Let’s Reconsider Sleepless in Seattle From Walter’s Perspective

Sleepless in Seattle is a wonderful, fundamentally hopeful movie that contains many lovely elements, including Tom Hanks at his Tom Hanks-iest; Meg Ryan at the height of her rom-com powers; a soundtrack filled with sweet standards; the direction of Nora Ephron, who also co-wrote the screenplay and spikes its sentimentality with her trademark wry, observant humor; a baby Gaby Hoffmann using social-media-ready abbreviations (“MFEO” for “made for each other”) well before social media was invented; and Rita Wilson recounting the plot of An Affair to Remember as though an emotional dam inside of her has just burst. Sleepless in Seattle is great, and before you try to tell me it’s not as good as You’ve Got Mail, please hush, because you are wrong.

However, as we commemorate the movie’s 25th anniversary — Sleepless arrived in theaters on June 25, 1993, and went on to become one of the highest-grossing films of that year — it seems only fair to acknowledge the movie’s most troubling aspect and the character most deeply affected by it. That would be Walter, the guy who gets dumped in the middle of a Valentine’s Day dinner so his fiancée (Ryan) can run off and test her chemistry with some dude she doesn’t know (Hanks) on top of the Empire State Building. And somehow, Walter is totally fine with all of this.

Sleepless in Seattle establishes fairly quickly that a normally practical Annie is capable of falling in love with Tom Hanks based solely on the sound of his voice — millennials who had a crush on Woody in Toy Story, I am sure you can relate — and that she has been brainwashed by a lifetime of watching classic romantic movies, so much so that she believes anything less than an epic cinematic romance may be a compromise.

Even though the film strongly suggests that such behavior is delusional — “You don’t want to be in love. You want to be in love in a movie,” Annie’s best friend Becky (Rosie O’Donnell) rightly notes — Sleepless in Seattle ultimately proves that Annie is right. It is possible to find the kind of connection that only seems to exist on TCM, with just a bit of tenacity, a dash of stalking, an obsession with An Affair to Remember so severe that it may qualify as a mental illness, and the help of a stubborn kid who runs away from home solely to confirm that Annie from Baltimore is, indeed, his widower father’s destiny.

Oh, and also, no compulsion about totally screwing over Walter, the fiancé portrayed by Bill Pullman as the human embodiment of playing it safe. Walter may be the quintessential example of the nice, onscreen dull guy who gets dumped for someone more equipped to light a female protagonist’s fire. (For more examples of this trope, see Lorenzo Lamas in Grease, Danny Aiello in Moonstruck, Paul Rudd in Baz Luhrmann’s Romeo + Juliet, and James Marsden in The Notebook … and Superman Returns … and, also, Enchanted. Honestly, it’s amazing how much Marsden got rejected in the mid-2000s.)

Technically, Pullman got his post–Sleepless in Seattle revenge a couple of years later, when he charmed Sandra Bullock away from a far less interesting Peter Gallagher in While You Were Sleeping. But Walter, the character, never gets justice. So after more than two-and-a-half decades, it seems right to briefly consider Sleepless in Seattle from his point of view. Because if you think for one second that Walter was just a pushover with a severe case of allergies who was totally satisfied with his relationship with Annie, then you are just as delusional as Annie after injecting a fresh hit of Cary Grant directly into her veins.

When we first meet Walter in Sleepless of Seattle, he is about to be introduced to Annie’s family for the first time. Over Christmas Eve dinner, in front of the most uptight group of upwardly mobile white people outside of a Woody Allen film, Annie announces their engagement. Within seconds, Annie’s father is already insisting that they get married in the garden at their house and laying out the entire reception menu.

Walter is perfectly polite about all this, but make no mistake: He is already developing yet another allergy, to everyone in Annie’s immediate family. Do you honestly think Walter wants to be linked to these people for the rest of his life, especially Harold, Annie’s brother-in-law who is deathly afraid of bees? He does not. After they fail to get his reference to the Lou Gehrig line from Pride of the Yankees, he realizes he actively hates every single one of them. But he says nothing, because he loves Annie and because Walter is a nice person, which was underrated in 1993, but now, in the nonstop meanness that is 2018, may be the most appealing quality a man can possess. Poor Walter. He was kind before kindness became a rare and valued commodity.

Walter also goes out of his way to make thoughtful, but not disturbingly grand romantic gestures, like suggesting that he and Annie should meet in New York City on Valentine’s Day weekend, stay at the Plaza, and start their wedding registry together. Imagine having a man who wants to take you to the nicest hotel in Manhattan and also gets totally excited about shopping for china at Tiffany, then saying to yourself, “No, I really think a bereaved dude I heard once on a radio show is the one for me.”

Walter is far from perfect. He’s admittedly pretty basic. Also, for some reason, he has no idea what dim sum is. But to be fair, Tom Hanks’s Sam also has no clue what tiramisu is. Both of these guys are severely lacking in their exposure to even entry-level ethnic food. But Walter is actually there for Annie. Also, he’s more alluring than you might think. As I learned from the movie Singles, if you tousle his hair and say, “There, now you look vaguely rockin’,” Bill Pullman can suddenly become very sexy. Annie can never be bothered to tousle his hair.

