30 Dates in 30 Days

These photos are not the real guys Greg, in the middle, dated. We're just trying to show he went out with lots of different ones and ... Oh, just read the story.

HIS NAME WAS Kevin, a date I’d landed via OKCupid. His profile: slightly witty, a horrendous speller, but cute, with a body for days. When I met him face-to-face, his looks didn’t disappoint. The home-cooked meal we had was a bonus, and a welcome nod to romance; most of my Internet dates started off with a quick cup of coffee, drinks, or some combination thereof. Seeing the labor he put into dinner, any judgments about his spelling faded. I began to think I’d hit the dating jackpot. 

It took but five minutes to flip that.

His overuse of the word “like” and his unfamiliarity with where Ohio is (one state over, mind you, and where I happen to be from) were caution flags. But what sent me packing was our discussion about my recent obsession, the HBO series Girls. As I sold the show’s merits, Kevin abruptly took up arms to my enthusiasm.

“Ugly people should not have their own shows,” he argued. He said he just couldn’t bring himself to celebrate the show’s ugliness. He didn’t mean the “ugly” struggles of Millennials, but the girls themselves. After dinner I made up an excuse about an early meeting the next day and left.

Maybe I should have stayed for dessert to hear him out. He did, after all, cook me a delicious meal. But though I was new to online dating, I had quickly figured out when to bail, one of many lessons gleaned from living single and dating in Philly. It wasn’t the last.

I MOVED HERE in 2011. For the past two years I’ve steered clear of dating. But seeing the ripe old age of 30 creeping ever closer, and tired from endless weekends in the bar scene, I was feeling ready for a boyfriend. The problem lies with the process: You date someone three, four times, then decide it’s not right, and a month has gone by. I wondered if there was a way to accelerate it all.

And so an idea was born: 30 dates in 30 days. The way I figured it, if you want something badly enough, why not commit and go balls to the wall? If you’re looking to get your body beach-ready, you work out like a fiend for three straight months; if you want to get an A on your poli-sci exam, you cram the night before. Could this theory be applied to finding a man? Was Diana Ross wrong? Could you, in fact, hurry love?

I created profiles on six dating websites. There were new rules: Grammar mistakes, not physicality, were cause for judgment. Witty one-liners, not confidence, netted a second look. But as well crafted as my words were, the truth of the matter was that my pictures were going to do most of the talking. I didn’t want to make waves with a barrage of shirtless photos, or images of my real life at home watching Rachel Maddow in my underwear. So I uploaded any gregarious photo I could find where tanks and shades were involved, snaps from dinner parties I’d been to in the last year to showcase my bow tie collection, and shots in public spaces where I was wearing a cardigan, latte in hand.

I landed a lot of dates online, and also through friends setting me up, meeting people at house parties, and (more than one) from “dating slut laps” at bars. The latter involved starting out with a breezy stroll around a bar’s environs, both cool and confident in my strut yet entirely attentive to any attention. If it was warranted and the attraction was mutual, I’d walk right up to the guy and attempt a flirty conversation with the aspiration of securing a date.

The first of my 30 dates was with a guy I met using this method. Contrary to my intentions, it didn’t exactly end innocently.

Jeff was a nice, attractive medical student who agreed to meet me for drinks the following Saturday. On the date, he disclosed his plans to move back to his home state of Texas—in two months. That pretty much sealed his fate right then and there. Long-distance wasn’t my thing, at least not for a guy I’d picked up on a slut lap at Woody’s. I could either get the check now and say goodbye, or call it what it was and make moves to get him into bed.

I got him into bed.

The next morning, I woke up next to him feeling a little slutty and with my stomach in knots. As I quickly shooed him out the door, I knew I wasn’t exactly off on the right foot for my 30-date marathon.

Guy #17 AGE: 26 HEIGHT: 5'10

PULLING MYSELF OUT of my shame spiral, I re-hit the dating scene: coffee with a West Philly artist (nice, but not cute), late-night drinks with two Penn students (not at once), and a historic walking tour with a recent Philly transplant (very cute, not at all nice). There were dinners with a 29-year-old server with an obnoxious baby seal-like laugh, a surprisingly loud but incredibly boring 32-year-old accountant, and a self-loathing 24-year-old musician. I also managed a date with a 29-year-old living with his parents, a Skype date with a photographer during which wearing a shirt was frowned upon, and four dates with four guys so forgettable I can’t even remember what they did for a living.

