The Crazy Lesson I Learned From Going On 80 First Dates
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  • Post published:30/07/2021
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Two years ago, I remember reading an advice columnist whose tagline was, “I’ve been on 76 first dates before I met the love of my life.” Her whole shtick was giving romantic advice to eager singles.

I was one of them.

I wrote into that columnist, let’s call her Sharon, lovesick and confused about my own vast array of single-related issues. She ended up heavily editing my sad story to the point of unrecognition. This “expert” stripped away all the parts that made my big question messy, and you know, realistic, and replaced it with a simple lady asking a simple question so Sharon (BARF) could give a simple answer.

If there’s anything anyone knows about Sarah E. Miller, it’s that she is not a simple woman. She intentionally adds a middle initial to her name for chrissakes.

I was livid.

Sharon, in all her 76-dates-of-wisdom, was just an idiot like the rest of us.

And now, after going on 80+ first dates with no end in sight, my earnestness and heartache are replaced with a lot of shoulder shrugging. I’m just kind of tired. Did Sharon the Advice Columnist ever experience profound tiredness? Or does she brush her long, silky hair in the mirror while recording herself giving advice to all her fans?

“Oh yeah, that’s good,” she’ll say to herself, as she puts on her ruby red lipstick, “I’ll tell them they must love themselves before they can love anyone else.” I imagine Sharon probably cackles into the moonlight like the two-bit advice witch she is.

The First 20

The first twenty or so dates, one could say I was an eager beaver. I tried really hard. I brought a magnifying mirror up to my pores, plucking eyebrow hairs as my life depended on it. You can’t catch a man with unmanageable eyebrows, I said to myself. Seems odd, but maybe it’s true. I also did a lot of nervous peeing and a lot of internet surfing for conversation icebreakers. I picked out black shapeless outfits. I wanted a man to like me for my personality first, but also because I’m mildly fat. Some men like “curves” and my curves were forever hidden under a lifeless potato sack until further notice.

Unsurprisingly, the more I dated, the more I realized how romantically shy I was. I never really understood how anyone could swap spit so casually. Shouldn’t we at least sign a waiver first?

“What are you looking for in a mate?” I’ve been asked repeatedly, by all of my friends and family members after yet another failed date. I used to try and describe some vague anamorphic blob so they’d get the boring picture. But lately, my answer is simply “chemistry” because how can anyone argue with falling in love?

The Second 20

After a few dozen dates, it was already getting repetitive, but in a way that was unlike other women dating men online. To date, I have received no unsolicited dick pics (thank you, I’m proud of myself too), and instead, a slew of men telling me that I’m too sensitive, too tall, too nice, too something.

I tried becoming more cautious and asking specific questions to weed out men who couldn’t handle weirdness or anxiety. Naturally, that didn’t work. Did you know everyone in the greater Seattle area has some form of anxiety? It’s the most relatable form of emotional pain, after all!

At this stage of the dating journey, I realized that people fell into two camps within 10 years of me: They want an instant-girlfriend/wife to pop out those babies, or they wanted a non-monogamous-no-strings-attached-hook-up. Where was the great in-between? Where were the subtle nuances of getting to know each other for a couple of weeks before making out over a shared piece of chocolate cake?

“No one likes dating a downer,” Sharon says, tip-tapping on her crystal-encrusted computer.

Meanwhile, the questions from family and friends kept rolling in, more concerned this time, and skeptical,

“Have you considered dating women?”

“Maybe you’re not capable of feeling love in that way.”

“Do you think you’re asexual?”

God, I could only hope.

Recently, I took the Kinsey Scale test, a test showing what your sexuality is from 1948. I painstakingly answered each question with great thoughtfulness.

Due to my perpetual failure in understanding the opposite sex, at 31, I thought maybe, just maybe, it could be explained by my sexuality.

There are so many unknowns, and a modified 1948 internet test about my sexuality was just the ticket I needed to really understand myself. What am I? Who am I? Let’s find out!

Nope, Sarah E. Miller, you’re just weird.

The Third 20

By date 50, I stopped taking meticulous notes about the dates. I stopped observing dudes as potential writing fodder. At this point, I had my fill of anecdotes to last me a lifetime. From strange to creepy behavior, I’ve seen it all. Also, I knew I was attracted to men of all kinds, but the shyness made it nearly impossible (and worse turned itself into skepticism and sarcasm) to genuinely approach anyone openly and earnestly.

“You just need to have more confidence,” Sharon was back, this time in weird lingerie made for confident, big-breasted women.

Meanwhile, the dates kept coming. Brian, Steve, Exedra, all came with a variety of issues, but there was something missing. Some sort of mediator between the vast sea of familiar-faced men (the same people were on the same dating apps for years at this point) and myself. It was like groundhog day for singles. Every day and everyone was the same.

“Hey, what’s up?”

“How’s your day going?”

“What’s your favorite thing to do on a Friday night?”

Lord, I don’t know Kevin, probably eat waffles in the dark if I’m being honest.

The Fourth 20 and Beyond

“Maybe you should take a break for a while,” the fourth wave of concerned advice came rushing in. It’s been about four years of on-and-off dating, with several months of “taking breaks” and “working on myself.” I’d delete all the apps and join a gym, and sweat out the loneliness by listening to psychology podcasts or meditate walking around a lake.

Sharon looked up from her martini, “You know, once you stop looking, they’ll find you.”

“Sure thing,” I say.

I think about all of the men I went on dates with. So many of them I was attracted to, physically and mentally, and they didn’t feel the same. Some men would tell me that I might be “the one” on the first date, and I never see them again. It’s like strange human puzzle pieces trying over and over to fit together. Nothing has fit quite right yet.

Several of my friends go on a couple of dates before finding their soulmates, while Sharon the Advice Guru found her man after 76 dates. So…where does that leave me after 80+? Sliding into home at 100? Where does it leave the other singles who are floating around aimlessly and perpetually for seemingly ever?

I guess we’re just going to be single, you know until we “love ourselves more” or something.

Sarah E. Miller is a freelance writer, dabbler, collaborator, and occasionally funny lady. Read more of her work on Medium.

This article was originally published at Medium. Reprinted with permission from the author.

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