Going on one bad date every six months was not helping my odds of finding something lasting. Photo / Getty
I asked the exact same question of every single bride who hired me to work their wedding as a professional bridesmaid. It wasn't about their biggest wedding-day fear or how much money they had left in their budget. I asked how they met their fiance.
Part of me wanted to know because it was a great way to kick off a conversation with a stranger who was hiring me to be their bridesmaid for the day, and part of me wanted to know for my own selfish reasons. For most of my time in this job, I've been single.
Their answers were part of my research on how they managed to find the one thing I couldn't wrap my arms around without it slipping away from me - a loving and supportive relationship. I figured that hearing about their meet-cutes would give me enough inspiration and motivation to stop rolling my eyes at dating.
But after a while, their answers started to fall into three main buckets:
• The ones who met their match back in high school or college, an opportunity I clearly missed.
• The ones who met them at work, which wasn't going to happen to me since I was running a business of one employee (me!) from my living room.
• The ones who met through the modern-day fairy tale of swiping right on each other's profile. I had tried that, again and again, without any luck.
By asking that question over 40 times in two years, I hoped that I would hear an unusual answer that would somehow magically end my long-running reputation as the "single one" in my group of friends. Quite literally, I was always the bridesmaid but never the bride.
It finally happened, last February, when I found myself sitting across from a new bride of mine at a coffee shop on the Upper West Side.
"So, tell me, where did you and your fiance meet?" I asked, wondering what bucket her answer would fall into.
"I gamified dating," she said, sipping her hot chocolate.
"What does that mean?" I shot back.
"I decided to join JDate and go on four dates every Saturday. I made a spreadsheet. Ranked guys by my preferences and narrowed down my pool of guys into a top five and then picked the best one. It only took me a month to meet my fiance."
"You went on four dates a day?" I asked, wondering how she had the stamina.
"Yes. Each date was 30 minutes. After it was over, I'd walk around the block and come back inside to meet my next date."
Here I was, talking to someone who treated dating like you might would treat shopping for a car. Yet I was intrigued by her technique. It seemed like an exhausting but fun challenge. I wondered if I could survive it.
"It is a numbers game," she told me.
I knew she was right. Going on one bad date every six months was not helping my odds of finding something lasting.
After our meeting, I spent the subway ride home re-downloading dating apps I had deleted. I was going to commit to going on 14 first dates during the month of February.
I set some rules: I would say yes to every guy that asked me out, and I had to ask out guys whenever I felt the urge to meet them in real life. No date could be longer than 45 minutes, and if after the first date, I wasn't excited by the thought of seeing them again, I would turn down the offer of a second date.
Two days later, I found myself on date one, with a guy who spent most of our time together looking down at his phone and then back up at the TV screen. When 45 minutes passed, I politely asked for the check, went home and arranged first-date No. 2 for the next night. When Saturday arrived, I had scheduled four dates for that day, each at coffee shops just two blocks away from one another. The first date of the day was with a guy much older than I was, leaving us with not much to talk about. The second date was with a die-hard Donald Trump supporter who spent the date pretending to be his campaign manager. The third was with a guy who talked to me only about Uber's business model. The fourth date, well, I practically was asleep by then.
The next six dates weren't any better. There was a guy who showed up late because he was doing drugs, a guy who spoke only about how much money his parents had, and a guy who kept talking about how perfect his ex-girlfriend was.
After I made it to the end of February and the end of my 14 dates, I wanted to text my bride and ask why this experiment worked so well for her but not for me. Instead, I logged into one of the dating apps, erased my profile, and searched for the "delete" button. I noticed I had a new message from a guy named Adam. Our match was expiring in four hours and we hadn't spoken yet. He messaged me his phone number saying that if I saw this before our match expired, I should text him.
"No way," I said out loud. I wasn't so keen on texting a guy first. But then I remembered that it was only March 1. Why not go on date 15?
It has been about 11 months since I met Adam at a coffee shop on a cold March day. I remember walking in, sluggish, thinking about the many awful iterations of how this date could turn out. But then I ended up thinking to myself - as we chatted about live music, the best pizza spots and, of course, my job as a bridesmaid for hire - that there was something different about our conversation. It didn't feel like just another first date. I had stopped looking at my watch and we were way over the 45 minute mark. We sat in that coffee shop for three hours.
I remember leaving that day, not sure if there would be a second date, although I hoped there would be. I finally understood that love is a numbers game. One where I must keep putting myself in front of new people until finally I find one who feels a bit different than the rest.