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I’ve Gone On 99 First Dates in Four Years and I’m Still Standing

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I never planned to go on 100 first dates. In fact, I never planned to date again, because my boyfriend Zach and I were going to get married. We had been together for three years, we were in love and on the same page about building a life together. Our wedding would be on a beach, and we would settle in on the west coast near his family. Life was finally happening!

Until it wasn’t. Zach abruptly broke up with me during a fight. He left my apartment, refused my calls, and a week later sent me a breakup email. Shocked? Yes, me too.

I endured the normal break-up emotions of depression, anger, anxiety, and the normal break-up activities of crying, drinking wine, eating ice cream, talking to a therapist, talking to my friends, and drinking more wine. After about six months I felt ready to get back out there—into the New York City dating market—which, of course, was now dominated by online connections. I created an OkCupid profile, chatted with guys, and went out on a lot of “dates.”

I say “dates” because they felt more like meet-ups, hang outs, or job interviews. I didn’t find a boyfriend but I did find many stories—good, bad, silly, ridiculous stories. My friends couldn’t keep track of which guy went with which story and eventually neither could I. So I wrote it all down on interweb.

100 First Dates is a project I started four years ago after my breakup, and I used it as a reflection tool, a way to help me digest and learn from my new experiences—and hell, it was much cheaper than therapy. One hundred seemed like a nice round number, and honestly, in my wildest dreams I never thought I’d actually date 100 different guys.

My younger, over-confident self believed that I would meet someone amazing within the first 30-40 dates (via OkCupid, Match, How About We, or in person), we’d fall in love and get married. I pictured us lounging on a warm Fijian beach on our honeymoon where we’d cheers our piña coladas to the fact that I never had to suffer through 100 first dates because he’d found me. Then we’d jump into the turquoise water and kiss passionately while a dolphin swam by.

As you may have wisely guessed, that lovely scenario did not happen. I have been on 99 first dates with 99 different men. I dated some of those men more than once, I fell for some of them, and a few others led to short-term relationships. But it turns out the most important relationship I fostered was the one with myself.

And surprisingly, this dating experiment pushed me outside my comfort zone in so many ways that spilled over into other aspects of my life. I learned so much about who I am, what I need, how to express those needs openly, and how to not take things personally…

For instance, I could have cried when one guy dismissed me from our date after 40 minutes—while I was in mid-sentence! Or I could have felt ugly when a guy explained how open he is to dating all types of women—really hot ones and overweight ones. (I did not ask where I fell on that spectrum.)

I didn’t get offended when another guy said I should feel lucky he asked me out, because he doesn’t usually date white people (to clarify, he was also white). When, at a speed dating event, a guy who chatted with me for 10 minutes had no recollection that we’d already been on a date from OkCupid a few months earlier (at that same bar!), I could have gotten angry. When a brunch date asked me if the beauty mark on my hand was cancer, I could have given up on dating altogether. Because nothing says romance like cappuccinos and cancer talk.

I realized early on that these guys’ bad behaviors were their problems and not mine. Instead of letting those awkward situations affect how I felt about myself, I chose to write about them and turn them into funny stories.

I’ve also had some wonderful dates with interesting, smart men who made me laugh and made me feel sexy, and reminded me that dating can be fun. Writing about those experiences helped me crystallize the qualities I’m looking for in a partner.

And in another shocking twist, the project also connected me to people all over the world—it even helped people. Female readers have told me that my stories helped them feel less alone in the world of modern digital dating, while male readers have thanked me for giving them some insights into women’s thoughts about dating and relationships.

For me, dating is a fun part of my life. I go out with friends, I watch movies, I try new restaurants, I do improv comedy, I date. It isn’t the end-all-be-all. I’ve learned I am my happiest, best self when I live in the moment and embrace the unpredictable. So yes, I’ve gone on 99 first dates. And I’m still looking forward to the next one.

In that spirit, I’ve launched an Instagram video contest to find my 100th date (details here). I have no idea who he will be, or what is next for me in love or in life, but I am fully open and ready. And in the meantime, if I want a frozen cocktail on a Fijian beach, I’m not waiting for a guy to join me.

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