How one Charleston businesswoman turned dating into a numbers game

Perhaps love was just a numbers game, after all. So I decided to game the system with a challenge I called “52 Pickup.”

At 35, I was single and frankly sick of it. For nearly two decades, I had doggedly tried all the things everyone tells you to do to find someone: smiling at strangers over loquats at the farmers market, volunteering for sea turtle patrols on Sullivan’s, cultivating my inner artist with classes at Redux, joining Ravenel Bridge-running groups, being myself, being myself but better, not worrying about it, worrying about it, and “putting myself out there.” None of it worked. After focusing on myself, getting an education, building an in-demand interior design business, buying a home, and creating a fulfilling life, I thought I was okay with being chronically single, until suddenly I wasn’t.

As a woman of action, I needed a plan—a structured strategy with measurable results. If the approach involved a spreadsheet, all the better. The solution had to be bold, audacious, and inspiring—all the things I wanted my future life in love to be. Since waiting on quality partners to come to me hadn’t garnered any real results, I shifted my attention to quantity instead. Perhaps love was just a numbers game, after all. So I decided to game the system with a challenge I called “52 Pickup.”

The premise was simple: go on 52 dates in 52 weeks. As this amounted to roughly 10 times the total number of dates I had been on in my life, it was abundantly clear to me that “simple” wasn’t necessarily going to be “easy.” In order to have a chance in hell of meeting this arbitrary, self-imposed goal, I concocted a set of rules to live by for the year:

Rule #1: Actively date online

Since the average American male spends 1,169 minutes on his cell phone a week, I figured I would likely meet my guy on an app. So I immediately created profiles on all the major dating sites to maximize my exposure. While the initial flurry of interest seemed promising, it wasn’t enough for me to coast on beginner’s luck. I forced myself to swipe, like, click, and kissy-face emoji my way to exchanging direct messages. Anyone who expressed any level of interest received a response. If I got asked out on an actual date by someone who did not strike me as a potential serial killer, I said “yes,” put on a dress and a smile, and off I went—no exceptions.

Rule #2: Publicize

After years of well-intentioned friends and family members asking why I was still single—only to tell me everything I was doing wrong—I turned the tables and put those busybody, backseat drivers to work. Any time someone asked how I’d been or what I was up to, I told them I was dating and asked if they knew anyone I should meet. It took no time whatsoever to have representatives combing the tri-county area for someone, anyone, who wanted to hang out with me—if only to make me shut up about it already.

Rule #3: Be available

At the risk of sounding totally obvious, it’s much easier to be recognized by potential partners as single when you are, in fact, single. I made it a weekly requirement to spend an hour by myself enjoying the scene at a fabulous restaurant or bar, like Malagón or Graft. Distracting myself with my cell phone was off limits—the whole point was to be present and approachable. Once I let my friendly neighborhood bartenders in on the plan, the entire process turned into a damn good time.

The year passed in a pricey, cocktail-fueled blur. Some weeks I was up, with multiple dates and promising candidates. Some weeks I was down, with zero notifications on my dating profiles and nothing to show for my investment of time and lip gloss. I was occasionally stood up, regularly ghosted, and quite often propositioned in a very impolite manner—to the dude who told me I needed to “earn” my pizza, one slice at a time, you can hold the sausage, thanks! The big payoff was realizing that it was totally fine to not take any of it quite so personally.

While rejection in dating is the most personal form of rejection there is, my formula removed the pain. Since the goal was not necessarily to find my happily-ever-after, but rather to go on 52 dates, any one date was worth less than two percent of my success rate. After reviewing the math, I gained some serious perspective on the relative importance of one random stranger who may or may not want to sip a latte across from me at Harbinger for 20 minutes.

I built up quite a tolerance for rejection through my amateur version of exposure therapy. I also overcame a crippling fear of causing other people pain by learning to gently speak the truth when I couldn’t reciprocate romantic feelings. As my friends were complaining about the awkwardness of dating and worrying over whether yet another a shirtless dude holding a dead fish in his profile pic would call, I found myself removed from all that and pleasantly surprised by how much I was enjoying this grand experiment.

Spending time with the real people behind the dating profiles—many of whom I would have discounted as poor matches—was humbling. Absolutely everyone I had the pleasure of meeting had something interesting to offer, and it amazed me how willing people were to show up and try for love, over and over again.

As for the final results: did I succeed in 52 Pickup? You bet. In fact, I overachieved, with a total of 54 dates that year. Did I find a connection with someone incredible? Heck yes, more than once. Did it last? Not so far, but not everything beautiful does. The true win is that those relationships changed my story. Now when I find myself single, I know that I’m single for the moment, and not forever. If you want to learn more, you can find me sitting alone at the bar in The Dewberry, thoroughly enjoying myself.