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Ah, Toronto, our funny valentine, a city where romance blooms like weeds in the cracks of the asphalt. Four of the city's writers remember ways in which the city wooed them, or they wooed in the city.

Tabatha Southey, columnist

When I first moved to Toronto, one of the first places I lived in was the Beverley Lodge, which was a run-down boarding house across from the Art Gallery of Ontario. One time, a drug dealer who lived on the floor below me stole about 15 of those big baskets of flowers covered in ribbons that are placed outside of newly opened businesses in Chinatown and piled them up high all around the outside of the door to my room. All the other girls on my floor, who were even more new to the city than me, and who didn't know about the Chinatown flower thing, thought that a millionaire was in love with me and they were really impressed.

I lived at Church and Gerrard and a man broke into my apartment. He crawled in off the fire escape through the kitchen window – I realized that later. But I was on my way to the bathroom in the middle of the night when I thought that I saw something move in the dark and so I went over and I poked at it. And I poked a spine. You know when you've poked a spine.

I turned on the light. He had his hand inside my boyfriend's backpack and there was a moment of mutual embarrassment because he was a criminal and I was naked and, interestingly enough, these things balanced each other out in terms of embarrassment. In Toronto.

I told him to leave and he did, but when the police came, they kept looking at my boyfriend, who had called them, and saying to him over and over, skeptically, as I told my story, “And so you were asleep?”

“That's right,” my boyfriend would say. “Asleep.”

“Asleep?” the policeman would say again, interrupting me, as in, not hiding in the bedroom?

“Asleep,” he'd say.

“So, you were sleeping?” they'd try again, as in, not sending your girlfriend out to deal with a criminal, alone?

And he'd say, “Yeah, asleep.” Because, really, he had been asleep. But he was embarrassed too. In Toronto.

Even though I didn't have much money, when, at the age of 16, I first came here, I used to take the subway just one stop because I believed, after years of dire warnings, that Toronto was much bigger than it is. I did this until, after a few weeks, I ran out of money entirely and I learned the real size of downtown. After that, sometimes, I'd just get on the subway and ride all the way around, back and forth, for an hour or so because I felt that the Toronto Transit Commission owed me and I wanted to get my money's worth.

When my best friend lived here, we always walked down in the railway lands on the first day it snowed, every year. We'd go to Aikenhead Hardware whenever either one of us moved into a new apartment, which seemed to me to be about every six months. She e-mails me from Wales, where she lives now, and she says that what she misses most about Toronto are the orderly shop windows. I still miss Aikenhead Hardware.

Russell Smith, novelist, columnist

I had told my girl I would be home by dawn. I was playing poker in an illegal place. There were no windows. I asked the owner of the place, “What time is dawn, do you know?” He said, without looking up from his cards, “Dawn is at 6:38.” My friend said, “No way. Do you really know that?” And the owner said very quietly, “Of course I don't know that. What do I look like, the Weather Channel?”

And I laughed, but I was scared of him.

In Little Italy and Little Portugal, you can find backyard grapevines so thick they make an almost-rainproof canopy over a square of concrete. On summer nights, if you eat under this tent, you light candles and they make a green glow overhead, a ceiling of furry verdure like a child's fantasy. Then you barbecue fish from Kensington Market and drink vinho verde and tell stories. If it rains, you go silent and listen to the pattering. The concrete smells wet and hot.

Waiting in a queue outside a mammoth nightclub, getting close to midnight, watching everybody get searched as we inch closer to the metal detector. A little Honda pulls up, black windows, neon tubing on the underside, a big chrome muffler. Five tiny kids pop out, two little guys in tight shirts and sunglasses, three girls in miniskirts.

They are none of them older than 22. They push to the front of the line, and murmur to the bouncer with the headset. I see the littlest guy peel off twenties from a roll. The bouncer pockets them. The kids are let through. It never would have occurred to me, 10 years older than these kids, to even attempt such a thing.

I don't smoke cigars, but I stop outside cigar stores in Yorkville to breathe in the smell.

When I first hung out at the Bar Italia, in its former location, next door to where it now is, one of its great attractions was that red wine was served in industrial-thickness tumblers. It made us feel as cool as the old men and their tiny cups of muddy espresso. Now, I realize I no longer find wine in tumblers romantic. I have had to admit that it tastes better out of a fine glass. This is a little sad.

