When Good Dates Go Bad

I know, I know, I suck at updates. It’s summer, what do you want from me?

Onward and forward.

The week after I met the wannabe cop, I made a drinks date with another guy I’d been talking to on POF.

As we both worked in the same area of the city, we agreed to meet up at a local restaurant for drinks around 5:30pm. It was a very warm day, and I stood outside, nervously passing time on my iPhone while I waited for my date to arrive.

Suddenly, someone was standing in front of me, and I looked up. He was maybe an inch taller than me (I’m 5’7”, and finding a dude taller than me is more difficult than you might imagine), with ears that stuck out a little, and a great big smile. He was very clean-cut and a little preppy, but still very cute.

“Hi!” he said.

“Hi!” I said back.

“Want to go in?”


He held the door open for me, and we walked into a VERY crowded bar. As there were no seats available, we decided to try the more casual restaurant next door.

The Prepster and I slid into a booth in the bar, and he suggested we split an appetizer.

“Nachos?” I asked.

“No. Anything but nachos. Why does everyone pick nachos?”

“Because it’s easy to share. Okay…spring rolls?”

He made a face, so I said, “Well aren’t you difficult, Mr. Anything-But-Nachos. Chicken fingers?”

“Yeah, I could do chicken fingers!”


We ordered chicken fingers and beer, and spent the next hour talking about everything from baseball (if you follow me on Twitter, you might have figured out that I’m a huge Toronto Blue Jays fan) to our worst dating stories. He even cracked a joke about how the first date is actually a job interview, and the second date is actually the first date, which is what I say all the time!

“So, this might be a little forward, and I’ll understand if you say no, but I have some errands to run, and I was wondering if you wanted to come with me so we can continue talking? I’d be happy to drive you home after,” he said.

I felt that the two of us were really hitting it off, I wasn’t ready for our “interview” to end, and I wasn’t getting any serial killer vibes from him, so I agreed. He paid the bill (one point for the Prepster!) and led me out to his car.

First we drove to a local mall so he could pick up hats for his office softball team, and then we drove to a park to pick up the team kit (schedule, softballs, etc.) He said we were supposed to find someone named Mike, driving a dark car.

“Wait, whoa. Parking lot? Dark car? This sounds like a drug deal.” I said.

He looked shocked and said, “What? No! We’re just picking up the kits!”

I laughed, “Yeah, I’m from the ghetto. I know a drug deal when I hear one. Those balls are going to be FULL of drugs, my friend.”

“You’re from the ghetto?”


“You don’t seem like you’re from the ghetto.”

“Just wait until I get mad.”

“You’re going to get mad?”

“If we get busted for a drug deal I will.”

He laughed, shook his head at me, and suggested we go for a walk, since “Mike” with the “balls” didn’t appear to have arrived yet.

We walked past the busy baseball diamonds and along a paved path, where a rabbit hopped across the path ahead of us.

An older woman came jogging around the corner and down the path with her earbuds in, screeching, “DID YOU SEE THAT BUNNY?!”

I smiled and said, “Yes, we did!”


The Prepster said, “Yes, it is!”

Once the woman had jogged ahead of us, we gave each other the “crazy” look, and started to laugh.

Back in the parking lot, we met Mike with the balls in the trunk of his dark car. There were other people picking up kits, so the operation was either legit, or Mike has some seriously stealthy distribution in Toronto’s west end.

We stopped at a sporting goods store to check out bases for his softball game, and got into a heated debate about the new Toronto Blue Jays logo (what? I’m a graphic designer. I’m very passionate about logos!)

The Prepster drove me home, and walked me to my door. “Do you want to go out on a real date?” he asked.

“Yes, definitely,” I replied, and gave him a hug.

“I want to kiss you, but I’m being a gentleman,” he said, smiled, turned, and walked out the door.


The next afternoon, my phone buzzed. Text message.

Prepster: Whatcha want to do on Wednesday? A nicer dinner place perhaps?

Redhead: Sure. Have somewhere in mind?

Prepster: Hemmingways perhaps? Good place for drinks.

Redhead: Never been. Works for me!

Prepster: Perhaps I’ll convince you to wear a dress out w me? I could even drive you home from work before we go out if its easier.

Call me crazy, but the dress thing rubbed me the wrong way. Dude had been out with me once, and was trying to dictate what I wore? He had mentioned that I should wear a dress for our first meeting, but I had assumed it was a joke. Apparently not. I smelled a fetish.

I took a poll among my co-workers and friends, and it was like the great divide. Half of them didn’t see anything wrong with it and told me to wear a dress, the other half thought it to be controlling and a little creepy, especially after ONE date. One brother thought it was really weird, the other thought it was no big deal.

Redhead: You seem to have a thing for dresses.

Prepster: Haha yeah I like dresses, think they’re flattering on girls

Redhead: I’ll think about it, but I’ll be honest, I’m more of a jeans and hoodie kind of girl.

Prepster: Yoga pants and tank top is fine too. The opposite extreme.

That was NOT what I said.

Prepster: Or dress :)

Prepster: So, we’ll have some drinks on Wednesday. I suspect you get all touchy feely when drunk like most girls. So I look forward to it. Hehe.

Wait, what?

Redhead: Hahaha. I’m not “most girls”.

Prepster: You laugh because I know you already…because I am right.

Prepster: I like a girl who goes for what she wants though and makes the first moves etc

Redhead: And I like a guy to be bold and make a first move, so stalemate, sir.

Prepster: Hmmm…we may never be intimate!

Redhead: Look at you with the assumptions!

Prepster: An assumption that you like to kiss boys you enjoy being around. Well its bold but a high percentage assumption. Id kiss you.

Red flag. This cocky douche was NOT the same guy I’d met and liked, and I was starting to have serious second-thoughts about another date.

Prepster: Haha sooooo….how many drinks until you invite me to your place?


Redhead: Hey now, what kind of girl do you think I am? We just met, and this will technically be our FIRST date.

Prepster: Bah, everyone has needs.

Oh, I don’t fucking think so. At that moment, I knew I didn’t want to see him again. He was making me feel like a piece of meat he just wanted to get drunk and bang (in a dress), so I ignored his messages for the rest of the afternoon.

The next morning, my phone buzzed. Text message.

Prepster: Hey! Nice disappearing act yesterday :)

I wasn’t going to reply, but then I decided to take his cocky ass down a notch, and sent a reply.

Redhead: Yeah, I disappear when I’m no longer interested. I’m not the girl you’re looking for. Good luck.

Prepster: What? Just like that? What did I say/do?

I never replied, and that was the end of that, until one night a few months later, when I asked Siri to call my mother.

Apparently my mother’s name sounds like Prepster’s name, and I realized too late that Siri was calling the wrong person. Frantically pushing every button I could possibly find to end the call while screaming, “NOOOOOOOO! NO, SIRI! BAD FUCKING SIRI! THAT’S NOT WHAT I SAID!” I finally just powered off my phone and leaned my forehead against the wall with my eyes squeezed shut, praying that I had ended the call in time.

Because I am obviously being punished for something really horrible I must have done in a past life, when I turned my phone on, I received a text message.

Prepster: What’s up?

Fuck, fuck, FUCK.

Redhead: Accident. Sorry.

Prepster: Too bad, thought maybe you had a change of heart.

Ugh. I didn’t reply, and Siri has not been allowed to dial a number since.

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