Damn, it Feels Weird to Date a Gangster

Submitted by Emily:

I met David on an online dating site.  He was a few years younger than me, which was fine. He worked in the advertising department of our local newspaper, and I had spent the past four years working as a news reporter. We chatted casually for a few days, and judging by the conversations we were having in e-mail, I figured we'd have a lot to talk about when we met up in person. I suggested that we meet up for coffee later that week.

David insisted that I come pick him up from his parent’s house nearly 45 minutes away, which should have been a sign that things would not end well. But he was cute, and with so much in common, it seemed silly to pass him by. I told him I wasn't comfortable with that, and that I'd prefer to meet him at the coffee shop.

He balked that he didn't know where it was and that he sucked with directions, and therefore Mapquest was out. I told him I'd meet him at the newspaper where he worked, then, and he could follow me to the coffee shop two blocks away. After another ten minutes of debate, he finally seemed fine with this, so we made plans to meet on Wednesday night.

When the time actually came to meet up, he showed up 15 minutes late in a beat-up Camry. He called to see which car I was in, and  I responded that I was in the only car that was turned on in the parking lot. He said that I had a yuppie car, and that he wasn’t surprised someone like me would want to go out for coffee. I’m sorry, what? I drove a ten-year-old Honda Accord. Whatever.

Still clinging to some amount of hope that things might go well, I had him follow me all two blocks to the coffee shop parking lot, where he parked next to me. He got out of the car and walked over.

He was dressed like a cross between a high-school Goth and a gangster, wearing over-sized black pants with bondage straps, a red ICP t-shirt, his ball cap on side ways, and a gigantic cross dangling from his neck. This was a pretty far cry from the pictures he posted online but, whatever. I could still give him the benefit of the doubt, right?

He asked, “So where is this place?”

I pointed to the centuries-old brick building behind us, an old market that had been refurbished and turned into a chic coffeeshop—one of my favorites in town.

He said, “You’re taking me to this dump?”

“It’s not a dump, just wait until we—"

“It’s too crowded in there.”

I surveyed the inside of the coffee shop through a window. There were all of seven or eight people inside.

“But there’s only—"

“And what’s with all the idiots and their laptops? God, it’s full of students bumming wi-fi on their computers. Pay for your own damn internet!”

“Well, would you rather go someplace else?”

He complained for another five minutes about my poor choice for a place to go on a first date before he explained to me where he wanted to go—a pool hall smack in the middle of the worst part of town.

I told him I wasn’t comfortable going someplace I wasn’t familiar with, but when he burst into a tirade about how I wasn’t being accommodating, I shut up and told him that I’d follow him there.

Needless to say once he drove off, I booked it in the other direction. He sent me about 50 texts calling me a wide variety of names. I blocked his number.


  1. Ironic that he complained about people using wifi when it looks like he was living with his parents and came to the date dressed like a loser. I bet by "advertising department" he meant "call center". Sorry he was such a dud, that sucks.

  2. Your date's a total tool, and you don't deserve that.

  3. Call center jobs pay crap and so crap people work for them so that is probably why this player had such a pathetic ride. Always look for red flags like that! He was lying about what he did for work.

  4. He wasn't lying about what he did, he was glorifying it.

    "I'm not a telemarketer, I'm in advertising."

    "I'm not a prostitute, I'm in human services."

    "I'm not a drug dealer, I'm a retail sales consultant."

    See? Easy.

  5. 1:31, LOL! Great comment!

  6. I never heard that about a prostitute before, Anon 1:31. I'm learning so much from this site -- yesterday dumpster diving at Goodwill, today about call centers and advertising... I'm so grateful to everyone...

  7. The best part of the story? "I shut up". If only it had stayed that way, I would have three minutes of my life not wasted reading this.

  8. 8:19, yeah, because your contribution was SO worthwhile. Dick.


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