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Big city love

When Toronto, my first love, lost interest, I headed to New York for passion and excitement. I found a sociopath looking for revenge sex and divorced men in pleated pants who adored having me as their wingman

From Thursday's Globe and Mail

This is the seventh of a series featuring Canadian writers' true tales of love.

I looked across the table at Toronto as he nervously fidgeted and cleared his throat. He was at a loss. Where'd the love go? I asked. Where were all those acting jobs he used to shower me with? He stared ahead blankly, not meeting my gaze. It was clear Toronto was losing interest, so before he could dump me I broke up with him first.

During that drought of 2003-2004 that many of us in showbiz remember all too well, I moved out of the one-bedroom apartment I could no longer afford and took the train 14 hours south to have an affair with another city. I'd dreamed of living in New York ever since The Kids from Fame and I figured, if I was going to wait tables and struggle in Toronto, I might as well wait tables and struggle in New York. I fell madly and passionately in love.

Love's first blush gave way to the reality that I needed a job.

I sort of wanted to be a waitress, but only one who could wear what she wanted, sit down most of the time, and drink during a shift. Unfortunately, such positions (and all good restaurant jobs in New York) are about as difficult to land as a plum acting role, and are generally reserved for the hot girl the sous chef is shagging.

So I answered an ad on Craigslist for a personal assistant. My future employer answered the door of his swellegant Park Avenue pad in Prada loafers. I had to contain a gasp as I stepped inside. Had I not been disturbingly smitten by his movie-star shoes and taste in art, I would have gathered that this guy was a creep.

I was to be in charge of his Internet dating. Yes, I was the one who would manage his various profiles on various sites and actually correspond with women on his behalf.

Apparently, he and his girlfriend had just broken up. Like the night before. He made it very clear that he was not to go one weekend without a date, so time was of the essence. He also very helpfully pointed out that he couldn't screw me because I was his assistant now, and that would be messy. Great.

He'd written these very blasé, non-specific profiles for himself, which made sense for a sociopath. The woman in me was disturbed. The writer in me was enthralled. So instead of walking out on the creep, I punched up his profiles, making him sound like a guy who actually wanted to meet someone, which he didn't. He wanted arm candy. He wanted revenge sex. And I was to help him get them.

I left this job after about a month. Fifteen dollars an hour wasn't cutting it, and Crazy looked like he was getting back together with the girlfriend anyway.

New York was proving to be a much more fickle lover than I'd hoped. The walls were going up. One minute he'd be there lighting fires under my ass, and then he'd be gone for days at a time. I fretted. Maybe I can't make it here. Maybe I can't make it anywhere. But then suddenly he'd be at my door at 3 in the morning as if nothing had happened. He'd snuggle into bed with me, proffering his divine afflatus, reminding me that I was a clever girl and that I wasn't in New York to effortlessly open bottles of pinot or cater to narcissists. I took him back. Of course I took him back. And, roused by the city's imagined belief in me and a desire to subsist by my wits rather than menial labour, I decided to invent myself as a dating coach.

I advertised on Craigslist, giving my service the catchy name Simudate. I charged $50 an hour, and my first session with new clients was almost always a simulated first date. Instructions were clear: They made dinner reservations. We met at the restaurant. They were given the option of being coached throughout the evening or to proceed as if truly on a first date, and then over dessert and double long espressos I'd dissect. The latter was the preferred tack.

As mercenary as these simudates may sound, they were but a small part of what I offered my clients. I helped newly divorced men in their 50s dive into Internet dating. I went to parties and bars with guys as their wingman. I did wardrobe overhauls, whispering in my clients' ears, “I want you to listen to me because I'm going to say something that will change your life forever: You will never wear pleats again.” I gave them my undivided attention and spoke the truth. And while the financial rewards were obvious, I was also thrilled to watch a client's confidence blossom.

I slowly began to realize that my relationship with New York, as intoxicating as it was, was pretty one-sided. I loved him desperately and he barely knew I existed. It's hard to have a relationship with someone when you feel invisible. The irony is not lost on me that I was making my living coaching people how to navigate their hearts in the same city where I was feeling utterly lost.

I'd first trolled the streets of Manhattan, vibrating with all the potential and electricity on offer. But the feeling shifted when I felt as if I'd scream if I was bumped into one more time. I was the extra pinball the player hoped would stay in the game but didn't go out of his way to track, bumping up alongside this body or that, yet never actually connecting with any of them. If you can make it there…

Suddenly I missed my old boyfriend, Toronto, and the bike lanes and the casting directors who knew who I was, and the produce stands on Roncesvalles. So one night I drank too much and I called. I wondered if all the things that drove me crazy would suddenly be endearing. Or maybe we just needed couples counselling. I wasn't sure, but I went back and we started talking things through. I took my stuff out of storage, got a waitress job and sat down and started writing a play.

Tracy Dawson's tragicomic play, Them & Us, premieres at Theatre Passe Muraille in Toronto in early 2009. Her websitcom, T&A, can be viewed at www.youtube.com/TandAtv. She divides her time between Toronto and Los Angeles.

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