Apartment hunting in New York City is like dating: in the search for the One, you’ll inevitably run into countless disasters along the way.

While my romantic relationship has been the model of stability for once, buying my first Manhattan apartment was like looking for love all over again. The idea of settling down gave me the chills, but after a year in LA, I had moved to New York City feeling ready to commit. It cost twice as much for a studio the size of my boss’ office than for a large house in the French countryside, but this is the Center of the Universe, and I was going to own a piece of it—a tiny one, but a piece nonetheless.

I scoured the New York Times listings with the studious intensity of someone looking for a mate on Match.com.

Bright, sunny, loftlike. 17 windows! This condo is a steal at $295,000!

My heart raced, but it turned out to be the waiting room of a doctor’s office.

The height of style—Junior one-bedroom in the West Village ($399,999) must see, won’t last

The building was entirely gutted, and if you’d opened the door to 6C, you would plummet straight through the floor, à la Duplex, into the apartment below. I remembered why I gave up on online dating: the descriptions in the ads very rarely aligned with the men I eventually met in restaurants and bars.

On my first date with broker Tom, we planned to meet at a luxury 24-hour doorman building in the heard of the posh Gramercy district. A junior one bedroom, which was, by definition “approximately 100 square feet smaller than a regular one bedroom” awaited me. The so-called luxury dwelling still looked like it had been outfitted in the 1970s. Tom knocked on the door, which was odd; owners aren’t typically home during showings. A small and slight old man opened it.

He smiled wide and toothlessly.

Tom stepped between us. “This is . . . Mr. Spatz,” he said, in the same way one would introduce an aunt they were ashamed of, or a wife to a beautiful woman they flirted with at a cocktail party.

“Nice to meet you,” he said, in a thick Polish accent.

Mr. Spatz, who had lived in that apartment since the late 60s, had aged to the point of moving to California to live with his son. The apartment had aged right alongside him.

“The floors, obviously, would have to be ripped out and replaced,” Tom whispered. “And the bathroom, well, it needs gutting. But for 500 square feet at $350,000 it’s a steal!”

“You’re right, it’s a steal,” I said. “From me.” Sarcasm was too typically an issue in my relationships.

Next, Tom steered me to the East Village to look at an 800-square-foot 1 bedroom on 11th and C.

One flight of stairs led me into an apartment overlooking a garden with a huge bedroom and an office. This is perfect, I thought. Then I heard the price: For $420,000, I could have bought a ranch or two in Montana, a palatial residence with a pool and six bedrooms in Dallas, sprawling acres in Oklahoma.

The following weekend, I came up with my own list of open houses. Of course, I got a call from Tom anyway.

“You have to see this apartment,” he said.

“But I’ve seen your apartments. They’re always the same.”

“I emailed you the address already. Be there at noon.”

My first stop was at a “European Cottage-Style Charmer.” Without my guy along, I felt more independent, capable. I got to the place on Sullivan right on time. Six floor walk-up. Okay, but it’s in SoHo. . . .

The dark-haired broker in the kitchen approached me.

“Hi, I’m Amanda, and this charming place is my exclusive.”

She walked me through two bedrooms with exposed brick, a large living space and quaint kitchen. It was beautiful, but I couldn’t shake the feeling that something was missing. Then it dawned on me.

“Where’s the bathroom?” I asked. Amanda pulled a curtain out of the way of the sink. “The shower is here,” she said. “The rest is . . . come with me.” She pulled a key off of a shelf, led me out of the apartment and down the hallway, and opened a padlock. A lonely toilet stood in what was otherwise a broom closet. She started talking about the low cost of renovation, but I was already halfway down the stairs. Amanda could keep her exclusive. Tom had won.

I emerged from the subway and walked to Fifteenth between Eighth and Ninth. I recounted the morning’s SoHo-rrible experience to Tom. He gave me an I-told-you-so smile and unlocked the entrance to a charming (in Manhattanspeak: “small”) one-bedroom flat, with shiny hardwood floors and new marble-top kitchen counters. It overlooked a quiet garden below. Rather than traffic, I heard birds. It was in the studio price range. The previous owner had already closed on a house, Tom explained, and wanted out. Fast.

The courtship phase neared its end with the board interview. “Err towards the side of being quiet instead of saying a lot,” advised Tom. “A board never turned anyone down for being too boring.” This is why it’s different from dating, I thought, as I sat in front of five people, trying to be as boring as possible. Two months later, keys were exchanged in a Midtown law office. You always fall in love when you least expect it, and I had finally tied the knot with Manhattan.