I don’t know what the deal is, but my single friends have been falling in love left and right. Even guys with ridiculous game have been sending rosy engagement notices. Is my heart too black for this to happen to me, or have I just been going about it the wrong way? This month, instead of blindly chasing dream girls, I asked other people to set me up on dream-girl blind dates. Will true love blossom? Only one way to find out. And here we go…

Date #1
The setter-upper: An ex-girlfriend
The set-up: Her college friend’s pal, Cindy
How it went: My ex introduced Cindy and me over email, and Cindy wrote that she recently ran a marathon, loves to ski, and makes jewelry for a living. Since I’m a runner, a snowboarder, and a creative type, she sounded promising, and we agreed to meet for dinner at a Cuban place. Now, it’s really annoying when you go on a date and the other person asks you nothing about yourself. This was not a problem with Cindy. Nope, she asked me so many questions, I felt as if I were on a job interview… or if the lighting had been harsher, a police interrogation room: Where are you from? What’s your family like? What’s your dream job? How do you feel about these plantains? I was flattered, at first, but the more we talked, the more I suspected this barrage of queries was her way of deflecting attention away from herself. That would explain her confession that she sometimes avoided people she knew on the street, ran her jewelry business under a pseudonym, and was big on “anonymity.” Then I tossed her a softball — “What are your favorite bands?” — and she refused to answer (!), instead asking for my picks. Sweet and inquisitive as Cindy was, I’m looking for an outgoing girl with strong opinions, and she wasn’t it. We hugged goodbye after dinner, and continued to be email friends, but nothing more.
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Date #2
The setter-upper: A former co-worker
The set-up: Her co-worker’s friend, Anastasia
How it went: An aspiring actress, Anastasia had been described as “a knockout,” and when we met up at a hip little Italian joint, that proved to be accurate: With long brown hair, wholesome Midwestern looks, and a toothpaste-commercial smile, she reminded me of Minka Kelly, the head cheerleader on Friday Night Lights. As we split a bottle of red wine, a tomato-and-cheese platter, and a prosciutto-and-arugula pizza, the conversation went smoothly. That was probably because it was mainly about her. We spent 87 percent of the dinner talking about her roommates, her family, her waitressing job, her acting dreams, her odd run-in with Gary Busey, etc. At 23, she was really just starting to figure her future out, and I indulged this talk, since I was once a struggling screenwriter in LA. And through no fault of Anastasia’s, this was what made me prematurely jaded about her—I had met so many starry-eyed wannabes out West, it was hard to get excited about another one. Plus, she was five years younger than me, seemed to have her guard up, and didn’t laugh nearly as hard at my account of spending six months working in a Ventura Boulevard tanning salon owned by a former American Gladiator as I would have liked. (C’mon, it’s a great story!) At the end of the night, we split an order of pistachio ice cream—a cool moment, not a romantic one. Earlier in life, I would have been totally taken with a girl like Anastasia, but these days, I just felt like I’d met her a hundred times before.

Date #3
The setter-upper: My high-school friend
The set-up: His friend’s former roommate, Samantha
How it went: I was initially hesitant to go on this date because of geography. While Samantha worked in my city, she commuted in from a nearby state, and I couldn’t help thinking of the old rule: Never date a girl you have to pay a toll to see. But by all accounts she was a catch, so I decided to make an exception. Five minutes before I reached the shabby-chic restaurant where we planned to meet, my cell phone rang. “I just got here,” Samantha said. “What’s your favorite drink?” When I arrived, a lovely, Grace Kelly-ish blonde sat at the bar with two ice-cold beers in front of her. And unlike a scene in some romantic comedy, she wasn’t waiting for some big, hunky dude walking up behind me—she was my date! It was enough to make a man reconsider the suburbs. Then we started talking. We seemed to have a lot in common—I enjoyed her stories about her newspaper job, hiking the Appalachian Trail, and trying to convince people her grandfather coined the Miller slogan “The Champagne of Beers”—and yet somehow it was a lot of work to keep the conversation going. Judging by the number of awkward silences (about one every fourth sip), it was clear we didn’t totally click. I realized that I wanted to like her because she was so attractive, a mistake I’d made many times before. After our meal and a few drinks, Samantha had to catch the bus home. Outside the restaurant, we shared a surprising smooch and talked of meeting up again, but in my heart I knew the distance — geographical and conversational — was too great for that to actually happen.

Date #4
The setter-upper: Erica, a friend of mine
The set-up: Her work friend, Jennifer
How it went: My friend Erica’s annual tree-trimming party was packed with single females, and she was quick to introduce me to Jennifer. Which is funny, because height-wise, I’m Tom Cruise and Jennifer is more Claudia Schiffer. With her three-inch heels, she approaches six-feet, which put me at about eye level with her chest. But as we shook hands (and drank), hung ornaments (and drank), and flirted (and drank), there was a real unspoken attraction. We had this connection where we told each other silly lies — she’s a magazine editor and said she just left Pottery Weekly for Kiln Monthly — and found it hilarious. I filched the only two beers in the fridge and accompanied her outside so she could smoke, and before either of us knew what was happening, we were smooching in the hallway. “Not at the tree-trimming party!” she laughed, pushing me back. I suggested we leave the party and get a drink together, and we got our coats. But as the buzz wore off on the cab ride to a bar near her place, I realized Jennifer’s kind of an awful kisser. She stuck her tongue way out and just kind of waved it around like a fencing sword, so that my lips could barely reach hers, and all I could do is dodge my tongue out of the way and try not to choke. Suffice it to say, this really killed the mood. I took her number, but even as I did so, I knew I’d never call a girl whose make-out style makes me think of Gene Simmons.

Date #5
The setter-upper: An old friend
The set-up: My friend’s mom’s boss’s daughter, Kristen
How it went: I wouldn’t normally go out with a friend’s mom’s boss’s daughter — too many degrees of separation — but at this point I’d try anything, so I agreed to meet Kristen at a hotel restaurant famous for its burgers. And having dated too many high-maintenance ladies, I immediately loved this slim blonde’s easygoing style. I’m 10 minutes late: “No worries,” she said. The only table available was a large round one, meaning we’d have to lean way across just to talk: “Fine with me.” When I asked how her day was, she said: “Kinda crappy. I forgot to order a car to take my boss to the airport, and he missed his flight and yelled at me.” Then, she took a sip of her wine, laughed and said, “This helps.” Being an avid carnivore, I was thrilled when she ordered a medium-rare half-pound burger with bleu cheese, mushrooms, and bacon. Later, in the midst of our animated debate about a well-known downtown burger joint — she loved it, I hated it — she accidentally tipped over her glass, spilling red wine all over. Kristen apologized profusely, grinned sheepishly at me and called the waitress over for napkins—and ordered a beer. There was something about the way she took her ups and downs in stride that I totally dug. We continued talking and joking, and when she ate every last bite of her burger, I was practically smitten. With work looming the next day, we had to call it a night, reluctantly. As we hugged goodbye, I realized I should’ve told her my tanning-salon story. Then again, when we meet up downtown so I can re-try that controversial burger, I’m sure I’ll have another chance.

So there you have it. I didn’t fall madly in love during my month of match-ups, but I met a lot of interesting people and came away with some pretty good tales. And considering my meager second-date percentage when meeting women on my own, the six degrees of separation set-up really ain’t half-bad. Perhaps my heart isn’t so black after all…

Steve Mazzucchi, a freelance writer based in New York City, has been published in Men’s Health, Women’s Health, and Maxim, among other places. For the women’s version of this story, read Set me up with a single guy!