I Went on 30 Dates in 30 Days, and Here's What Happened

Updated on 4/6/2019 at 9:20 PM

"Who has time to find that many guys to go out with?" Rayna Greenberg and Ashley Hesseltine mused as we sipped coffees in the West Village last Fall. The duo hosts the hilarious podcast, Girls Gotta Eat, which is full of raw and relevant humor that hits on exactly what it's like to be a single millennial lady in New York City. At the time I was interviewing them for an article on dating trends in 2019 and simultaneously contemplating a move from San Francisco to New York. I asked them about dating experiments and they shared an idea they had to challenge themselves to 30 dates in 30 days, that they ultimately decided was more trouble than it was worth.

Challenge accepted, I thought to myself.

This comedy duo's throwaway idea piqued my interest. I imagined this was a great way to get to know a new city, hit the ground running on my romantic life in the New Year, and test my dating prowess. I knew I could do it on my home turf, but could I possibly find 30 eligible bachelors to date in my first month in a new city?

With only one way to find out, I decided to make the move official. I landed in Manhattan and started the clock immediately. It wasn't easy, it was only sometimes fun, and it turns out, Rayna and Ashley were right to scrap this idea. By the end, I was exhausted, disillusioned, and considered swearing off dating altogether, but the important thing is, I made it. Here's what happened.

I Set a Dating Intention

Once I realized the magnitude of what I'd gotten myself into, I decided to set an intention to keep myself accountable. I wasn't going to start swiping right just to make my number, so I resolved to approach each dating prospect with integrity. To me, that meant saying yes only when I was genuinely interested in someone and keeping my typical dating behavior patterns intact. I wasn't going to start initiating conversations or asking guys out. I still had to let them come to me, and still be myself through the process. It worked, it still got me to my goal, and I confirmed something I already knew — you don't have to be aggressive to get a guy (or 30) to ask you out, you just have to be very active on the dating apps.

I Got Very Efficient

I never would have made it without mastering the art of the dating doubleheader. To pull this off, I'd simply book my first date as a happy hour near my office, and leave after one or two drinks, saying I have to keep it an early night. I'd preschedule a Lyft, which helped ensure I left on time and kept me from paying surge prices unexpectedly. I'd make sure the next date was near my own neighborhood so that as long as I stuck to my two-drink maximum for each date, I was blissfully asleep in my own bed by 11. Some might wonder if this was a bad idea, but I found it to be a win/win. Either it wasn't a match and we both got out of there without wasting time and money, or it was a match and both parties couldn't wait to see each other again. It turns out leaving them wanting more was a great way to make sure the second date got booked in a snap.

I Learned to Embrace Speed-Dating

Speaking of doubleheaders, I knocked out nine dates in a night by using a service called CitySwoon that arranges a more modern, fun take on meeting people IRL.

The thing about speed-dating is that it's a great way to practice small talk if dating makes you nervous. That wasn't my issue, but I found it to be a helpful exercise in determining what I was actually looking for. For example, the cutest guy at speed-dating asked me out for a second date and I was downright giddy. But then on date number two, I realized he wasn't a match for me at all — he was just, you know, the cutest guy at speed-dating.

I Found a Way to Celebrate the Highs and Lows

It was going great with the very handsome elevator salesman until he pronounced it "cabaret sauvignon" and tried to titillate me with culinary knowledge, explaining, "Wine goes good with cheese." I was willing to overlook his elementary wine lesson, but he made it pretty clear he wasn't interested in anything too long-term. He looked me up and down and said, "You're gonna love New York, you'll for sure get hit on all the time." This might discourage a lady from putting herself out there, but I thought to myself, "I'll take that as a compliment, sir, and thanks for the wine. I'm off to test your theory."

Another guy asked me to dinner but then only ordered us oysters (yes, for literal dinner, oysters only) and then drank a bottle of wine by himself and, when the bill came, said, "Well, someone's gotta pay for this." It gave me a great opportunity to congratulate myself for always bringing cash on dates so I could quickly pay for myself and perform a speedy exit.

Then there was the charming intellectual who owned his own place, played guitar in a band, and shared my love of gin and witty banter. He was sophisticated, handsome, friendly, and after we parted ways, I never heard from him again. So I celebrated the fact that high-quality eligible bachelors are to be found in Manhattan and moved on.

I Remembered How Much I Love Being Single

Around date number 25, I was getting tired, and that's when I realized no one should do this. I'd been out with half of New York and I wasn't finding anyone to love, I was just finding more and more reasons to love wearing sweatpants. By the time I was listening to date number 30 explain how many degrees he was from Kevin Bacon, it dawned on me that as much as I adore dating, forcing myself to perform this weekly hat trick was taking the joy out of meeting new people. I got home from my last date, slid into my sweats, ordered myself a pizza, and wondered if I'd even learned anything through this experience.

Last year when I interviewed "Millionaire Matchmaker" Patti Stanger, I asked her about goal-setting when it comes to dating. "Love is not a numbers game," she reminded me. "If you approach your love life the way you approach your work life, you're going to disrupt the flow of the universe and squeeze it to death. You can't be in control of every little thing and if you pretend you are, you may end up ruining the magic." I didn't listen to Patti, and instead I tried my hand at 30 dates in 30 days. Was it worth it? If we're measuring success by whether or not I made it, sure. I met the goal. If worthiness is measured in finding someone to love, then I suppose Patti was right: I ruined the magic.

That's OK though. I know I'm better off alone than with the wrong person. As far as what's next for me, I may take a dating hiatus and treat myself to some solo time in NYC. Without a stacked calendar and all my time spent swiping, perhaps I'll find out what happens if I stop orchestrating everything so much and just let the universe do its thing.