First Date, Last Nerve

A Trilogy of Almosts

Dating can be like walking through a maze—sometimes you stumble upon a gem, and other times you find yourself face-to-face with someone’s deeply misguided idea of what constitutes a “fun time.”

These are 100% real first dates I somehow survived.

1. The Accidental Date (ft. Gelato and Guilt)

He said it was a casual hangout—just two friends exploring North Beach (San Francisco’s Little Italy).

I wore something cute. He pulled up in a luxury car and opened with:

“Sorry I’m wearing this on a date.”

Date??

Apparently, he’d planned the whole day like a romantic scavenger hunt, with sites far enough apart to trap me in his passenger seat.

He bought me gelato, then wanted coffee, then casually dropped, “My wife and daughter love this area too.”

Excuse me—what?

He leaned in for a kiss. I pulled away.

By the time he insisted on visiting my house to “see my art,” I was already spiraling into an existential crisis.

He’s easily 20+ years older. Rich. Likely a millionaire. Definitely delusional.

2. Mr. 300 (And Still Counting)

He was tall, dapper, Hungarian. All swagger, slow smiles, and dangerously good cologne—looking like the cover of Men’s Health magazine.

He gave me a two-second X-ray scan the moment I walked in.

His mother had come from nothing. His childhood? Tragic. His vibe? Trouble.

I smelled a f*ckboi wrapped in an unclear backstory.

I asked, bluntly: “How many women have you slept with?”

He didn’t blink. “Around 300.”

Three. Hundred.

I still don’t know if he was bragging, bluffing, or just building a resume for the CDC.

Either way, I ghosted—because STDs and unresolved trauma are not my kinks.

I wasn’t going to be hookup number 301.

3. The Lost Therapist

He chased me down on a Wednesday.

Said he was lost. (He wasn’t.)

I pointed the way. He doubled back. (Why is he still here?)

He said he just wanted my number. (Desperate.)

I gave it. Because sometimes I’m nice.

We met at a dark bar-café. He talked for a full hour—about his trauma, his darkness, and how he hadn’t found his healing yet.

I said only five words:

“Diego, what do you do?”

He was a therapist, and he called it a date.

I called it unpaid labor.

It was a session. And I was the therapist.

Some men seek love.

Some seek therapy.

And some just want to see art with a side of moral ambiguity.

Either way, I’m charging emotional rent next time.