Lisan Jutras, columnist

Last year, I stumbled across a hidden cache of houses in Chinatown, a neighbourhood I so loved that I couldn't have imagined there was any part of it I didn't know. But there they were, the houses of Glen Baillie Place, their façades flush to the alleyway, their backyards a tangle of drying laundry, etiolated trees, rusted patio furniture and other dank unidentifiable things. It was like finding out something momentous about the person you had been married to for years and years.

When I was in junior high, the Bloor-Yonge subway station at around 4 p.m. was a hive of loitering school kids. I particularly remember the hearing-impaired teenagers who used to flirt and carry on in front of the panel of closed-circuit televisions, gesturing passionately and dramatically. I wanted to be able to join in, but I could only watch enviously from the sidelines.

A good deal of my first relationship was conducted whilst double-riding a bicycle. It remains, to me, one of the great romantic icons of the city – a couple wobbling along the side of the road, giddy with nervous laughter and the strain of concentrating, knowing things could get out of control or dangerous at any second.

On a slushy and horrible winter's day, at rush hour, everyone heading home tired and crushed into each other's wet coats, the streetcar driver got on the intercom and said in a steady monotone, “Everyone please move to the very very very very very very very very very very very very very very very back.” We were all cracking up by the last “very.”

The streets of Toronto always provide. As a child, I found a handful of shattered glass from a car window, which I threw into my satchel and successfully (I thought) passed off as gems at grade school. When I was a teen, hungover friends of mine stumbling the streets found boxes of freshly baked pastries in the foyer of an unopened shop, which were quickly devoured, still warm, like fresh kill. After high school, literally in the middle of bemoaning the fact that I didn't know what to do with my life, I was stopped short by the contents of somebody's recycling bin: there, on top, was a copy of I Could Do Anything If Only I Knew What It Was. Later, when I had decided that What It Was was Becoming A Writer, I developed a pointed disgust (read: envy) with a certain author and, after spending half an hour mowing this person down in a heated phone call, I went outside and discovered, in my bicycle basket, a copy of a book by this selfsame reviled author. Autographed.

James Bridgman, musician, carpenter

I had persuaded a young woman to have dinner with me. We ate at a Hungarian restaurant not far from Honest Ed's. After dinner, and after I had made it clear I lived close by, she suggested we go for a walk. We strolled east along Bloor past Spadina, eventually cutting south into the University of Toronto. We sat on a bench. It was a cool spring night. She wore a turtleneck. She tasted like goulash. After kissing a number of places on her face, for variety, and also because her turtleneck prevented any neck work, I stuck my tongue in her ear. She screamed. A grey squirrel had hopped on to the bench beside us. She really hated squirrels.

We had finally started to play some gigs in town. One of them was the Jarvis House. The other side of the street from Second City, when Second City was in the old fire hall on Adelaide. One night, three bright, beautiful women started hanging around. All of them, or maybe one or two of them, were in the cast at Second City. They lived together in a house in Cabbagetown. They invited us over. We danced. We drank. It was announced that “no one can leave. No one can sleep until the morning Globe arrives, not until we see our reviews.”

Nobody was sure how the party at the Palais would go. I was skeptical the place even existed. A dance hall from the forties? What, are we playing a benefit for the March of Dimes? After decelerating off the Gardiner, one hundred K to zero in 15 feet, I found it. It was a time machine. Portraits of Basie, Ellington, Sinatra and Frankie Laine watched us set up. About 9 that night, I was lounging in the downstairs dressing room when the crowd arrived. A great rumbling blob. Halfway through the first set, Mr. O'Hara, the organizer, the party manager, found the keys to the deck overlooking the lake. And such a cool breeze it was.

I moved into the Annex in '76. I lived in a ground-floor apartment. The first afternoon, I noticed a woman working in the garden next door. Her back was to me. She was very shapely. That was Bessie Finkelstein. I was much too young for her. Soon I discovered the Bloor Super Save. A woman with an interesting smile was loitering nearby. We shared a short moment of eye contact. I returned home. Being a piano player at the time, I began to fumble pointlessly through double-note scales in my kitchen. Moments later, Bessie leaned in my kitchen window and started to yell: “My God! A woman is peeing at your door.” The woman from the Super Save ran out behind Bessie and exited the drive. I went to my door. A puddle awaited.