It’s time to discover what the pros can do. I dial up In Good Company (360 N Michigan Ave, 312-499-9900, igc-chicago.com), a two-and-a-half-year-old dating service for gay and lesbian professionals. At a meeting in its downtown office, I fill out a questionnaire, and then Emily, the company president, asks about my family, career, personal interests and taste in men, a process that takes a little more than an hour. As long as you’re matchable (and I imagine you’d have to be a complete moron not to make the grade), out comes the contract—an agreement that covers one year or 12 matches, whichever comes first, and costs $1,100. Considering the hours so many guys spend trolling Gay.com, I start to understand the cost-benefit analysis.
What happens, I ask, when a client finds Mr. (or Ms.) Right after just the first or second introduction? “Then they’ve made a great investment,” Emily replies with a big smile. There is a little leeway—if she finds a good match for you early on and you’d rather not date around, you can freeze your membership for up to a year while you decide if you’ve found a keeper. A day or two after the meeting, Emily calls to tell me about my first introduction, giving me his first name, profession and a few of his interests. IGC then arranges a time for us to meet—Sunday brunch at Charlie’s Ale House in Andersonville, one of more than two dozen IGC “member restaurants.”
I’m the first to arrive; IGC times our brunch well, just before the noonish rush. My date joins soon afterward, and he’s kinda handsome—although that’s not really the first reaction I’d like to have when I meet my future husband. He’s also socially awkward, and not in a cute way: For instance, when the conversation turns to theater, he tells me about the time he attended a one-woman show written and performed by a “crippled midget,” and how he felt weird in an audience full of small people. I manage this rejoinder: “Well, I guess you gained a new perspective.”
We share a chuckle or two, mostly over the spotty service and soggy French toast. He nonetheless suggests we tip 20 percent, so at least he can be generous. As these sometimes-awkward “thanks but no thanks” partings go, this one was pretty painless.
Figuring online dating isn’t my forte, I decide to leave the matchmaking up to the experts. Élan (311 W Superior St, 312-649-5500, elanrelationships.com) is a professional service that provides busy worker-bee types with suitable candidates for the job of “soulmate.” For $3,500, Élan creates a six-month business plan for your love life. The staff sets you up with people from its database of successful singles who, like you, are looking for a committed relationship. But before going on your first date, you have to schedule an in-person interview with an Élan matchmaker to discuss your ideal mate, among other deeply personal topics.
Exposed-brick walls, hardwood floors and large windows make the Élan office feel more like the classy loft of my housing dreams than a place of business. As soon as I enter, a towering, immaculate blond walks up and introduces herself as Meg, my matchmaker.
As she seats me in an elegant armchair and makes sure I have enough water, I notice her perfect bone structure and wonder aloud if Élan’s dating clientele may be a little out of my league. Meg says there is no need to worry and for now we should focus on what I want in a date.
“Um, I want someone who is funny and attractive. God, that’s so generic,” I say, taking a long sip of water. “Sorry, I guess I should have a much more specific definition of what I want.” Meg spends an hour or so asking me open-ended questions like, “How important are looks to you?” As I sputter out spontaneous answers, I wonder if there are women scurrying around the city clutching checklists of what their perfect man is like, because I certainly don’t know who Mr. Right is yet. But Meg says the Élan team should have a date for me within two weeks.
A few days later I get an e-mail telling me to meet my date at 7pm sharp at Rockit Bar and Grill (the matchmaker picks where you eat but you split the dinner bill). As I walk into the restaurant and spy my date (whom I’ll call “Mike”), the first thing I think is, Shit, I shouldn’t have worn heels. Mike’s a handsome guy with the classic preppy look except for a few tattoos, but he’s clearly shorter than me—I’m about 6 feet in heels.
As we sit in our comfy booth, Mike loosens his tie and orders a Fat Tire. Our food arrives and without saying a word Mike sticks his fork into a grilled shrimp nestled in my salad. I like him.
Our conversation glides between politics, addictions to coffee shops and arguments about the best places to see live music. As we escape to a different bar, Mike looks up at me as I struggle to walk, and asks, “How tall are you without the heels?”
“I’m 5'9",” I say.
“Good, I’m an inch taller than you,” he says, and we both laugh.
Mike says he will call but doesn’t, so I resign myself to going on yet another blind date.