Kate Goldbeck: From The Rolodex to Raya

My debut novel, You, Again, is a romcom loosely inspired by When Harry Met Sally. In the course of writing the book, I’ve turned myself into a Nora Ephron scholar of sorts and I find her version of the 1989 dating scene fascinating.

There’s a scene in When Harry Met Sally that captures what I can only imagine was a completely accurate portrait of your typical “commiserate with my friends about how hard it is to find quality dates in New York City” brunch with friends. In it, Meg Ryan’s Sally is given some tough love by Marie (Carrie Fisher). After learning of Sally’s breakup with her long-term boyfriend, Marie reaches into her handbag and pulls out a full-size Rolodex.

Can you imagine relying on your best friend’s contact cards for your next date? Without social media, how did people track divorces, moves, engagements, and babies? (WHMS’s answer: word-of-mouth and dog-earing the card—but imagine the labor involved in keeping that data current!)

I’m assuming the women of 1989 Manhattan weren’t wandering the streets of the Upper West Side armed with giant Rolodexes, but it’s a reminder of how technology has made it possible for us to find literally anything or anyone with a scroll and a few taps—and how challenging it must have been to meet potential partners in pre-digital times.

Since we’ve offloaded Marie’s Rolodex onto The Algorithm, here’s how I think the characters of When Harry Met Sally would fare on modern dating apps.

Sally:

Since Sally just got out of a long-term relationship, she probably hasn’t been on the apps in years, except to listen to Marie swear that she is deleting Tinder once and for all. But once she decides to get back out there, Sally would do her research. She’s a journalist, after all, so she would probably read a few listicles with tips on creating a profile and the four types of photos you must include. Sally would carefully select a selfie that appears to be a candid (she set up the shot over a period of hours in her apartment), a full body photo (wearing her classic fall wardrobe), a snapshot at a wedding to prove she has friends, and one photo from a vacation to prove that she loves travel (even though she and Joe never did fly off to Greece at a moment’s notice).

Sally’s profile would be fairly standard, but she would really excel at swiping. She would be as picky about her potential dates as she is about cherry tomatoes at the salad (very). Have you heard this woman place an order? The bar is going to be high. And the slightest deviation from what she wants will earn a left swipe. If you get to the in-person meeting stage with Sally you’ve already won.

Harry:

Recently divorced, Harry would always be new to the dating app world, but would dive in without a second thought. His photos would certainly include at least one shot of him at a batting cage or in the stands at a sporting event.

Harry would swipe right on every woman on the app.

With his high confidence, he’d excel at the on-app banter, before inviting you out that night (he’s spontaneous!), sleeping with you, leaving at 2 a.m. after you’ve fallen asleep, and never texting you again.

Until, three months later, you receive a “u up?”

Marie:

She’s the ultimate pro at dating apps and is fast and fearless with the swipes. She’s also not scared off by things that would be dealbreakers for most people. Her weakness is not being able to identify red flags before she becomes attached, which leads her into quite a few toxic situationships.

She maintains a large roster, but at least half of them are lying about being married.

Jess:

Almost certainly has a photo with a fish in his profile. He only swipes right on women he considers “beautiful,” not just “pretty”. On the app, he’ll immediately monopolize the text conversation by mansplaining his personal literary heroes (who all happen to be misogynists). He asks if you can connect on LinkedIn. He’s obviously rescheduled the dinner date at the last minute several times. When he eventually does show up, Jess fails to ask you a single question about yourself.

You, Again by Kate Goldbeck is out on 14 September (Penguin, £9.99)