All I wanted to do was sleep off a hard week at the office. But at eight in the morning, my husband dragged me out of bed to wait for our new cleaning lady to arrive. I didn’t want to be the one who had to wait, wary of that awkward, uncomfortable feeling of sitting around while somebody else cleaned my apartment. I had no idea exactly how uncomfortable it could get, though, until that day.

I sat on the couch and started up my laptop, hoping to get some work done while Alex went out and I waited for our new maid, who was running late. Two hours later, the buzzer rang.

When she walked in, I thought someone else’s guest had accidentally rung my apartment. Was the guy next door ordering in a hooker at ten-thirty on a Saturday morning? What a sleaze ball, I thought, until my door-guest clacked right on into my kitchen in spike-heeled stripper stilettos with winding black rhinestone-studded straps that wound around her calves and ended just below her knee. She had a striking face, high cheekbones and skin the color of perfectly brewed café au lait.

“Girl, where’s your cleanin’ supplies?” she asked.

“Hi,” I said, eyeing the shoes. “Do you need a place to change? You can use the bathroom.”

“Yes please,” She had a lovely deep voice, throaty and melancholic, like Billie Holliday.

As she came closer, I noticed something was different about her face, voice, and manner. Thick foundation. A telling lump in the throat. It hit me: this cleaning lady was a man. She was the type of transsexual women love to hate: tall and model-gorgeous, with a skinny waist and long legs. I thought Alex was playing a practical joke, that he was a willing conspirator in some hidden-camera show. Very Jerry Springer, I thought, as I braced myself for our transsexual housemaid to do some sort of strip show, like those “naked maid” postings I’d seen on Craigslist.

She strutted into the bathroom to change, but re-emerged a second later. She’d taken off her jacket, revealing a tight midriff top and tighter black shorts. She walked over to where I was sitting on the couch pretending to work, and turned around.

“Can you help me out?” she purred. “I tied the knot in my shirt too tight.” Sure enough, the skimpy top was double-knotted in the back to hold it together.

My first urge was to get up and run away, but I agreed, instead, to help her undress. “How did you manage this?” I asked, trying to be cool as she shoved her ass about an inch away from my face while I struggled with the knot.

Once I got the top loose and she was safely back in the bathroom changing, her stripper spikes sitting abandoned in the middle of my living room, I went downstairs to get the paper and caught my husband on his way in.

“Do you know you hired a transsexual?” I hissed. “She’s up there cleaning our apartment.”

“Oh, really?” he said and laughed. “So?”

So? This from the man who had been infuriated when I told him I’d once married my gay best friend to help him stay in the country? When had I become so judgmental?

I used to love going to drag shows with my gay ex-husband when we lived on the Lower East Side three years ago. We went to the Wigstock concert in Tompkins Square Park during the Howl festival specifically to see Lady Bunny host a drag revue, then danced until morning at Splash in Chelsea. I was even known to venture into the Cock on Avenue A, a hardcore gay bar. I rented a summer house in Cherry Grove on Fire Island, where a transsexual served Sunday Brunch. I never thought twice about it; I’ve always appreciated ambiguity, people who defy convention and don’t live by the status quo. Now, here I was, upset because there was a trannie in my kitchen.

So I was fascinated by unusual people and things until they crossed my threshold. I was willing to experience gender-bending culture outside my house, in bars and clubs, where it was fun and safe, like going to the zoo where the exotic creatures are contained in cages so they won’t be threatening.

“What’s her name?” Alex asked me. I realized I hadn’t even bothered to find out. I was worse than I knew.

We went back upstairs where he immediately introduced himself to the cleaning lady and I followed suit.

“I’m Christine,” she said.

I thought of Christine (George) Jorgensen, pioneer transsexual, and her subsequent celebrity. Our Christine carried herself as if she were famous; she had that diva strut even when vacuuming.

As she cleaned, listening to Salsa music, I got to wondering why I reacted to her the way I did. Was it because of the shirt incident, or that I found her sex-kitten demeanor intimidating?

Christine was a hard worker. After she finished with us, she had two more apartments lined up, she said, then went to work for a hairdresser.

“Hair is my specialty,” she said. “My dream is to open my own salon. I do makeup, too.” She swaggered confidently around the room, dusting, organizing, and snapping her fingers when she made a point.

I was ashamed of my initial distaste for Christine. Here was someone so different from any of the hip privileged people in my life, and I’d been prejudiced, something I didn’t know I had in me. When she was done with the apartment, the three of us sipped Coronas in the kitchen and talked for a while. Christine told us more about her hair-salon dreams and we explained the process of opening a bank account, since she said she wanted to finally get one.

We decided to hire Christine permanently. We copied her ID (I craned my neck to see it did say Christine, not Christopher) and gave her keys to the apartment. We still haven’t talked about the fact that she’s a transsexual. She hasn’t mentioned it, so neither have I. As one female-to-male said in Dr. Harry Benjamin’s The Transsexual Phenomenon: “I have always wanted to pursue the normal aspects of life without the stigma of being an invader of normal avenues.” She’s simply a woman, living her life—just like me.

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.