Something I'm Obsessed With: While You Were Sleeping
'Tis the season to revisit this questionable holiday movie from 1995.
I regret to inform you that in 2023, you can’t stream The Holiday anywhere for free.
I did debate paying a few bucks just so I could watch the Kate Winslet monologue that got me through the many breakups and “breaks” of my early 20s (“I understand feeling as small and as insignificant as humanly possible…”). And, while I don’t care for Jude Law (sorry), I’m in love with that house in the English countryside, which isn’t as old as it looks and was built just for the movie. It’s just a feel-good watch.
Thankfully, The Holiday isn’t the only Christmas movie I like to play on repeat. There’s Elf, Home Alone, and, of course, While You Were Sleeping, which might be my favorite of the bunch and is currently streaming on Disney+. Sandra Bullock rules my September through December season, and just like Practical Magic, While You Were Sleeping always brings me comfort — despite it making less and less sense as I get older.
I now know that in 2023, Sandra — or Lucy, in this case — would probably end up in People’s Human Interest section, complete with a headline like “Woman Tricks Family For Weeks Pretending to Be Hospitalized Son’s Fiancé.”
If you haven’t seen While You Were Sleeping in a bit, here’s a quick refresher: while working her job at a tollbooth, Lucy sees her crush, Peter (Peter Gallagher), fall onto the train tracks, so she jumps after him and ultimately saves his life. She’s never even spoken to this guy before, but a quick mix-up at the hospital has everyone believing that she’s his fiancé. Lucy does attempt to tell people that no, she’s not, but Peter’s whole family keeps hugging her and his grandma has a heart problem, so she ends up going along with it — for the whole holiday season.
What’s most concerning is that at the end of the movie, no one really asks Lucy for a full explanation. Not Saul the neighbor, who knew all along, not Peter’s parents, not Jack (Bill Pullman), the brother of her fake fiancé, who (spoiler alert?) becomes Lucy’s real fiancé at the end, despite only knowing her for a few weeks. At one point, Lucy gives a quick speech explaining how she got swept up in it all — she was so lonely after her father passed away and missed being part of a family. But it barely answered all the questions that I would certainly have in this situation. The family thinks it’s fine, though, because they all show up when Jack proposes to Lucy, which happens before the two fully tell each other “I love you” or even establish a real relationship (they’ve barely even kissed). Seems a little risky to me, but hey, I guess people were more trusting and less suspicious in 1995..?
It may sound like I hate While You Were Sleeping, but I really do think it’s great. You have to suspend disbelief if you want to enjoy rom-coms, and everyone is so charming in this movie, it always leaves me with that warm, fuzzy feeling. Here’s what else I’ve been obsessing about after rewatching, in no particular (but kinda particular) order:
Sandra’s hair. Every time I watch this movie, I think about getting bangs. She’s got a whole messy-but-not thing going on throughout the film, and I’m now debating reviving a few ‘90s hair accessories, particularly these clips and this hair stick thing.
The clothes. I’ve written a bunch of stories about Lucy’s sweaters (see here, here, and here) simply because they all look so cozy. The oversized gray one from the beginning of the movie, her cropped cardigan, a cable-knit design that she pairs with sweatpants (see top image) while taking down her tree — ugh, I love them all. She also wears a cute printed maxi skirt while celebrating Christmas and gets almost-married in a dress that features a rosette embellishment, both of which feel very on-trend for 2024.
Peter Gallagher. The man plays someone who is in a coma for most of the movie, yet he still gets third billing! To many millennials, he’ll always be Sandy Cohen, the dad from The OC. But he’s also the real-life dad to one of my favorite interviews, Kathryn Gallagher, a singer, actress, and Broadway star. I had to revise my article on her three times over the course of 2020 (the world, as you know, was chaos) and I (accidentally) spoke to her for hours each time I did — she’s that chill and fun. Now, I can never look at Peter without thinking about her. (Unfortunately, the article was deleted for “SEO health” reasons or whatever, but at least the shoot, which was also styled by me, lives on.)
Bill Pullman. Forever the drunk ghost dad from Casper, but also the dad of Lewis Pullman, who currently stars in Apple TV+’s Lessons in Chemistry (sorry, I love a nepo baby). I have yet to watch the show, but my own dad loves it (he’s a Brie Larson/Marvel fan) and Lewis is someone who, IMHO, looks just like their famous parent. Also, he used to date Andie MacDowell’s daughter, Rainey Qualley, which I don’t think we’ve talked about enough. We could have had a cute rom-com couple 2.0 here, but sadly, they broke up after two years together. (It’s also worth noting that Andie’s other daughter, Margaret, is an actress and married to T. Swift collaborator, Jack Antonoff. It always comes back to Taylor!)
Glynis Johns. They spent the whole movie worrying about this woman’s heart problems and hoping she doesn’t die, but the actress who plays grandma Elsie (who you might also recognize as the “Sister Suffragette” mom from Mary Poppins) is still alive today. Glynis Johns recently turned 100 years old, outliving the rest of Peter’s older relatives. Obviously, I was shocked to discover this, but also thrilled to find this video of her saying that her age is NBD.
“Life doesn’t always turn out the way you plan.” Such a simple quote that bookends this movie, but a perfect sentiment for the end of the year!
A Hallmark Movie in a Book:
At some point in the near future, I plan to sit down and finally finish the last few pages of this holiday-themed book. It’s one of the cheesiest things I’ve ever read (twin sisters temporarily swap places and both of them end up falling in love with guys while pretending to be each other). But, it’s an easy one and if you like Hallmark movies, you’ll enjoy it. I’m reading mine through the Libby app, but it’s also available on Amazon.
A Cool Thing You Didn’t Know You Needed:
I recently came across this sticky, purse-cleaning ball on Instagram and decided I need it. It’s meant to pick up all the crumbs, lint, and dust at the bottom of your bag/backpack, and when you’re ready to clean it, you just rinse it off and use it again. I even wrote about The Clean Ball for StyleCaster, noting that it’s the perfect last-minute stocking stuffer. (Wink, wink!)
An Old Wives Tale:
You can tell what side of social media I’m on right now because I cannot escape this baby manifestation trend. Apparently, if you wrap a baby gift or baby blanket and put it under your tree, you’ll have a baby by next Christmas. I’ve seen the videos so many times that I’ve been influenced to do it. I bought this one because it has stars and is a nod to our fake (but also kind of serious) baby name, Jupiter James.