Yet Another (Ahem) Epic First Date

March 25, 2025 by Andrew Small No Comments

I just had yet another (ahem) epic first date.

And by “just had,” I mean that it happened at some point in the past eighteen months. I never write about anyone shortly after an “epic” date actually took place. In order to, you know, avoid life destroying hurt feelings and all that jazz.

Also, by “epic,” I mean that it left me questioning whether dating was worth doing at all.

And by “first,” I mean that it was definitely our last date.

Hm. I guess I could have just started this post out with: around 18 months ago, I went on a terribly crazy first date. But where’s the fun in that kind of terseness?

Anyway, I met this woman on a dating site because… who actually meets people in real life anymore?

She was gorgeous. We laughed over messaging, a lot. We both spoke each other’s sarcasm language. The whole thing had “rest of our lives” potential written all over it. And by “rest of our lives,” I mean that it had amazing first date potential.

We met. She was just as pretty as all her pictures, so long as I only looked at her through multiple filters on my camera phone. Honestly, I had no idea it had become so easy to make oneself look so impossibly out of my league with the tap of a few buttons on our phones. This isn’t to say she wasn’t pretty. She was just very… different, and it made me a little bit sad she didn’t feel comfortably posting actual photos of herself to begin with, because she was definitely naturally very pretty.

We talked. We laughed. We ordered coffees.

Then I found out she was a convicted felon, and had only been out of prison for a few months.

Okay, whatever, people can change. Listening to her story made me feel she was quite the different person. I decided to give her the benefit of the doubt.

“This may sound crazy, but can you take me to the mall to grab this thing I need for work tomorrow?” she suddenly asked, apologetic that our date would be interrupted by such a thing.

“No problem,” I said, honestly okay with it. A little driving around and window shopping would just be more chance to get to know each other.

We drove to the mall. We went to a clothing store. She started trying on clothes and took a huge armful of really expensive items to the checkout counter.

“M’am, this card has been declined.” She grabbed another. “This card, too.” She put most of the clothes back, except for a $250 jumper that looked like someone magically turned a potato sack into something sexy. Still declined. She turned to me and asked if I could loan her the money until she could figure out the card problem.

I paid for her new clothes, and we…

Whoa. That was a test. Of course I didn’t pay for her new clothes. At this point my red flag radar was pinging like crazy. This girl had spennnnnding problems.

On the way home she confessed that she had tens of thousands in credit card debt, and began crying as she lamented over how difficult it was to find a rich guy to help her pay off her accounts.

So, I paid off her accounts, and we…

DOUBLE WHOA. That was also a test. Of course I didn’t pay off her credit cards. Besides, she said “rich guy.”

I did, however, driver her back to her car in an *attempt* to end the date.

Except, she couldn’t find her keys once we got there.

We tore my car apart, looking in every nook and cranny. They weren’t anywhere to be found. At this point, I just really wanted to ditch her and be on my slightly less-crazy way.

We ended up driving back to the coffee shop and then to the mall. We traced our steps. Nothing.

Back to her car.

She found her keys. There. Inside her car ignition. Somehow the thing hadn’t been stolen.

Bye bye, epic date. Have a great life. I hope you find your rich man, I thought, as I drove away and removed all evidence of her from my phone.

And… to home I went. And… to bed I went. And… to sleep I went.

At 3AM my phone rang. It was from an unknown, but local number I didn’t recognize. I hung it up. It rang again. Again, I hung it up. The third time it rang, I picked it up. “Hello.”

It was her. In hysterics. She was completely panicked, crying, desperate for help.

I don’t remember her exact words were, but they went something like this. “I owe a guy some money (GIANT SOB), and he’s coming after me (EXAGGERATED WAIL), and I have to give him like six hundred dollars right now (BURST INTO UGLY CRY).” I just lay there in shock, saying nothing. “I am afraid of what will happen if you don’t help me out of this,” she blurted.

So, I went to the ATM, I pulled out some cash, and I drove to whatever loan shark was threatening to break her legs. I paid off her…

TRIPLE WHOA. C’mon people. That was also a test. A big one, too. As if.

Instead, I cut her off. “I’m sorry, I’m not the one to help you. Call the police.”

And… I hung up. I silenced my phone. I stewed for a while, and eventually went back to sleep, wondering if my refusal to help would lead to some poor convicted felon’s ultimate demise.

Don’t worry. She didn’t die. She messaged me the next morning to apologize and to ask if I was interested in date number two.

Long story short, I wasn’t.

But I was definitely thankful for yet another epic first date story to tell.

Yeesh. Dating. I still love it. Always have. Always will.

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