One woman puts herself out there so all you singles can reap the benefits of her dating disasters.
By Dena Levitz

Dena Levitz (Photography by Jonathan Timmes)
Back in the Victorian Era a man couldn’t just saunter up to a pretty lady who got his heart racing. If he managed to score a proper introduction, the best he could do was hand her a card at a party to demonstrate that he wanted to escort the dame home. She’d sort through the cards, weigh her options and then dole out her own card to the eventual winner of her affections.
A few centuries later, I guess we’d call that happy hour.
It’s safe to say that the delicate dance of attraction is very much intact. But the strategies and means to get there are far more expansive. Matchmakers have picked up where Yenta in “Fiddler on the Roof” left off. There are not only online dating services for subsets like vegetarians and interracial romance lovers; there are self-appointed experts who will help singletons write their profiles on these sites with all the gusto of a Fortune 500 company drafting a killer mission statement.
Everyone seems to have or want a hand in the business of love. So, as an unattached young woman in the Washington region, it begged the question: How are they doing? To better understand the search for “The One,” I spent the summer on the prowl, trying out online and speed dating, and utilizing a professional wingman.
Online dating: Scrolling for Don Juans
With Match.com and eHarmony commercials dominating TV land, I knew any study of dating had to begin on my computer.
First, though, I had to confront my bias against online dating. Even though my friends insist it’s gone mainstream with decidedly “unpathetic” devotees, the voice in my head said otherwise. A brief stint on JDate—specifically a date with a short man who asked me to remove my heels so he could be more secure—soured me. But, after considerable soul searching, I resolved I had nothing to lose by trying Match.com.
In years past, Match was less focused on the actual matching and more of a forum for relationship-seekers to be among their own kind. Recently the site has tried to have a say in who pairs up instead of leaving clients to do the guesswork unsupervised. The best example of this is the daily matches, where I could say “yes” or “no” to a lineup of pre-selected men. Those that got the nod received a notification that I was thinking about them, and we could move on to something more natural like winking. The feeling created was that someone was on my side, rooting for my success, filtering through the thousands of options and picking the best based on my personal needs.
Quickly, I realized this was giving the Match gods a bit too much credit. By week two every guy said to be in my wheelhouse sounded exactly the same. I thought I’d lose it if I had to read another profile about a thrill-seeker who had traveled to 30 countries and could make me roll over in laughter (often despite the fact that his 20 profile pictures showed the type of intensity reserved for axe murderers). It was as if every man had been slipped a secret playbook to sound like the Northern Virginia James Bond. Picking out the truthful ones was tough stuff.
I also tried, in my profile, to keep my male wish list vague. The trap I didn’t want to fall into was creating a “Weird Science” prototype and then deducting points if men departed from the checklist and, say, flocked to Steven Segal films. My main criteria was that the man be childless and within 10 years of my age. Still, there were plenty of responses from 50- and 60-year-olds who claimed to “seem a lot younger” than the number on their driver’s license.
Perhaps the biggest challenge associated with online dating, though, was moving the process along. One of the main differences between eHarmony and Match is that eHarmony prevents singles from meeting too soon with rules on how many online interactions have to occur first. Match has no such rules, so I expected to go on as many dates as I could fit into my Outlook. What I found was a slew of men happy to email back and forth 15 times with no meeting in sight. I thought Match was a way to get introduced on the Web and then carry on the relationship in person. But some of these guys almost preferred doing the dating—not just the meeting—online.
Given all of these obstacles, the best situation I encountered was going out on two dates with a lawyer, coincidentally from my neighborhood, who, too, had a thing for “Seinfeld” references and IPAs. Conversation was easy, but, for better or worse, the spark was as dynamic as a flat Sprite.
The worst experience was going out with a third-generation Italian Don Juan. Apparently 45 minutes of banter about his government contracting work and European geography signaled that it was acceptable to run his hands far enough up my leg to comment that I had just shaved my legs and to hazard a guess about where I stopped the razor. When the check came, Don Juan flashed a cocky smile and asked if I wanted to “go halvsies.” I reluctantly paid my share, dumbfounded that enduring that level of sexual harassment merited buying my own margaritas. Outside the restaurant he went in for a goodbye kiss that I miraculously evaded using a karate block reminiscent of Mr. Miyagi’s teachings. All I could think was I was perfectly capable of meeting someone as slimy on my own.
