New Year’s Eve dream and he tells her, “I miss you so much it hurts.” I’m going to have to watch a much worse and less emotionally weighty rom-com after this.
17. Hey, it’s Rob Reiner!
18. All these thirsty women are now sending Tom fan mail, despite the fact that they don’t know what he looks like. Lex vibes!
19. Meg Ryan’s fiancé is wearing an all-red pajama suit that I can only describe as “toxic.” She’s clearly not thrilled about his snoring.
20. “What we think of as ‘fate’ is just two neuroses knowing they’re a perfect match.” Important and real statement.
21. Why does this guy Meg Ryan works with have a harp in his office?
22. All I want is for Rob Reiner to be my personal relationship consultant.
23. Oh my God, I did not know Gaby Hoffman was in this movie in her child-actor days.
24. Tom asks out Victoria, a decorator he works with, and is of course incredibly trembly and anxious and endearing about it.
25. I am so obsessed with Meg Ryan’s basket (literal white, braided basket!) of potato chips that I can’t even summarize what’s going on, because all I’m thinking about is how I need a chip basket.
26. Meg Ryan writes a letter asking “Sleepless in Seattle” to meet her at the top of the Empire State Building on Valentine’s Day.
27. It really is amazing that the two main love interests in this movie don’t meet until the end. Now that’s a fresh script!
28. God, the early-’90s proto-Google Meg Ryan is using to figure out who “Sleepless in Seattle” is is inexplicably depressing me.
29. Oh, she straight-up found Tom’s ex-wife’s obituary. That’s some next-level sleuthing.
30. LMAO, I forgot she runs a full background check.
31. Small Son loves Meg Ryan’s letter, but Tom is too busy wooing his decorator to pay attention.
32. Small Son gets Tom to agree to meet “Annie from Baltimore” at the Empire State Building on Valentine’s Day, and I have to say, the pre-“stranger danger” era was wild.
33. Small Son does not like the decorator, and in his defense, she has an annoying laugh.
34. This kid’s bedtime is 10 p.m.? Guilty widowed dad much?
35. Small Son completely cock-blocks his dad, and calls the decorator a “ho.” Yikes! But not within her earshot, thankfully.
36. Meg Ryan’s hair game is really on point in this movie.
37. I can’t even handle someone in the ’90s saying, “Don’t you hate flying?” They practically gave you your own king-size bed back then! Talk to me when you’ve flown Spirit in the COVID era!
38. I am begging Tom to stop confiding in Small Son about his personal life.
39. Aw, Tom sees Meg Ryan at the airport while he’s dropping off the decorator and is instantly in love with her, despite not actually talking to her.
40. Was there really an era when children could buy plane tickets and fly alone?
41. Apparently, because Small Son flies to New York to meet up with Meg Ryan. Tom follows him, obviously.
42. Meg Ryan ditches her boring, cursed-pajama-wearing fiancé and…she, Tom, and Small Son all meet on top of the Empire State Building! Tears! Love! Immediate family! The end.