I’d been to bars, work functions, parties, premieres and good friends’ barbecues, and I still hadn’t found a guy I liked better than the saved shows on my TiVo list. So I decided to take a more proactive approach: Instead of leaving love to chance, I asked five different people (of varying degrees of closeness to me) to go through their personal rolodexes and set me up with a single man they thought I’d like. Some were dreams, some were duds, but all turned out to be, well, real experiences. Here’s what happened.

Date #1
The setter-upper: My high-school friend
The set-up: Her older brother, Brian*
How it went: We arranged by telephone to meet for a drink at a French bistro after work where Brian was dressed in a suit, pulled out the barstool for me, and ordered me a glass of white Burgundy. I soon found out the details of his fabulous, gazillion-dollar job at an international news outlet and that he knew more than I ever could about politics, literature, Balinese culture, scotch, Japanese brokerage houses—you know, your average dream Jeopardy! champion. He was also 10 years older than me, recently divorced and balancing visits with his two children at his house upstate with a job that requires 12-hour days on weekends. Brian was clearly an incredible catch, but it quickly became evident that our lives are different—really, really different. After we ordered a few appetizers, he took a call from one of his daughters who was crying over bedtime, plus one urgent call from work. As he stepped into the restaurant foyer to take each call, I checked up on the funny, childish things my girlfriends kept texting me from an outdoor garden where they were having cocktails. Brian finally surrendered to his life and apologized that he was going to have to leave early. His life was calling. And as we parted, it was unsaid that although we might be great dates for other people, we were probably not right for each other.
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Date #2
The setter-upper: My hairdresser
The set-up: One of his male clients, Gil*
How it went: After getting a cell-phone call from Gil asking if I wanted to meet for a drink, we picked a local bar a few blocks from my house famous for its draft beer selection. I was pleasantly surprised when I saw him: He wasn’t tall, but he was very good-looking, with a sweetly rugged face that reminded me of Scott Speedman from Felicity. We each arrived 15 minutes late, yet about 30 seconds apart. We chose the same Belgian white beer. And we discovered we shared the same inexplicable pull to the film Shattered Glass every single time it comes on cable, which is why we’d both seen it about 18 times. We were on such a roll chatting, he suggested we grab a bite. I was craving sushi. “Feel like sushi?” he asked. As we walked the 10 pretty, tree-lined blocks toward the restaurant, I was grinning from ear to ear, thinking about how badly I wanted to hug my stylist for his freakishly successful set-up. And then it all went to pot…literally. Three blocks from the restaurant, Gil pulled out a pipe filled with, how do I say this, munchie-inducing leaves and asked me if I want to smoke any of it before we got to the restaurant. I stammered and stuttered and nearly tripped on the sidewalk, I was so stunned. “Uhh…no… thanks, but no,” I said—though in retrospect, I wish I had called him on his actions. I guess I couldn’t decide which was more shocking: The fact that he was pulling out an illegal substance on a first date or the fact that he was pulling out an illegal substance on a public street, and I just stood there speechless. Gil took a puff himself, and the chatty connection we had earlier went up in smoke right along with it. During dinner, Gil barely said a word. He just ate, nodded and grinned like he was in another world. His world sure didn’t gel with mine, so we hugged goodnight (I saw him reach for his pipe again as we parted ways), and I started looking forward to seeing the guy behind curtain number three.

Date #3
The setter-upper: My female married friend
The set-up: Her husband’s friend Charles*
How it went: Ms. Married has been talking about this guy she’d wanted me to meet for ages, and since this is the month I’d made it my job to take some big chances, I agreed to meet him at an English pub. Charles was my age, and an attorney at a real-estate firm with dark hair, warm eyes, and a terrible cold. We discussed his work, my work, and then, for the next hour and 20 minutes, his obsession with The Grateful Dead. Not just The Grateful Dead, but the Jerry Garcia-less band The Dead, plus Grateful Dead cover bands, memorabilia and bootleg tapes he’s collected of The Grateful Dead, bands like Phish that kind of sound like the Grateful Dead, and… well, you get the idea. As much as I appreciated his passion for the music, I tend to strongly dislike things of or related to The Grateful Dead and cannot for the life of me figure out how this glaring difference got past Ms. Married. I changed the subject to our recent vacations (his involved a solo motorcycle trip to some concert in Utah), but by that point, his cold was getting so bad, the pile of wadded paper napkins in his lap was now about a foot high. “Yeah, we’re totally making out tonight!” he joked as he blew his pink, chafed nose for the 63rd time. We both knew the romantic connection was missing, and so we called it a night after two drinks so Charles could crawl into bed and feel better. How did I feel when the date was over? Grateful. Oh, and matchmakers take note: When I later asked Ms. Married about the Dead-head factor, she said, “Oh yeah, he mentioned something about liking them, but I figured it was a passing phase.” Not so much.