Bottom line: Match works well for shy guys who have trouble approaching ladies. One gentleman who took me out on a happy hour date was so withdrawn the conversation became mine to steer. Two beers in, after full disclosures about family, birth places and life goals, he asked how to pronounce my name. “Why did you wait until an hour in?” I asked. “Oh, I didn’t realize an hour had passed,” he muttered back. “Time’s just flying by.” I tend to think this guy will get an education from online dating.
On the opposite end of the spectrum, for those willing to put the time in to aggressively fish, Match can expose you to the maximum number of potential mates. Personally, Match let me know that, whether through an email, wink or chat, I had interacted with hundreds of men. It’s the Web equivalent of regularly walking into a bar with a neon sign flashing “Available.” The plus is you don’t have to come face to face with the uninterested, but you also have to work the room like a baby-kissing politician.
Speed dating: Interviewing for love
Quantity and efficiency are certainly the names of the game when it comes to speed dating. Rather than electronically getting to know each other for days, weeks or a month, speed dating gives you minutes. At the two Arlington speed dating events I attended, the allotment was four per person—which can feel anywhere between a millisecond and an epic viewing of “The Ten Commandments.”
In the region, networking company Professionals in the City has the market cornered, with events most nights of the week. I learned that although there’s a revolving door of singles ready to get in on the action, there’s also a small crew of regulars incredibly active in the scene. This fact became all too clear when I met a male Photographer-About-Town speed dating. When he “friended” me on Facebook I learned that my two-years-younger sister was not only acquainted with him on social networks, they had gone out after meeting speed dating. A few weeks later, Photographer-About-Town sent me an email via Match.com, oblivious that we had crossed paths before. The man was everywhere!
Just like with online dating, speed dating participants varied greatly in intention. At an event for 25- to 35-year-olds, a man in a dark suit who’d turned 35 in the early ‘90s took copious notes on serious questions about what I bring to a relationship. Then a few men later, a teenage-looking Italian sat across from me. It didn’t take much digging to realize this was his last night in the United States. I didn’t understand it. If bedding American ladies was his objective, there were easier ways.
The Washington region’s reputation as a career-obsessed bastion was most pronounced at speed dating, where conversation tended to dwell on job paths. In these types of situations, I crack jokes and ask off-the-wall questions about super powers, rabbits, anything to veer away from sexy topics like 401Ks. Doing so resulted in one date with a self-professed computer nerd—we lost steam after 15 minutes of conversation—and email exchanges with a few more. The most memorable was Former Army, who came off as incredibly kind, perhaps too kind in his mind. Within a week he texted me that, even though he was a good guy, he could “lick it like you’ve never had it before.” When I didn’t reply instantly, he messaged back asking about my favorite flower. We never met up again.
Bottom line: The quickness with which I was able to evaluate a few dozen prospects is appealing to busy people. I may have not met my ideal match from the events I attended over the summer, but maybe if I regularly did speed dating, I would meet him. Then again, I might just run into or, worse, become the Photographer-About-Town.
Wingman: Hiring a flirting cheerleader
When these more conventional approaches didn’t do the trick, I stepped out of the box and tried a wingman.
TheProfessionalWingman.com bills itself as the real-life “Hitch” and allowed me to try out their services one evening. More than two years ago, Thomas Edwards managed to turn a knack for helping others meet members of the opposite sex into a business. Since then he’s worked with a few hundred single men and women in Boston and New York, doing everything from helping clients approach and flirt to more full-scale lifestyle consulting. The Washington region is his newest market.
Prior to my night out, Kyle McKinney, the area’s dating coach, met with me to do a rundown of my romantic resume, interviewing me about my past relationships and future goals for a mate. Then it was on to business.
Often, Kyle spends considerable time with clients getting to know them so that a natural friendship develops—or at least can be portrayed easily. If not, they might come up with a backstory to avoid having to say “This is my wingman” when out in the field. To help me, though, Kyle was more fixated on seeing me in action. At the last minute, Kyle offered up a few pointers for how to handle myself: Stand near a busy part of the bar, look friendly, smile and seem approachable. He also advised, “If you see someone you want to talk to, go ahead.”
Too bad there wasn’t. In fact the first bar ended up being a bust. Kyle observed from afar for a half-hour, as a middle-aged man continually came up to me asking about D.C. landmarks, and I made small talk with the bartender about scotch.
