My First (and Last) Attempt at Playing Matchmaker:

The Grand Delusion

In Los Angeles, matchmaking feels almost inevitable. It’s everywhere—on reality TV, in overpriced apps where “algorithms” promise your soulmate, and even whispered across Shabbat dinner tables, as your aunt suddenly lights up and gasps, “You know who you’d be perfect for?” If there’s one thing Angelenos are better at than juice cleanses and networking mixers, it’s convincing themselves they have the magical ability to bring people together. Unfortunately, my 25-year-old self was no exception.

Here’s the thing: I’ve always been a sucker for a rom-com arc. Blame it on my upbringing. Growing up in Beverly Hills surrounded by Hollywood glitterati, I lived for those Nora Ephron moments—when a gentle nudge of fate sends two people hurtling into a meet-cute that shifts the course of their lives. I convinced myself it was my duty to create that magic for others. Spoiler alert: What happened next was less “When Harry Met Sally” and more “When Becca Met Humiliation.”

The Victims—I Mean, the Couple

It started innocently enough. My friend Natalie was (and still is) a legit stunner: all cheekbones and effortlessly cool vintage outfits that look curated but are somehow thrifted. She is also profoundly unlucky in love. She’d been ghosted, breadcrumbed, and once—even worse—forced to endure someone explaining that they “don’t believe in monogamy” while flirting with the waiter. I decided enough was enough.

Then came Ryan. Ryan was the kind of guy who quoted Tarantino movies in every conversation and wore scuffed Converse to weddings, but he had charm. He was also a family friend. Emphasis on “family,” meaning my own mother cheerily referred to him as the “Jewish Timothée Chalamet,” even though the only thing they had in common was floppy hair. Here’s a fun fact about mothers: they tend to inflate things.

Natalie needed someone steady, and Ryan needed someone to veto any future man-bun experiments. I thought I was the genius who’d make it happen.

The Big Plan

The setup was simple—or so I thought. I’d host a midsummer movie night at my apartment. You know, cozy and chic: string lights that subtly screamed, “I am an adult now,” cushions everywhere, Air One’s finest popcorn. I hand-selected the classic film Casablanca, because nothing says subtle manipulation like a black-and-white romance starring Humphrey Bogart.

Ryan would show up late (“He’s just sooo busy, guys”)—cue Natalie locking eyes with him from across the room. They’d bond over a shared love for foreign cinema and uncover layers of depth that even Freud couldn’t peel back. Obviously, I’d take full credit in my wedding speech one day.

Where It Went Horribly, Hilariously Wrong

I should’ve noticed the first red flag when Ryan called to ask, “Do I have to try at this thing?” Apparently, making him wear a semi-presentable shirt required negotiations that could’ve rivaled United Nations peace talks.

Then Natalie arrived—looking gorgeous, as always. She brought homemade cookies, a move so considerate it contrasted brutally with Ryan’s eventual entrance, which came 45 minutes late. Not only was he unapologetic, but he showed up holding tacos. For himself.

Strike one.

But the real pièce de résistance came when Ryan, dear clueless Ryan, opened his mouth. As Natalie laughed about a missed flight to Copenhagen, he leaned back, smirked, and said, “I don’t really get why people are so into Denmark. It’s just, like, Ikea, right?”

Somewhere in the great beyond, Greta Gerwig sighed without knowing why.

Natalie, ever the class act, politely ignored him—which only made Ryan double down by listing the ways assembling a HEMNES bookshelf was the perfect metaphor for our “broken society.” (I wish I were exaggerating.)

Strike two.

The mood had already plummeted faster than my WiFi after watching too many Netflix trailers when Ryan pulled a bottle of tequila from his bag—yes, the same bag he used to carry tacos—and proceeded to launch into what he called his “philosophy keynote.”

Friendly note: If you need to warn people your “philosophy” involves tequila, there’s a strong chance it should remain unshared. Suffice it to say, Ryan’s heartfelt theories on reincarnation and numerology were not, in fact, Natalie’s love language.

Strike infinity.

The Aftermath: Lessons in Humility

Safe to say, Natalie didn’t text Ryan after that debacle—and Ryan, oblivious as ever, texted me to say, “She’s cool, but kinda intense.” Reader, I screamed into a pillow.

At first, I felt like a complete failure. My matchmaking fantasy had exploded in spectacular fashion, with me left holding the social equivalent of burnt popcorn. But as I dissected what went wrong, three big lessons emerged:

  1. People Are Not Puzzle Pieces
    I’d been so focused on Natalie and Ryan’s “compatibility” on paper that I ignored their actual personalities. Ryan felt like the right choice because he checked random, shallow boxes (Jewish Timothée Chalamet being one of them). Relationships aren’t about perfect resumes—they’re about nuanced connections.

  2. Don’t Push Your Agenda
    Hosting a vibe-filled, manipulative movie night? I’d planned every single detail, down to the cushions, to force them into liking each other. But here’s the uncomfortable truth: you can’t engineer chemistry. That initial spark is either there or it isn’t—and no amount of string lights will change that.

  3. Know When to Exit Stage Left
    There’s a reason the best rom-com meet-cutes happen without interference. Sometimes, the most meaningful connections happen organically without some amateur director stage-managing the scene. Natalie—smart, radiant, and capable of spotting a tequila-based “philosophy” monologue from a mile away—deserved better.

Final Thoughts: Leave Matchmaking to the Pros (or the Rom-Com Writers)

The truth is, matchmaking is a gamble. We can have the best intentions and the flashiest rom-com-style script, but people? They’re unpredictable. They’ll bring tacos to flirtatious movie nights and fumble quotes from Casablanca, and maybe that’s all part of the chaos that makes finding your person so exhilarating.

For every Ryan, there’s someone out there who’ll praise Natalie’s homemade cookies like they’re Michelin-star worthy. Until then, I’m staying far, far away from matchmaking plans—and doubling down on buying string lights for my own ambiance instead.

As Bogie might say, this was an adventure in “the wrong thing to do for the right reasons.” Even so, I’ll always have the popcorn.