There are some who would say that Walter isn’t really there for Annie, because if he were, he would have picked up on the fact that she’s extremely obsessed with a man who lives in a floating house in Seattle and taken immediate steps to put some excitement back into their love life. But I think Walter does pick up on Annie’s weird vibes, but has enough confidence in their relationship to give her some space. He senses that she’s been distracted “since Christmas,” as he says when they reunite in the movie’s third act, but senses that she’s “come back from wherever she was.” She already said yes to his marriage proposal, so he shouldn’t need to woo her at this stage in their relationship. If she has doubts, she should work through them and discuss them with him. But she doesn’t, not for a while. She asks Walter if he ever gets nervous about getting married, and he says, “No.” Because Walter is never rattled by anything.

By the way, have you ever noticed how we never see anything Walter does outside of the time he spends with Annie? I guess what I’m saying is that I’m pretty sure he’s a superhero and we simply aren’t privy to the part of his narrative where he and Spider-Man team up to fight crime in what actually was the most ambitious crossover event in history. (Why do you think he wants to go to New York so badly? Duh.)

Anyway: Annie finally admits she was feeling a little unsure about their relationship, but adds that she’s sorted through all of her feelings and is happy. The two are in such sync at this point in the movie that they simultaneously blurt out exactly how many place settings they need for the hideous china pattern that, miraculously, both of them instantly agree upon at Tiffany. There’s an old saying about romance and it goes like this: Get you a man who is willing to force your wedding guests to overspend on the same hideous shit you also think they should be forced to buy. Annie has that man. She does not appreciate him.

Before I get to the most outrageous part of Sleepless in Seattle, I should acknowledge the elephant in this movie’s room. Walter works as an associate publisher at the Baltimore Sun, where Annie works as a reporter. That doesn’t make him her boss — technically, they don’t even work in the same department — but it does mean they are colleagues and that he sits higher in the chain of command than she does. That might make some of Annie’s editorial cohorts think she’s getting preferential treatment, even when she isn’t. The movie never raises any of these issues — that would have taken it in a whole different direction — but I mention them because they do add some spice to a relationship that is seemingly bland, and also because, as someone more concerned about the newspaper’s money equation, it would not be unreasonable for Walter to wonder why his fiancée has to be sent to what she says is Chicago (actually: Seattle) to do research on a story.

Times were more flush for newspapers in the 1990s but even so, this seems like an extravagance, and a definite conflict of interest on the part of Becky, who also happens to be Annie’s editor and effectively signs off on travel expenses so Annie can decide whether she definitely wants to cheat on the man she’s about to marry, or just kinda sorta. My point is: If Walter were a different kind of guy, he could confront Becky about this. Or he could figure out how to dig around in their primitive, 1990s CMS and find out what story Annie is actually working on and where she is actually going. It’s the kind of thing Annie would do. But Walter doesn’t. Because he trusts the woman he wants to marry.

Which brings me to the worst part of Sleepless in Seattle, which the movie only shows us in part: the moment when Annie finally calls off her engagement and tells Walter that she’s been pining for Sam, who is again, I have to stress this, a man she still has not met and does not even know. At this point, Walter is not only planning to marry her, he has just had his mother’s beautiful ring resized for her at Tiffany and spent a ton on a bottle of Dom Pérignon in a very fancy restaurant. He has every right to go ballistic, pour the Champagne over Annie’s head, and start sobbing at the table.

Instead he says this: “I don’t want to be someone that you’re settling for. I don’t want to be someone that anyone settles for. Marriage is hard enough without bringing such low expectations into it, isn’t it?”

He is calm. He is rational. He is more mature than anyone should ever be expected to have to be.

“Walter,” Annie says. “I don’t deserve you.” It is the most accurate statement Annie makes in the entire movie.

Walter smiles, takes the compliment, then more or less gives her the green light to run over to the Empire State Building to get it on with her Joe Versus the Volcano co-star in a much more crowd-pleasing context.

He says he’s okay, but inside Walter has got to be livid and heartbroken. Annie may have fallen for a man who lost his wife, but she’s taken the promise of a wife away from Walter in the process and she doesn’t even realize it. She’s made Walter a pseudo-widower before he even had the chance to be wed.

At the same time, I have to think he’s also a little relieved. Over the past two months, Walter has found his fiancée in a broom closet in the middle of the night, hugging a boom box. He has sensed her backing away from him at the time when they should feel closer than ever. He has slowly begun to realize that he will have to marry her at her parents’ house while eating cold salmon, because her father insists for some reason that cold salmon is vital to any decent wedding. Walter hates cold salmon. He also hates the dowdy Holly Hobby nightgowns Annie wears to bed every night. Speaking of which, for all his sneezing, snoring, and use of dehumidifiers and tissues, not once did Annie ever express real concern about Walter’s allergies. “Hey, have you considered seeing an acupuncturist? Let me see if I can find a good one for you,” is a thing she could have said, for example. But she never did.

So even though Annie and Sleepless in Seattle treat Walter like complete garbage, don’t feel too sorry for the unluckiest man-man-man on the face-face-face of the earth-earth-earth. (Again, that’s the Lou Gehrig line. Jesus, how many times do Walter and I have to explain this?) He may have gotten dumped on Valentine’s Day in the middle of a fancy restaurant by a woman who decided he didn’t match up to her fantasies. But the truth of the matter is, by not marrying her, he dodged a real bullet.

Let’s Consider Sleepless in Seattle From Walter’s Viewpoint