What I Learned From Going on 50 First Dates by @50Dates_States - Smarter Dating
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What I Learned From Going on 50 First Dates by @50Dates_States

50 dates

What I Learned From Going on 50 First Dates by @50Dates_States

Every few years I look back on my former self, (for obvious reasons I’ve named her Past-Alicia) and laugh at who I used to be, what I used to think about the world, and the supposedly important events that dominated my thoughts. Recently, retrospect’s ability to make me blush at my own expense got a boost when I embarked on a new project: making a documentary in which I went on 50 first dates, one in every state.

From September through November I dated almost every day, under the big sky of Montana, with fall foliage as a backdrop in Wisconsin, during Hurricane Sandy in Virginia and even through a dust storm in Texas. I subscribe to “Do what you know” as much as the next girl, though sometimes I wonder if I should be thinking more along the lines of “Those who can’t do, teach.” With both those credos in mind, I’d like to share some of what I learned while going on 50 first dates:

Show Up (Even If You Don’t Want To).

Confession time: despite being what I called a “professional dater” I didn’t always want to try and connect with strangers. Sometimes days I’d be longing for a run while listening to a nerdy podcast and I had to go on a date instead. So I know how tempting it can be to flake when you’re feeling this way (or when you just had the worst date of your life the night before). Yet without fail, any time I wanted nothing more than to ditch all plans in favor of a bubble bath, I would wind up on some of the best dates of my trip.

Take my Utah date. I had literally turned to my producer mere minutes before arriving out the brewery we met at and said “I cannot explain how much I don’t want to do this right now.” (She gave me the stink eye and said “You’re doing it. That’s what we’re here for.”) Not only did I wind up on that first date with the guy, but he visited California after my trip was over and we went out more. Had I skipped the date for a solo hot tub session, I would have missed out on subsequent dates.

Speaking of Bad First Dates…Yeah, Those Exist For Everyone

I was probably a little naïve, but I didn’t know bad first dates existed. Yes, prior to the trip I’d been on dates that obviously weren’t going to lead to second dates, but never had I left a date thinking, “You must be freaking kidding me. That human being exists in the world?” Maybe I was sheltered. Or just blessed. No más.

There was the guy in Illinois who talked about himself only in a dull-as-dishwater monotone for forty-five minutes straight and didn’t let me speak.. And Ohioan who rapped and played the accordion as a type of woo-ing gestures. And the Delaware date who tried to hook up with me by offering to hook my producer up with his step-dad. Honest to gosh these things happened. But the good news is, you can leave.


The Only Thing You Owe a First Date is Kind Politeness

While on the road I realized one of my biggest flaws in dating: I always have felt I owed my dates something. The best version of me, the benefit of the doubt for hours on end, stifling my personality for their sake, or losing a game because I don’t want them to feel badly that I kicked their butt at skeeball. Totally the wrong line of thinking. All you need to offer a first date is reasonable kindness and politeness. If the date tells you he’s proud of swindling money out of a friend, you don’t have to just press your lips into a smile. Try asking what that says about his integrity – a conversation starter, not impolite, and perhaps highlighting a place of personal growth.

Questioning a Man’s Sexuality Will Not End in a Date

Pretty sure this one is self-explanatory, but I learned it the hard way in North Dakota. See, my original date backed out due to an emergency, and I found myself at the bookstore in the town of Medora (population 122). The mayor, who owned the shop, took me under his wing and had his wife start making phone calls to her friends in neighboring towns who had sons that might want to go out with me. I cold called a young man, explained what I was up to, and he hesitated. So I said “Hey, if you have a girlfriend…or a boyfriend…and you can’t do this, I totally understand.” In an effort to not assume the guy to be straight, I wound up without a date.

Have a Back Up Plan

First dates are practically the definition of unpredictability. Not being able to control outcomes is unsettling territory (at least for me). In order to give myself a sense of ease, I found having a back-up plan, or ten, to be extremely helpful. For example: do you know what you’re going to do in case your date flakes? I always plan to just go forth and conquer by myself (what’s up, midnight showing of Wrath of Khan?). That one’s easy.

But what about if you’re planning to eat ice cream in the park? You’re looking at a lot of weather dependency here, which means you want to know where you’ll head for shelter in case of a freak thunderstorm (ahem, I’m looking at you, Boston). Know where a coffee shop or bowling alley is so you can take cover and keep the date rolling. No, don’t look at your phone in the moment. Know! It saves you time, and the awkwardness of standing around trying to make a decision with a stranger (aka, your date).

Don’t Judge A Date By Their Cover (or Match Percentage, or Profile Pic)

My North Carolina date matched up with me at a rousing 68% – super low in the online datingverse. But he was cute and agreed to meet me for go-karting and I figured…why not? And the California guy clocked in at 71% (and had a corporate-looking profile picture. Past experience has taught me white-collar guys don’t usually like me in person). Both times, I was plum wrong about my first impression of the men online. NC wound up being one of the most meaningful and enlightening conversations I had on the road. And CA had me laughing in a way I never knew was possible over the phrase “it looked like a parrot.”

Here’s the thing about dating: You really never know who you’re going to connect with (or not connect with). All you can do is go for it, agree to meet someone in person, be human, and see what happens. That is one thing I’m pretty sure Future-Alicia will agree with me about.



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