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Sofi Papamarko remembers the moment she decided to become a matchmaker.

It happened while watching a friend dance to a Tina Turner song at a birthday party last spring. "I realized that someone I knew would absolutely love her, and I connected them a few days later as an experiment," the 33-year-old Toronto resident recalls. "I wanted to see if my intuition was right."

It was. She drew up a business plan for Friend of a Friend Matchmaking the day after the couple's successful first date.

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Her goal: offering personalized, affordable matchmaking for people like, well, her – "artists, writers, musicians, students." While many matchmaking services run upward of thousands of dollars, $99 gets you six months and two matches from Papamarko's roster, which includes approximately 200 singles. Her approach is personal, and thus, miles away from the murky world of online dating. She meets and talks extensively with each person that signs up, and draws connections between potential matches.

I decide to try the service to get myself out of a sort of personal dry spell. I'm 32 and after several years of focusing on my high-pressure career, I've been left with a string of hookups with guys that, for one reason or another, just didn't stick. The Friend of a Friend approach appeals to me, both as a busy professional who doesn't always have time to manhunt, and as someone who is horrified by the needle-in-a-haystack vibe of looking for love on a dating site.

The first step is filling out a lengthy survey with questions like, "What is your worst habit?" As a chatty Gemini, I am comfortable talking about myself, so explaining what I'm all about is no problem. Where I do stumble is on the questions that ask what I'm looking for in a man, something, I realize, I haven't thought about in a long time. I send off the finished survey and set up the second part of the FOAF process – a one-on-one meeting with my yenta.

With her pin-up girl bangs and huge warm smile, Papamarko is a disarming presence. As she sips peppermint tea and I nurse a much-needed pint of beer, I find myself in tears telling her about two recent heartbreaks. The conversation isn't easy, with Papamarko grilling me about what went wrong and why, but it's enormously cathartic, and by the time we talk about what I'm looking for, it's a lot easier to answer that question. For the purposes of my deadline, Papamarko forwards me the names, ages and tweet-length mini bios of three bachelors within 48 hours of our meeting. She introduces me to each prospective suitor via e-mail by sending us a joint note, and we are left to take it from there. Suddenly I have three dates where there were none. Sweet.

The first date is the scariest, partly because I'm rusty at dating and partly because we decide to go bowling. Mike is a 39-year-old comedian and actor who is clearly comfortable in the spotlight. He outbowls me easily, and confesses that he has spent some time practising his form while performing on cruise ships. While this isn't a love connection, Mike is fun, easy to talk to and a gentleman. The experience leaves me encouraged, and much less nervous, for my two remaining dates.

The next one is a cocktail date at a bar that is probably too hip for me with a guy who, at first look, seems too cool for me as well. Corey is handsome, sharply dressed in a vest and tie, and quick-witted in the manner of Jimmy Fallon. We talk for five hours before grudgingly admitting that, seeing as it's Tuesday night, we should probably part ways. He texts me the next day, and we make plans to see each other again. Suddenly I'm dating, like a real dater!

My meet-up with bachelor No. 3 is another first: a daytime lunch on a workday. A 28-year-old advertiser and filmmaker, Cam is tall and affable, but he reminds me of my brother, and our outing has an immediate platonic vibe.

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Looking back on the three dates, I realize the experience has been not only painless, but actually fun. I enjoyed meeting new people – especially straight men, each of whom I had at least one thing in common with. Papamarko's involvement took a lot of anxiety out of the equation, which allowed me to concentrate on whether I was having a good time, possibly the most important thing to think about when you're starting something new.

That weekend, Corey and I go out again and have another five-hour conversation that feels like five minutes. A few days later, I reach out to Papamarko one more time and ask her what made her match me with each of the three men. Her explainers range from "you mentioned your crush on Louis CK" to "you both work in media." She's curious about my perceptions of the dates, and I kind of want to dish to her over martinis, but have to remind myself that she's not an actual pal, though after the experience, she feels like one. At the end of the day, this was a business transaction. But a solid investment, it's safe to say.

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