“There are no good men in Chicago.” Common sense aside, it’s a phrase I’ve heard almost every one of my single girlfriends say. Heck, I said it a few dozen times myself before I re-met the guy I’m currently seeing, four years after our first blind date (more on that later).

Most recently, I heard it from my newly single friend Debbie, 29, who came back to visit her hometown of Chicago while she mends her broken heart. “There are plenty of needles in the haystack,” I told her over poached eggs Saturday at Silver Cloud, where we were brunching with several friends. “You’ll find him when you’re not looking.” Trite? Sure. But I firmly believe you meet people in unlikely settings at unlikely times. Debbie wasn’t so easily convinced; she’s fresh out of a five-year relationship and at a crossroads, trying to decide whether to move back to Chicago or continue pursuing her career in New York.

We were still sitting there, dissecting men and decoding relationships, when Hot Guy walked by. “You can’t tell me you don’t think he’s good-looking,” I said, pointing discreetly as the man in question took a seat a couple of tables away. “OK; he’s hot,” Debbie said, revealing a tiny chink in her near-impenetrable cynicism.

We were finally getting somewhere.

After a few more cups of coffee, we paid the check and got ready to leave. Hot Guy, however, was still on the premises; I’d been eyeing him eye us throughout brunch. “Someone needs to find out if he’s single. You do it,” I said to one of The Husbands, who was getting a kick out of watching four grown women act like giddy 13-year-olds. “Ask him if he’s single; give him Debbie’s number if he says yes.” 

Despite Debbie’s mild protestations, The Husband approached Hot Guy. “I’m sorry to do this, but I’m with four girls who are gaga over you,” he said. (OK, so guys aren’t always the smoothest pickup artists—especially when they’re doing the job for someone else.) “Are you by any chance single?”

Turns out he was, and he came over to meet Debbie and the rest of us on the corner in front of the Cloud. Awkward introductions aside, he and Debbie hit it off right away. They ended up spending the evening getting to know each other, and they’ve already talked about rearranging travel schedules to spend more time together in the coming weeks.

Sometimes making the first move—or having a friend do it for you—can pay off, a lesson I learned recently myself. About four years ago, one of my brother’s friends set me up on a blind date. Despite a serious hang-up over blind dates (an “unnatural” way to meet someone, I thought), I was impressed when The Date suggested playing board games at Guthrie’s Tavern (1300 W. Addison St.), one of my favorite bars. We had a good time, but for whatever reason, I didn’t return his follow-up phone call—typical of me at the time. “I wasn’t that into you, either,” he says now (yeah, right). But about two months ago, after a girlfriend’s bachelorette party, I ended up at Stone Lotus, where I bumped into him again.

This time I made the first move. “What have you been up to?” I asked, taking his arm in the middle of the crowded club. We did a shot together at the bar, finished our drinks, and proceeded to RiNo—not exactly the most conducive spot for getting to know someone. But, hey, things happen at unexpected times in unexpected places. We’ve been dating ever since.