My dating disasters didn’t come without some reward. Early on I met a cute, successful businessman whose interests aligned with mine. When he asked me out again later that week, I didn’t hesitate to say yes. Unfortunately the second date’s dry conversation and lack of connection didn’t live up to the hype of the first. That, and his awkward fumbling through his pockets for his wallet when it came time to pay, had me less than interested to go back for round three. I paid for the first date, and you asked me out on the second: Be a gentleman and pick up the damn tab.

I blew him off after that. For a variety of reasons (and likely because I had yet another date to rush off to in 30 minutes) there were a handful of other guys I also blew off. It began to worry me.

Was I being too picky? Too focused on hitting lucky number 30 and missing guy number 18’s potential in the process? With no sparks flying and no one knocking me off my feet, I started to question if my entire premise was flawed.

Online dating was exactly like the bar scene: Either a guy was really into me and I wasn’t feeling it, or it was the other way around. I was putting myself out there as genuinely as possible, and expected more guys to do the same, not hide behind quirky profiles and Instagram photos. I often had to coerce guys into agreeing to coffee or drinks. It’s just like the bar. Everyone’s walls are still up.

Amid all of the disappointments—and being stood up, twice—the experiment was quickly becoming tiresome. I sometimes had two or three dates in one day; I began to feel slightly out-of-control and overwhelmed. Was love really worth it?

Guy #23 AGE: 32 HEIGHT: 6'1

THEN CAME THOMAS. He was 23, worked in medical sales. He wasn’t really my type—his slender body and light brown hair went against the grain of my standard type: 5’9”, dark hair, fit. Our cyber-flirting was playful and sarcastic. Yet I sort of had to nudge him into agreeing to a date.

We finally met for lunch. Two minutes into our conversation he reached across the table, took my sunglasses, and put them on. “These look better on me,” he said with an ear-to-ear grin. I liked that. A lot.

Over the next week we exchanged flirty texts without the standard shirtless and dick-pic fodder. This was the kind of electronic interaction I was hoping for from online dating, and I was getting it in spades via text messaging. I sleepwalked through other dates—a coffee here, a dinner there. In the third week of my date-a-palooza, it was all about Thomas.

For our second date I planned something romantic: an urban picnic with a view at Schuylkill Banks. The weather didn’t exactly cooperate, but it was still nice getting buzzed off wine in red plastic Solo cups. Once the sun went down I invited him back to my apartment five blocks away for more drinks—and, naturally, a hot make-out session.

When he left later that night, with only his shirt and shoes having left his body, I felt like I was making progress. I assumed a third date was right around the corner.

It wasn’t.

He went from being overly attentive to nonchalantly responsive. I tried repeatedly to book another date, but he was suddenly too busy to be bothered. After a few days of textual harassment, I eventually gave up. Aside from one explicit 3:15 a.m. booty-call text, I never heard from him again. Reality has a way of setting things straight—especially when it’s laced with a nasty dose of karma. Because what Thomas did to me was exactly what I had done to the cheap businessman and the others over the past three weeks.

I deleted his number.

MY LAST FEW DATES felt like one desperate attempt after another to fill the small void Thomas had left. I even booked another date following my 30th one—apparently the experiment had become an emotional bender I wasn’t ready to wean myself off of.

I went to dinner with Luke, guy #31 (I passed him regularly on my walk to work while he was standing at a bus stop along my route; we later bumped into each other at a party; I saw it as fate), and … oh, what does it matter? He wasn’t interested.

Since when had I become so needy, so committed to liking a guy without even knowing him? And why was I so oblivious to the signs telling me he wasn’t into me? After a day or two tumbling down a “What is wrong with me” rabbit hole, I eventually came to my senses. I stopped dating.

But the experiment didn’t end without teaching me some life lessons. You can’t go about finding love the way you go hunting for a tank on sale. The better things in life have to come to you when you least expect them. And despite your best intentions, sometimes you just want what you want. (Which explains how I ended up sleeping with two different guys on back-to-back nights. Ouch.)

But perhaps because I dated so many diverse guys, I also learned that maybe the best time to work on a relationship is before you have one.

And that Diana Ross was right.

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