In 2018, I'm Going On 40 Dates To Break My Bad Dating Habits

No matter the scenario, I am a master at dreaming up the worst case of it. When I was a small child, I hosted nightly fire drills in my bedroom. I would practice scooping up all of my stuffed animals at once so as to leave no koala behind. Now that I am a bona fide adult, these worst case scenarios are more like, "The world is ending!" or "He's going to murder me!" and of course, the classic, "Everybody hates me!" Such sentiments are obviously problematic when it comes to dating, which is why I'm going on 40 dates in 2018.

Yes, I have committed to 40 appointments with strangers. But don't worry, fellow cynics, I promise I'm not one for New Year's resolutions. I find them unattainable at best and body-shame-y at worst. Resolutions are a great way to set oneself up for failure. Since I personally don't love the feeling of failure, I try not to make any promises to myself.

However, this past year, in an effort to defeat my self-sabotaging ways — and also, to attract some attention to my production company — my business partner and I started a podcast/experiment/challenge designed to get me to put myself out there more. It's called 51 First Dates (because copyright) and I currently have 40 more dates to go on in 2018.

Here's how it works: My BFF and co-host, who's in a loving relationship, picks out new and unique dates for me to go on. She has also set me up with her friends. Every week, I recap my dates anonymously, with no identifying details, and we only speak about them kindly. (The exception — date number three, who had two phones out the entire time.) We have delightful guests join in for discussions on themes like opening lines, sexting, and paranoia (my fave). Most importantly: the goal is not to find a relationship because relationships aren't necessary for happiness. The goal is to break my bad habits.

Throughout my twenties I've mostly been in "halfsie" relationships. I have dated people seriously, un-seriously, and somewhat seriously for periods from a few months to two years. Until now, I've never done the whole "swipe-until-your-fingers-are-numb" dating app scene that is so active in New York, where I live.

The few online dates I had been on prior to this podcast often went well, and led to "dating" if not dating. Even if I wasn't entirely enamored with the gentleman I was seeing, sometime around the third or fourth date, I would imagine the worst-case scenario: "IF HE DOESN'T WANT TO HANG OUT AGAIN, I AM UNLOVEABLE AND WILL BE ALONE FOREVER." Super chill, I know.

Which brings me to this 51 date undertaking. I've gone on 11 so far, and I'm going to on 40 more in 2018 — unless I start dating someone exclusively, in which case, we will recruit a single friend for the podcast. I'm going to continue going on these dates because already, after 11 of them, I can feel a change in perspective, especially when it comes to my bad habits.

Take Date Number Four. My date was cute, kind, and smart. We were from the same area of Massachusetts. As an added bonus, he traveled from Manhattan to Brooklyn (where I live), and picked out an excellent bar. We got along well — not fireworks-well, but well. Our conversation moved steadily, we both decided to stay for a third drink, and he leaned in to kiss me at the end of the night. Upon arriving home, I received a text from him about how much fun he had. I replied, and was relieved that my awkward first kiss vibes hadn't turned him off.

When I didn't hear from him the following week, I texted him innocuously about a TV show we both discussed. I didn't hear from him again. The podcast wasn't out yet, so he couldn't have Googled that. I definitely do not think that this date was "the one" — I just wanted to win. I spiraled into, "AM I THE WORST?" territory when really, it just wasn't a fit. Here's the thing: not everyone is going to like everyone else. Even if the love of your life ghosts you, however, that doesn't make you "unlovable." It makes them a jerk.

Remember how intimidating your first college class, or first day at work, or first time skiing, was? Remember how after you've gone to ten classes, or 20 days at work, or skied 30 runs, you feel completely differently? If you fall on your butt on your first ski trip, you might be tempted to say "I'M TERRIBLE AND I GIVE UP!" (Caps are used to enhance my inner monster voice, yours may be kinder.) But on your 30th ski trip, if you fall down, you're simply going to say "oops" and get back up again. Dating is just the same. By date 11, I've had three really excellent first dates that have led to second dates, so when one date doesn't go well, I don't immediately diagnose myself as "unlovable." And you shouldn't, either.

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