Pt. 2 Maybe Dating is Like Trying on Shoes?

The moment it hit me was one of those late afternoons that felt like a scene out of a slightly chaotic indie film.

Me and my friend—she of the leopard-print chaise lounge and zero-filter commentary—were halfway through a bottle of wine that we definitely judged by the label. Both of us single, both of us dangerously close to texting someone we shouldn’t, we finally said it:

"Maybe we need to start dating again."

We hadn’t been on a real date in a minute. Like, a real one—where you put on actual pants and pretend to be emotionally available. Somewhere between the third cigarette and the bottom of the bottle, we looked at each other and said, “Okay. Maybe it’s time we start dating again.”

And then, just as quickly: “But why are we even single?”

Cue dramatic sip.
Cue slow exhale.
Cue existential crisis.

Because honestly? We weren’t single for lack of trying. We'd dated. Swiped. Settled. Escaped. Recovered. And now we were back at square one, barefoot, buzzed, and burnt out.

“I wonder if we’re single because no one seems to fit,” I said.

And that’s when it clicked.

Dating Is Like Trying on Shoes!!

We’ve tried on every type of man:

1. The Heels – Tall, hot, painful.
The ones who look amazing, make your legs (and ego) feel great—but you’re crying in the Uber 15 minutes into the date because they brought up their ex again.

2. The Dad Sneakers – Supportive, safe, snooze.
He texts back on time, remembers your cat’s name, and wants to settle down. But your group chat is asleep at the screenshots. There’s no spark. Just solid orthotic arch support.

3. The Platforms – Trendy, risky, unstable.
Fun at first. Then suddenly you're face down in the parking lot, wondering how you got here and why he still follows his ex on Instagram.

4. The Flip-Flops – Lazy and loud.
No effort. No real structure. Makes noise every time they show up in your life, then disappears at the worst possible time. Not even cute.

5. The Almost Pair – Close, but ouch.
He’s got potential. It’s 80% there. But you're forcing it. You tell yourself you’ll “break him in.” Meanwhile, your soul (and sole) is blistered and bleeding.

Honestly, sitting there with my friend, the scent of chlorine, cigarettes, and overpriced tanning oil in the air—I realized that maybe being single isn’t about being unlovable. Maybe it’s about being unwilling to wear shoes that hurt.

And honestly? That’s the most grown woman thing I’ve ever realized.