Date #4
The setter-upper: A former co-worker
The set-up: A screenwriter friend named Robert*
How it went: Though we had emailed about grabbing a coffee later in the week, I took a new tack when my sister had to cancel our plans to go to the theater. I called and offered Robert the ticket, figuring that, as a writer himself, he might appreciate it. He was practically giddy at the thought. We tracked each other down with cell phones like a pair of metal detectors outside the theater (after I grinned stupidly at another man I thought was him for a few awkward minutes). I was pleasantly surprised when I met him. Talk about handsome! Robert was a great dresser and a perfect “play” date. After leaving the theater, we spent a half hour probing the meaning behind the play’s final scene and decided that instead of stopping for a get-me-out-of-here-fast cocktail, we’d go for a steak dinner and bottle of red wine. Dinner was delicious, comfortable and fun, and the conversation was flowing like the wine. We were definitely hitting it off and discussed the possibility of a future date before we were even done with our entrées. Unfortunately, I had to skip dessert so I could get home to finish an article I was writing. So we kissed goodnight on the steps of a church in the glow of a streetlamp (I mean…could it have been more romantic?), he hailed me a cab, and we agreed to do it again sometime. Wow, a successful set-up. Go, work-friend! Robert and I texted a few times over the next few days—and two weeks later met up to play pool at a dive bar. A third date is looking likely.

Date #5
The setter-upper: A complete stranger
The set-up: An hour after striking up a conversation with a couple sitting next to me at the bar in my favorite local restaurant, they mentioned they were in town visiting the husband’s single male friend Tom*, who was at home, chilling out. They were outgoing, good-looking and fun, and the husband, Joe, mentioned he was always trying to find Tom a nice girl. Feeling bold, I suggested they set us up. They obliged and called Tom right away. How it went: It took Tom some convincing to get dressed and come out to meet us, but he was as much a sucker for “carpe diem” thinking as I was, and he arrived 45 minutes later. The one thing Joe had told me about Tom was that “he’s hilarious, absolutely hilarious.” He asked if I could handle hilarious. How could I not handle hilarious? Well, hilarious, as it turned out, comes in many forms, and Tom’s was a loud, shouting, disco-dance in a china shop form. The first example I witnessed was when Tom showed up. He was about 6’2” with a crazy head of curls and a goatee disguising his baby face; he was wearing a red bandana tied around his left thigh, and said he’s trying to get the city psyched for the Bon Jovi comeback concert in New Jersey. He sat next to me and ordered a shot of tequila along with his beer so he could “catch up” to us, and then proceeded to spin a few funny stories about his week as a salesperson for some sports-related company. They were right; Tom was hilarious, but in the two hours we spent together, he asked me about myself, oh, approximately two times and spent the rest of the time holding court. I couldn’t decide which criteria from Psych 101 disorders Tom was fulfilling (Pathological narcissism? Middle-child syndrome?), but I had plenty of time when I wasn’t speaking to run all kinds of possibilities through my head. We exchanged cards at the end of the evening, and Tom emailed me the next day with a funny email link. He’d be a fun guy to have on my acquaintance list if I ever needed to liven up a party, but the love connection wasn’t there.

But that was OK. I still had Robert, the guy behind door number four.

So what did I learn? That every person who set me up saw me as suitable for shockingly different guys. I can’t figure out if each set-up reflects the traits of my personality that come out most when I’m with each person (like watching crap cable movies too many times) or if it simply reflects what my friends want for me (like a house and a few step-kids in the ’burbs), but I was surprised to find out that the person who came the closest to matching me with my ideal guy was not actually my closest friend.

Still, asking for help with my love life brought my friends and I (oh, and some strangers and I) a little closer than we were before. I also met some interesting people and earned a few new badges from the war stories. And I even met one guy I want to go on a third date with—and that’s what taking crazy chances like this is all about.

*First names have been changed to protect the person’s privacy.

Amy Spencer writes for Glamour, Maxim, New York and Real Simple. For the men’s version of this story, read Make me a match?.