Can an Excel Spreadsheet Help a Dating-Averse 40-Something Find Love?

Former Live Wire host Courtenay Hameister plays the numbers game.

By Courtenay Hameister April 22, 2016 Published in the May 2016 issue of Portland Monthly

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Does creating a dating spreadsheet make someone a bad person? Don’t answer that. Yet.

In 2014 I found myself in my mid-40s and still single. Like, really single. No-relationships-for-three-years single. Haven’t-been-in-love-in-a-decade single. There-could-be-a-small-colony-of-elves-in-my-vagina-baking-cookies-for-all-I-know-because-no-one’s-been-up-there-to-check single (though that would be a loud and delicious-smelling enterprise to hide, and thus seemed unlikely). It was, I thought, time to date again.

But where to find the men? I began with a humiliating but necessary public Facebook request: friends—set me up, give me advice, find me options! I resolved that I’d be up for whatever came my way. And that I’d approach this scientifically, in a methodological fashion I was convinced would help me avoid the emotional pitfalls that led, in a roundabout way, to imaginary vaginal elves.

Up to that point, I’d had only one real adult relationship. It had left me so heartbroken and raw that for years I cried whenever anything even remotely romantic crossed my path: an old couple holding hands in Forest Park, two dogs sharing spaghetti, a 5-Hour Energy drink commercial. I didn’t want that to happen again. I thought approaching the romantic market armed with an analytical spreadsheet would make me more objective, and any resulting relationship would be less likely to fail. Additionally, I could add the ability to freeze header rows to my Microsoft Office skill set. Win-win.

I set up categories, allowing for ratings on a scale of 1 to 10 in each, as follows: Smart, Funny, Finds Me Funny, How Attracted I Am to Him, How Attracted He Is to Me, Interesting Job He’s Passionate About, Good Conversation, Sex, Likes to Talk About Ideas, and My Overall Affection for Him. This may be where you make the “bad person” estimation. Rating a person on a scale from 1 to 10? How calculating. I mean, literally calculating. I suppose my only defense* is that I believe we all do this in our heads anyway, I just typed it into an algorithm.

I didn’t want a perfect score. I just wanted a tool more accurate than my rusty dating brain to help me make a choice that wouldn’t bite me in the ass later. Or, one that would bite me in the ass, but only if I asked it to.

I went on 28 first dates that year, all entered into the spreadsheet. I didn’t set out to have a particular number; I just told myself to put on my Big Girl Pants and get the hell out there.

Two dates came in direct response to my original Facebook request, both friends who hadn’t known I was single. Lesson learned: post more sly social media updates that clue people in to your singlehood, like, “I sure do look silly on this tandem bicycle!” or “I liked The Revenant, but I would’ve enjoyed it so much more if I weren’t so desperately lonely.”

Another single friend saw my post and recommended Tinder, which I found to be a dark place of hookups and brazen left- and right-swiping, even more shallow than my spreadsheet. I did meet one very sweet polyamorous lawyer via the app, however. His sex score was off the charts, but on our first meeting he talked at length about HIPAA requirements in relation to e-mail correspondence. I realize that doesn’t sound very interesting; you might be surprised to learn it’s even less interesting than it sounds.

OkCupid was the catalyst for the majority of my dates. I sifted through literally thousands of pictures of men standing on mountains in hiking gear. Or skiing gear. Or holy-shit-is-that-Everest-base-camp? gear. I am not the outdoorsy type; I even listed “hiking avoidance” as a hobby in my profile. So in the Northwest, I was an outlier. Even so, I managed to find more than 20 Portlanders who didn’t a) have a tent-building tryout on the first date, b) have gluten allergies, or c) already know me. (In Portland, you will see friends and acquaintances on dating sites. The plus side is that it’s similar to seeing them in a brothel or an Arby’s—the mutual mortification will keep your secret safe forever.)

And I definitely made up for my sexless 20s, ticking things off my bucket list that had never even been on there in the first place.

I dated two polyamorous married men who defied my ill-informed preconceptions by being as interested in emotional relationships as they were in physical ones.

I had my first (and second!) one-night stands, which seemed out of character for me at the time but which I see now as a dating rite of passage.**

I went to Build-Your-Own-Burrito Night at Ron Jeremy’s sex club, wherein the big shock of the evening was that they ran out of tortillas.

I attended a fellatio class in North Portland wherein I learned that the proper etiquette after accidentally grazing your classmate with your practice dildo is to bow slightly and say, “Apologies. Playing through.”

I realized that I didn’t have to date someone very long for it to sting horribly when I found out that I rated lower on their figurative spreadsheet than they did on my literal one.

I discovered I had a preference for the tall and the bearded (the second a virtual requirement if you’re dating men in Portland). But also that humor, passion, and great conversation trumped everything when it came to the Overall Affection category.

On December 26, I had my 28th first date of 2014. He was tall, handsome, soft-spoken, and ridiculously smart. At the time, his scores were in the top three for the year. But he wasn’t the highest. Still, after our third date I knew I didn’t want to date anyone else. And if I had updated his scores as we dated, things would have changed considerably.

In March, we had an escapade that would have ratcheted his sex score up to 10.

In April, after I straight-up peed my pants in his kitchen during a mortifying coughing fit, his score for unflappability went off the charts. I’d forgotten to include that category. It’s surprisingly important.

And in the summer, when I went through a weeks-long anxiety episode that left me feeling broken and too crazy to love, I learned that he was deeply kind and even more forgiving. Neither of those were on my spreadsheet, either.

Other categories I’d left off: thoughtfulness, gratitude, physical affection, slightly waking up and making a sweet “Mmmm” noise whenever I make him the little spoon, and an encyclopedic knowledge of Gerald Ford’s “Halloween Massacre” cabinet reorganization in 1975.

Looking back, it was clear that my spreadsheet idea was flawed for at least three reasons.

One: Rating people on a scale of 1 to 10 in a romantic capacity is simplistic, reductive, and, if I’m honest with myself, kind of gross. It makes me feel especially dirty now that there is someone I deeply love on the list. I’m a grown-ass woman, not a frat-boy villain in an ’80s movie. Two: It’s impossible to make objective judgments about people you’re interested in romantically. As I revisited my scores, I noted I’d given one hot guy a stellar conversation score. Months later, I talked to him again, and it was one of the most awkward conversations of my life. Lesson learned: never let your libido fill out your dating spreadsheet. Third, and most important: Our feelings about people change as we get to know them. I never knew the ways I would grow to love #28 when I first met him, and I’m happy to learn new ways all the time. (Recent lesson: excellent spider killer, though squeals like a little girl. Utilitarian and entertaining.)

Besides, as I finally learned, if we’re smart about love, the last thing we’re doing along the way is keeping score. 

* Massive rationalization

** Let’s be honest—one of them was a dating rite of passage. The other came about because he was cute and funny and staying in a really nice hotel and my car was locked up after hours in a parking garage. I hate cabs. And I’m a whore.

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