The last of my still-single law school girlfriends showed up for dinner this past Friday with a 1.5-carat engagement ring. Meanwhile, I’m nursing a broken heart from my most recent attempt at a relationship. I’ll also admit to re-initiating contact with an ex from my third year of law school—the former Army Ranger best remembered for his unusual enthusiasm for his Breville juicer, premature ejaculation issues and borderline antisocial personality disorder.
I spent my last five years in Chicago attempting to forge lasting (i.e.: ultimately marital) relationships with friends of friends, and I’m still totally alone. My friends have run out of single guys to introduce me to. There’s even a running joke about the fact that I’ve dated THREE childhood friends of one of my law school classmates.
And don’t get me started on meeting a potential husband in a bar. Bars in Chicago are populated by three types: (i) snotty, preppy North Shore guys that I would rather pick a fight with than attempt to flirt; (ii) guys from the Western suburbs who all work at the Board of Trade and are not interested in committed relationships; and (iii) college kids.
That left me with few options other than the depraved world of internet dating, right? I’d previously ruled it out as too sad or desperate. I forbid myself from Match.com on grounds that the stalker-ish ex-wife of a partner I work for (who is convinced that a mythical affair involving yours truly ended her marriage) uses the site, and I could only imagine the online smear campaign if she saw my profile. And eHarmony is out of the question—not just because of the five million-part questionnaire, but because it seems too conservative. (It also has some connection with Dr. Phil, whom I despise.) Finally, there’s JDate, and—what else can I say—my college boyfriend upended my need to convert to Judaism when he dumped me after graduation.
All this kept my mind returning to those It’s Just Lunch in-flight magazine ads I resorted to reading on my last flight after I abandoned whatever dep transcripts I was supposed to be reviewing. Aside from the ridiculous name, I couldn’t help but find something a little bewitching about the concept.
The ad reiterated that the service is for “busy professionals.” Which means my excuse for resorting to such a service would presumably be my busy professional-ness—rather than the more obvious “I’m pathologically insecure!” or “I’m kind of a know-it-all!” or “I forget how to be sexy when I’m nervous!” Moreover, it seems that any man who would sign himself up for It’s Just Lunch MUST be incredibly desperate, and having that upper hand does wonders for my insecurities.
I scheduled the introductory meeting over the phone with a woman named Lizzie. (Never mind the fact it is completely ridiculous for an adult to call herself Lizzie.) I put a depressingly large amount of effort into my appearance as I readied for the in-person meeting. For starters, it wasn’t clear from Lizzie’s tone on the phone whether I was being invited to a sales pitch or an audition. As a lawyer, I’m conditioned to think in terms of tiers and rankings, and I was terrified of being banished to a lower, unspoken tier in the It’s Just Lunch dating pool if I showed up looking the least bit unpolished.
The building directory ever-so-discreetly listed my destination as “IJL.” Walking into the “happy” yellow-walled lobby and blaring Frank Sinatra initially sickened me, but luckily Lizzie and her Limited Express sexy-executive pantsuit whisked me into her private office before I had time to fixate. Her walls were adorned with framed, triumphant-looking human interest articles from a variety of second-rate publications. Each celebrating couples who had ended up in wedded bliss after their foray into IJL.
She described the pool of “hundreds” of eligible professionals. To illustrate, she read me the profile of a “real guy” from the dating pool: Brian—a six-foot-one, blue-eyed accountant who’s very athletic, loves live music, trying new things, and has traveled extensively in Europe. Lizzie continued to lay it on thick about how she’d only match me up with guys whose interview answers mirrored mine, and the process will be refined over time by my preferences. After dates, I would have to give “brutally honest feedback” to my rep, who would use the information to further refine subsequent matches.
I wouldn’t even have to share contact information or make reservations—my IJL rep will tell me when and where to go. Reservations are always made under the first name of both parties, and I’m only expected to share my contact information if I want to see the guy again. Oh, and I can go on as many or few dates per week as I desire. Hilariously, even though we’re all supposed to be “professionals,” Lizzie instructed me to allow the guy to pay if they insist.
Finally, notwithstanding the name, she let me in on the little secret: Most people choose to have their dates over after-work drinks. I guess “It’s Just a Drink at 7:30 at a Cheesy, Showy Restaurant in the Loop after Brushing Your Teeth and Putting Eyeliner on in the Office Bathroom” didn’t have the same pithy appeal.
It was as if Lizzie anticipated every question in my head and already had a neat, little answer waiting for me. How did I ever date before this ingenious service?
I pondered whether Lizzie’s manipulative skills matched those of Charles Manson’s, or whether I’m just particularly desperate—but by the time she casually slipped in that a full year of buffet-style blind dating would cost me $1,800 (non-refundable cash or check, of course), I was pretty much convinced that there was no other rational way for me to romantically function in Chicago.
Since what I’m really looking for is a high-earner with the financial wherewithal to slip a $20,000 ring onto my left hand after a whirlwind courtship, it seemed like a reasonable price… which brings us to the present. Me. Still alone. $1800 poorer. But with a glimmer of hope over the countless blue-eyed European travelers I’ll soon be joining for “just lunch.”
Read Law Firm 10’s follow-up to this post, ”It Just Sucks.”