By the second bar, Kyle became more of a director, walking in before me to scope out the scene. He reported back that a brunette guy was sipping beer alone and would be my intended target. Trying to be a dutiful student, I sat down in my appointed spot and broke the ice by questioning why the swivel stools I was genuinely having trouble controlling were so hard to maneuver. The remark got a laugh, and we were soon able to chit chat about sports scandals, Hollywood marriages and the Metro. My wingman, in the distance, gave me the nod, and I assumed I was in. Perhaps I was until the man’s cute blond date walked in and pulled him over to a different corner of the bar. I had struck out. Or had I? Kyle assured me I had been terrific, adept at starting conversation and looking available. Yet I finished the night solo.
Bottom line: For women, a wingman acts as more of an observer and cheerleader, giving advice from a distance so as not to scare off suitors. Having a wingman help another man is an entirely different scenario. Kyle described several lines of conversation he’d use to help male clients and the active role he’d play in their pursuits. It seemed a viable option for a man needing a support system while on the prowl, yet lacking friends to get the job done.
So what did I get out of this experience, in sum? Funny stories. Extensive dating experience. A sense that luck really does play a role in love matches.
Erich Fromm in “The Art of Loving” makes the case that love is a complex skill demanding practice and concentration. Once you’re able to gain the insight to master it, though, love is the “only answer to the problem of human existence.” His writing, dating back 50 years, is as true as ever. For months I sought out a mate with the same dedication I devote to hitting the gym. I may not have found “the One,” but I feel ready to meet him, no matter how.
Let Me Break The Ice
Online dating takes pick-up lines to a whole new level. My time on Match was made interesting by the items in my profile that men seemed to focus on to get my attention. Here are a few stand-out correspondences from men on the site:
(in reference to a profile picture of myself with a beer in hand)
“Beeeeeeeeeer! I’ve search for you my whole life. good times. P.s. who’s the girl?”
“Hey did you feel that earthquake? Hope your ok up there. Hope to talk to ya some more, I’m messaging again because I figured it might help you know that I’m genuine and not just trying to have sex. I am off to bed.”
“Looking for a Princess
To spoil pamper and travel with. do you like Champagne ??”
(This followed a date that I had with a man where I learned he was between jobs and living at home with his parents.)
“Since I’m searching for a full-time job, if you could please keep your eyes and ears open for any opportunities I would really appreciate it! Or if you have any contacts who would be good to talk to that would be great too!”
“It’s great that you lump adventure into skydiving and trying salsa. Does this mean that you are not a fan of spicy food? Maybe you can relate, but being raised on matzoh and horseradish, it takes a lot of spice to get to me.”
“Hey there. The match folks seem to think we’d be a good match. yeah, probably completely random. But you do have a pretty cool profile
”
“Will you marry me goddess? I’ll move to DC, take your last name and make you smile with breakfast every morning.”
(Referencing the Oscar Wilde quote “Life is too important to be taken seriously” in my Match profile)
“Oscar Wilde is awesome….Just needed to tell you that.”
“Thought i’d send a shout out since i’m jewish and living life to the fullest in dc too. no one ever guesses my age – i am a nude model and you don’t have to worry about anything in that category
”
“So if you read 2 or 3 books at once, how does this work…you read a paragraph from each before going back to the previous?
”
“If you’re a goofball, tell me something you’ve done that will make me laugh.”
“Intellectually curious…so would my daily word search and weekly Where’s Waldo be considered ‘intellectually curious’?”
“How is mayor Gray doing these days?”
My dating experiment, by the numbers.
Altogether, I went on nearly 20 dates over the course of my research. But those are hardly the only relevant numbers. The Verve insisted that love is noise, and love is pain. I’d argue getting to love is pain, tediousness and perhaps the battlefield that Pat Benatar howled about. I found the process of searching for dates to be as time-consuming as any professional job yet without the paycheck or health insurance perks. To put it into raw numbers, getting to those dates took:
76 winks at me
11 men who asked me out but then bailed last minute or kept changing the time
5 men who made me a “favorite”
7 repeats—men who winked once, didn’t hear back and winked again
4 men who reached out to me post-speed dating events
1,783 men who viewed my profile on Match
203 men who came up during my daily matches that I gave a “yes” response to
3 men who said they were too good-looking to show their pictures to just anyone and would email them to me
(December 2011)
Tags: Dating, Dena Levitz, love, speed dating
Fabulous article. I’m sure most girls can relate to this one. Men are a strange breed so it’s good to try out quite a few.