When Playin’ It Cool Goes Wrong

Filed under : Dating Stories, Sad Stories

Story 1 of 365

Est. Reading Time 3 minutes

It was winter of 2005. I was working for Vivid’s web department, which was outsourced to a company in Woodland Hills, CA. I worked on a lean-and-mean team of less than 10 people. I was the only designer left. In addition : we had 2 programmers, 2 managers, 2 affiliate program heads, and another 2 guys whose roles I never quite figured out.

I got along well with the whole team, but me and the 2 programmers were particularly close 1they’re the ones to the left of me in the header image for this post. That’s helpful during “crunch times” like we’d often had. We went to lunch together every day, unless one or more of us had special errands to run.

One day, we’re at a Carl’s Jr. up the road from our office. We’re having our lunch, and I look over to see a beautiful tattooed blonde-haired girl with glasses. Just the right combo of punk-dirty and classy that I fall so hard for every time I see it. On the other hand, we’re in a damned Carl’s Jr. What am I gonna do – interrupt the poor girl’s lunch with my incessant yammering?

On the walk to my car, I came up with a plan. I handed my friend my business card and said “hey, drop this on her table and just be like ‘I think you and my friend would get along'”. He thought I was insane. But, he also had nothing to lose and a great opportunity to make fun of me to gain. So, he did it. Only.. I didn’t know what he said, he just laughed and said “I got the message across”.

Fast-forward about 15 minutes and there’s a new message in my MySpace inbox 2remember how much better MySpace was for dating than Facebook?. At the time, I listed my MySpace URL on my business card, much like today I’ll list my Twitter/YouTube/Facebook URLs. The message was from Hot Tattooed Blonde Chick With Glasses.

She said (something along the lines of) “your friend gave me your business card. said you were too chicken to say hi. But, I’m intrigued and you’re easy on the eyes, so… what’s up?” 3I feel like she ALSO mentioned having worked in the same building. Or maybe my friend mentioned seeing her. Somehow it came out that we worked in the ...continue.

This is where I fucked it all up. Another in a long line of “things I will forever regret doing”. I wrote back (something along the lines of) :

Is THAT what he was doing when he ran back in there? haha! I knew he was up to something, now I know. Anyway, I’m doing well – how are you?

My friend saw my reply and immediately smacked me upside the head – “DUDE! why are you pretending you don’t give a shit? Ask her out, idiot!” (or something along those lines). I told him I’d clear up the situation when she replied, and I’d further make fun of myself for being a douche in that first message when we got around to our first date.

But.. she never did reply. She clearly decided “well, this guy’s a douche” and moved on.

About a month later, during my yearly Christmas trip to Phoenix, I decided to hit her up and just be honest with her. I told her that what I did was a douche move, and for some reason I was trying to play it cool in the moment, but I’d love the opportunity to just go out for some drinks and hangout and that she’d be free to mock me utterly for my douchey ways.

Once again.. I got no reply. When I returned to work sometime around the first week of January, I noticed she hadn’t even read my message. I thought that was odd, so I figured I’d take a look at her page and see if maybe she was just out of town. And that’s when I found out why I’ll never be able to undo this mistake.

She died in her sleep, late Christmas evening while staying at her parents’ place for the holidays.

Was it a drug overdose? Accidental mixing of prescription drugs and holiday alcohol? Obviously, I’ll never know. Maybe I could’ve done nothing to prevent it. But, some part of me thinks if we hit it off, we’d have been texting like weird teenagers during the holiday and I could’ve been like “heyyy… don’t chase that percocet with vodka” or something.

In the end – I pulled a douche move that I’ll never be able to undo and she never got the satisfaction of mocking me in person for it.

Footnotes   [ + ]

1. they’re the ones to the left of me in the header image for this post
2. remember how much better MySpace was for dating than Facebook?
3. I feel like she ALSO mentioned having worked in the same building. Or maybe my friend mentioned seeing her. Somehow it came out that we worked in the same building, so that may have also been in her message to me