Dating, humor

The Worst Kind of Date

I twisted the last strand of hair around my curling iron, staring into the bathroom mirror. Every time I did my hair, I felt like a teenage boy trying to unclasp a bra.

Okay. Not bad.

“Bing!” my phone sounded. I walked the short distance through my bedroom into the living room to check it.

“Hey! I’m so sorry. My roommate is in the hospital.”

Dennis, my 20-something Hinge (first) date for that evening, had just thrown me a curveball.

“Oh no! Are they okay?”

“Yeah, everything is fine. But I’m afraid I won’t make it tonight. I hope you’ll let me make it up to you.”

I chewed the inside of my lip. On the one hand, I wanted to sound supportive. On the other hand… I snapped a selfie and sent it.

“I’m so glad they’re okay! But you’re buying the beers next time because I did my hair and everything.”

“Aw man, you look so pretty. And absolutely.”

A few days later, we made plans to meet at a local food truck lot for happy hour. Once again, I stood in the bathroom curling my hair – one of my least favorite activities, but one that turned my fine, straight hair into something a bit more alluring.

Or so I continue to tell myself.

As I got ready to leave, my phone chirped. I looked at the screen and saw a text from Dennis.

“Hey, just got home. Don’t think I’m gonna make it tonight.”

My mouth sagged and tears pricked my eyes.

“Why?” I wrote back after a moment’s hesitation.

“Just not feeling it.”

My stomach fell along with a tear. My mind raced with a thousand things I wanted to say and continued to do so for the next 24 hours. Instead, I decided to say nothing.

“I’m really sorry about last night,” Dennis texted the following morning. I never wrote back.

“Of all my worst dating stories,” I recently told Henry, central Oregon’s last remaining gentleman, “the absolute worst was this guy, about a year ago, who basically stood me up – TWICE. The second time because he ‘just wasn’t feeling it.'”

“You’re kidding,” Henry replied in shock.

“I think it was social anxiety, but still. It REALLY hurt my feelings.”

This week, I received a new Hinge like. It was Dennis. A year after he’d stood me up. I finally seized the opportunity to say what I hadn’t said before.

Maybe I was wrong to lecture him, but I wanted to shake him out of his own self-centeredness. How many times had I rallied to meet a friend or first date so I wouldn’t hurt their feelings? Seeing Dennis on Hinge reminded me of a similar dating story earlier this year with “Craig Who Cancels,” one of the strangest dates I’ve ever had (and you know that’s saying something)…

“I’m actually a stand-up comedian,” Craig explained as we messaged back and forth via Bumble.

“No way!” I replied, gearing up to geek out on our favorite stand-up comics. After a few more messages, I invited him to meet me for Friday happy hour. “I’m going with some girlfriends, but it sounds like you can hold you own.”

“I love working a crowd,” Craig fired back, agreeing to meet me at the brewery at 4pm on Friday.

Around 2pm on Friday, I received a bizarre message:

My girlfriends and I attempted to decipher the confounding note.

“Maybe he has Covid and doesn’t want to say.”

“Maybe he panicked.”

“Maybe he started seeing someone else.”

Disappointed, I wrote Craig off and turned my focus to other activities and matches. A week later, and despite having my phone number, I received a new message from Craig on Bumble saying he had two extra tickets to a comedy show. It wasn’t clear whether he was offering both tickets to me or fishing for a date.

While waiting to see if my friend was available to join us, I switched our conversation back over to text messaging. Which is when things got even more interesting:

When I got to the comedy club, Craig greeted me with a hug. He was more nervous than any date I’d ever met, his voice trembling.

“Whew, I’m really blowing it,” he said, stumbling over the bartender’s name while trying to place our drink order.

Turns out the nerves were date-specific and he was a regular performer at the comedy club. He began introducing me to everyone in the small venue and I sunk inside my cold shoulder sweater.

Because I knew three of them.

Because I’d gone on first dates with them.

Apparently I have a type.

“Congratulations on a [recent promotion I saw on a Facebook group we have in common],” I said to Marty, an older guy I’d gone on a walking date with several months earlier (who then ghosted me after I turned down his second-date-booty-call proposition).

“Oh thanks,” he grinned, his overconfidence nearly balancing out Craig’s nervousness. “We went on a date in…December, right?”

My eyes darted over to Craig, whose expression I couldn’t read. “That sounds about right.”

Marty looked at Craig and raised his eyebrows.

“As I recall, I didn’t make it to a second date.”

I raised my eyebrows in return.

“That is correct.”

Unfazed, Marty chatted with Craig for another moment before flitting off to someone else; he was the MC for the night and clearly enjoying his role. For a small local comedy club, the show was surprisingly tolerable. Funny, even.

“I’ll call you,” Craig promised after walking me to my car at the end of the night.

I never heard from him again.

~*~*~*~*~*~*~

4 thoughts on “The Worst Kind of Date”

  1. Okay, all this is fascinating… if not slightly horrifying… history. But what’s the new scoop on Henry the gentleman? That’s the second date I need a blog about.
    😉

  2. Thank you for the great laugh! And the tip on how to end the date early if it’s not going well (“I think I left my oven on”) – a friend passed your blog link to me since I have just re-entered the dating world (albeit digital) for the first time in 35 years at age 56 (though I just got “carded” at the airport ordering a margarita).

    1. Oh my gosh, nice to “meet” you, Priti, and thanks so much for the follow! My condolences on re-entering the dating world, LOL This might not be the best blog to follow for encouragement…for nightmares, 100%. And high five for getting carded, my baby-faced new friend!

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