What Happened When I Went on 100 First Dates
Originally published at www.glamour.com
What sane person wouldn’t be able to find real love long before reaching 100 dates? Uh…me.
The old me thought dating was a means to an end — a necessary-but-temporary state that we all must endure until we meet someone awesome who thinks we’re as awesome as we find him. We agree to be a couple and hold hands, get married, pop out a kid, and live happily ever after.
I was on that path with my boyfriend of three years. Sure, our relationship had its ups and downs like all normal couples, but we were in love and planning to get married. Then one night, we had a fight about him moving to NYC (we were doing the long-distance thing). He walked out of my apartment, and I assumed he needed to cool off. It got dark. I waited. He didn’t come back. Like, ever.
In fact, he never spoke to me again (save for the breakup email he sent a week later, only after I had to stalk his sister in another state to see if he was still alive).
I did what any recently single woman in her early thirties would do. I endured a good six months of breakup mode: sad crying, angry crying, wine drinking, ice cream eating, and angry yelling…and then I put myself back on the market.
Over the past four years I pushed myself outside my comfort zone to meet new men. I tried all the popular dating sites. I dragged friends to OkCupid trivia nights, speed-dating events, and single’s snowboarding meetups. I also met men the old-fashioned way, such as at a friend’s party or in a comedy class, and I allowed myself to be set up on dates.
I collected so many (mostly funny) stories that I started to record them on my blog, 100 First Dates. I thought it would make for a fun read at some point in the future, but I found writing a cathartic way to process my experiences. My anger, my heartbreak, my highs and my lows are all documented, and when I look back I can see how I’ve grown and changed since each moment in time. Yes, I officially hit 100 first dates, and wow, did I have some eye-opening and jaw-dropping experiences.
I had some amazing dates with cute, smart guys like Jeremy, whom I spent four hours with on our first date drinking whiskey on a cold Sunday afternoon. There was sincere and funny Gabe, who lied about his age to impress me (he was 10 years younger), who will always have a special place in my heart. We dated for a summer and are still friends today.
The lows, of course, made the best entertainment for friends, family, and strangers at cocktail parties. Like the guy who instructed me how to eat my food during our entire dinner, “You can’t put sauce on that!” (I did, and I enjoyed it.) And then there was the guy who went into unnecessary details about all the different types of women he dated — both “hot model” types and “chubby” ones, apparently. What luck to be on a date with such a Renaissance man!
I learned infinite lessons during the course of these 100 dates, the most important being that I learned to like and know myself. I really got to know who I am and what makes me happy. (I’m a positive, adventurous, curious person, and that’s what I’m looking for in a partner as well.)
I’ve gotten better at dating too. I no longer allow a guy’s bad behavior to affect me personally. Those are his issues that he can work out with his therapist. I no longer waste time stressing about things I can’t control. Instead, I take charge of what I can, like what to wear on a first date. The secret? Find a comfortable, sexy outfit and wear it over and over again. (One advantage of going on only first dates — no one will know!)
The old me was quick to judge new people and situations, so I purposely dated guys who were not my type — and was pleasantly surprised when we connected. In another twist, I also bonded with some of my female readers who reached out to me over social media, which led to in-person coffee, which led to in real-life friendships.
So while these 100 dates haven’t put an end to my dating just yet, they’ve been worth it. Dating, like life, is an awkward, fascinating, sometimes awful, and totally unpredictable journey. But there are beautiful moments, new friends, and lots of learning about yourself — and that’s one relationship that will last for the rest of my life.
Originally published at www.glamour.com.
