I Dated the 26th President of the United States

Cassie Feldman
4 min readSep 7, 2019

Online dating can suck a dick. I’m serious. Online dating can heave itself into the nearest canyon. Online dating can pack its things, move to Hades and burn for all eternity.

I thought this time would be different. This app would be different. It had been a minute since I’d been on a dating app, but I thought, “Let’s give it a try. You’re not having a lot of luck on your own, and this is how people meet people these days. It’s either dating apps or Instagram (and your Instagram doesn’t even attract Russian bots).”

So I signed up, swiped, and matched with a 38-year-old School Counselor…a man who counsels the youth of this country. A man who claimed to love “fishing with my brothers,” and “attending concerts,” and “traveling to new places.” A man who had zero gym selfies, zero shots with a vintage Lamborghini, zero pictures of him giving a thumbs-up next to an exotic animal, and zero Machu Picchu vacay pics. This guy was perfect. Normal. He was an online dating sure thing.

And 30 minutes into our pinot noirs, that Sure Thing casually dropped the fact that he was once Theodore Roosevelt, the 26th President of the United States. I wish I was kidding. I wish he was kidding. He was not. (In fact, he got progressively angrier each time I questioned his seriousness.)

Apparently, when he was 16, he watched a documentary of Theodore Roosevelt. Then, he meditated (without drugs). During the meditation, he claims to have made contact with the soul of Teddy R. The Ted-ster then inhabited his body for an entire day. Which Teddy Roosevelt was he? Apparently all of them. He was baby Teddy, adolescent Teddy, Rough Rider Teddy, Mr. President Teddy, then old man Teddy. From birth to death, in 24-hours, he was Theodore Roosevelt. And I…was ready to end the date.

Was this the worst date I’ve been on? Unfortunately, no. I’ve been on a date with a man whose hygiene was so horrible it gave me acid reflux. I’ve been courted by 35-year-old who spent the better part of an hour crying because he didn’t know wasabi was spicy. I’ve been romanced by a fella who greeted me, dropped his pants, then said, “now or later?”

That caliber of bad date is uncomfortable. It’s jarring. It makes you question every life decision that got you to that moment...but those outlier experiences are far from the worst type of online dates. At least you get a story out of it. The worst online dates are the middle-of-the-road dates. The dates that go fine, with people who are fine, and conversation that is fine.

First you go on one fine date…then two…then five…then 17 fine dates later, something happens. You start to wonder if you’ve lost the capacity to feel. Or if your heart shrunk two-sizes-too-small like you’re some type of dating Grinch…because you should feel something. I mean, you went out with 17 people. Out of 17 people, one should have conjured some type of emotion. But nope, this newly gray piece of matter inside your chest cavity hasn’t changed pace once.

You think back to the past month’s activities: a haze of specialty cocktails and appetizer platters. A month of carefully selecting outfits and applying makeup to sleepwalk through another similar (yet different) conversation. You tally how many times you’ve disclosed the number of siblings you have, your hobbies, and your taste in music. You laugh at how you’ve said you enjoy hiking more times than you’ve actually hiked.

You wonder why you just wasted 34 hours of a perfectly good August.

You unlock your phone and hold your finger over this stupid app that’s tainted your weeknights. It shakes in fear, knowing it’s about to go to cyber hell. Your finger creeps closer to the “x” on the top left corner. One click and it’s all gone. But before finger-touches-screen, you stop yourself. You stop because you remember the last time, years ago, when you thought about deleting this app. You almost did, but you decided to go on one (or was it two?) more dates first.

You remember that on one of those dates you met a guy who seemed fine at first. Then, he cracked a joke…then another. And they weren’t particularly funny jokes, but you found yourself laughing. And not a normal light chuckle, like an embarrassingly steady stream of giggles.

Halfway through your mojitos, you noticed something different. Your posture was straighter. You were leaning forward. Then suddenly, you both reached for a sweet potato fry and your fingers accidentally grazed. Instantly, your heartbeat quickened. Your cheeks turned pink. You felt an electricity you’d been void of for 17 dates. It was like you were a dusty pinball machine that just got plugged in for the first time in years. And as the lights turned on and the sounds chimed, you realized that you weren’t broken. Your heart hadn’t disintegrated into a pile of charred ash. You worked just fine.

You remember thinking, “This was all worth it. All those dates were worth it.” And you hope this time it will be worth it too, because it only takes one person to light you back up. And that one person might have just messaged you.

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