Side Order: A Meg Ryan Valentine’s Day, Three Ways

27 items to channel your inner Sally, Annie, or Kathleen

It’s almost Valentine’s Day, and despite the fact that I think romantic love is mostly annoying and I hate the word “Galentine,” I love nearly everything else about the holiday. Gifts! Flowers! Candy! Telling everyone you love them! A pink/red combo! And above all else, rom-coms.

Like every other millennial, I’ve made loving the romantic comedy a pretty significant part of my personality. Most years, I spend Valentine’s Day on the sofa with a roster of my favorites: Notting Hill, My Best Friend’s Wedding, Keeping the Faith, and of course the Nora Ephron trifecta of When Harry Met Sally, Sleepless in Seattle, and You’ve Got Mail.

In September, queen of the rom-com

Erin Carlson

shared a piece on her Substack called “The Unsung Inventors of ‘Meg Ryan Fall’” where she writes about the times she interviewed the costume designers behind When Harry Met Sally and You’ve Got Mail while researching for her book, I’ll Have What She’s Having: How Nora Ephron’s Three Iconic Films Saved the Romantic Comedy. It’s a charming look into the origins of the season in which we all don our Harry-esque fisherman sweaters and Sally-adjacent tweed blazers, and I thought of it when I was starting to pull together my own little groupings of products inspired by each of Nora’s main characters. But in doing some poking around, I realized that despite the fact that Meg Ryan’s Sally Albright, Annie Reed, and Kathleen Kelly each have their own quirks and unique senses of style, they all have one thing in common: an ultra-feminine, very late-’80s/early ‘90s, painfully cottagecore-in-the-city bedroom.

When Harry Met Sally (1989)

Sleepless in Seattle (1993)

You’ve Got Mail (1998)

All three films feature pivotal scenes that take place in the bedroom. In When Harry Met Sally it’s when Harry spends the night and then completely freaks out, in Sleepless in Seattle it’s when Annie sneaks out of bed in the middle of the night to listen to Jonah on the radio from the broom closet, and in You’ve Got Mail it’s when Joe crashes Kathleen’s sick day to bring her flowers and confuse her to no end. All three bedrooms are comically similar, complete with floral bedding, big stripes, and a hodgepodge of accessories that look like they came from your grandma’s corner antique shop.

So, my quest to come up with outfits each of these characters might wear today took a turn, and instead I ended up building assortments of products that reflect my own Valentine’s night in. If Sally, Annie, or Kathleen were spending her own cozy evening at home, what is she wearing? What book is on her nightstand? What candle is burning? And, if I were to make some changes and redesign each of their shabby chic bedrooms, what might I gently suggest?

Below, a deep dive into each version of Meg Ryan we all know and love, complete with loungewear, bedding, and reading recommendations aplenty: