The purpose for my hiatus from writing was that I had taken a hiatus from dating. My wallet hated me, my dog missed me, and I was missing some quality time with my bed and a thing called sleep. I’d like to say I’m well rested now, but that would be a lie. Sleep has always seemed like a convenience for the organized or lazy, of which I am neither.
I could write about my last date. It was the first in a while. There’s some heart-warming, gushy, feel-good qualities to the whole experience, but that’s not why you’re reading this. No, you want to hear how I explained my recent relationship history over the phone.
You see, when a girl asks something like “Tell me about your past relationships”, what she’s really asking is “How much baggage are we working with? How much of it do you expect me to carry?”
But really, at this point my dates and I are all in our late twenties. I mean, I don’t need anyone to help me carry my luggage. I need someone who knows how to operate a flippin’ forklift.
So my answer goes something like this:
…
Awe, screw it. Twenty minutes after starting the story, I was only a third of the way through. Story redacted, expect an episodic series of entries to follow. In the meantime, I command you to fall in love.
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It’s been a while. There’s alot I could talk about. There’s a lot I will talk about. But for now, I’d like to talk about… Talking. Or rather, the lack thereof.
I’ve been doing this online dating thing for quite some time. Sometimes conversation is easy, effortless. Sometimes it’s like pulling teeth. Well, more like someone else pulling my teeth. I’m not sure that first simile ever held water. Or teeth, for that matter.
Anyways, I sometimes wondered if I was doing wrong. But after a lot of dates, I’ve come to the conclusion that conversation failure isn’t my fault. It’s yours. I know that sounds self-absorbed, and admittedly, I love myself. Because I’m awesome. However, I’ve always been the guy to make people feel welcome, to break through the shy guy or gal’s walls of self-isolation, and make them feel part o the group. If we can’t have a good conversation, I don’t feel bad about it.
So after all this time, I decided to write up my theory on online dating conversation skills. Then I decided to draw it. Then I realized there are outliers. And then I thought about making the example more inclusive. Then I got bored, and decided to post my original work. Without explanation. Here’s the fruit of the lack of my labor. Enjoy.

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All good things must come to an end. Fortunately, so do mediocre things, terrible things, and even my ideas on how to effectively end sentences.
Yes, I’ve gone back to my “no consultants” rule. The conversation with Consultant Gal didn’t go as disastrously as I expected. We’ve decided to keep up familiar relations, and by the end of the evening she offered to pimp me to a few of her friends. I could think of this as a sign that she wasn’t super into me to begin with, but let’s face it. I’m flippin’ awesome and she was head over heels for me. I mean who wouldn’t be, right? I’ll count this as a wing man +1.
However, I seem to remember most situations like this going quite a different route when I was younger… Yeah, you know what I mean.

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At some point, the question I fear is coming. Hopefully not on the first date, hopefully not on the third… Hopefully not until the girl is stuck in a relationship with me, but it’s on the way. And my hopes will forever be dashed on the cruel rocks of reality.
Tonight, the question was served. I felt not unlike a movie character who has been served papers from some bummed out pot-head. Except, this question makes me feel like I’m the pot-head too. So I guess I feel like a pot-head getting served by a pot-head. And if that doesn’t sound like a half-baked sentence, then here’s the magic question:
“So tell me an embarrassing story about yourself.”
Now, usually social evasion/distraction is key at this moment. My most common strategy goes something like “Hmmm… let me think a minute. First off, have you ever tried [insert impressive thing I’ve done]?” Then the date says yes or no, and you transition into talking about the activity until they forgot how the conversation go to that point in the first place. It’s got a surprisingly high success rate. Try it sometime.
Anyways, for reasons long to explain, I couldn’t get out of this one. Which is a problem. Because my life is an embarrassing moment that has not yet decided to cease. Embarrassing moments have become commonplace, and I no longer find them embarrassing or have a talent for crafting these moments into stories. It’s like if someone were to ask you, “Hey, remember that last good breath you took? What was that like?”
I mean, really? What do you say to a question like that?
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A long time ago (three months), I promised myself I’d never date a consultant. And it was a good rule. But like all rules, I had to break it at some point! And I feel a sense of accomplishment at holding out for three months. Well, technically two, since my first date with Consultant Gal was about a month ago. Or… a month and a half? Well, let’s not break out the calendar, I have a feeling my proposed resolve would only continue to diminish.
So what’s wrong with consultants? Let me clear this up for you: a lot. They travel, they work crazy hours, they are always on call, and you never know when they’ll be whisked away on project for months at a time. Dating a consultant is just plain dumb. Which is why I say I work in IT, wait for the eyes to glaze over, switch to talking about my latest surfing trip, and avoid the whole being a consultant thing on a first date!
Anyhow, Consultant Gal is great. She’s funny, witty, attractive… all that jazz. Except she just got staffed to a project that’s an hour away and works on weekends. And being a consultant myself, I already drive an hour to and from work.
This may not be the end of everything, but I’ve seen better portends before (what am I freaking writing?). I’ve come to learn that, in relationships, I need to be the busy one, the crazy one, and the weird one. Yep, I’m screwed.
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Confession #1: I work in IT.
Confession #2: I can’t fix your damn computer. Get a new one.
Confession #3: I forgot that dates, like family members, think I’m a mother f***ing techno wizard just because I say I work in IT and “I can’t explain what I do”.
So I was on a date this week, and it was going pretty well. It started off a bit slow, until I remembered that I’m hilarious and should probably throw out a joke or two. Both jokes worked great, and before you knew it, there was a third and a fourth. And not all mine. And I even laughed at the ones that weren’t mine. Rather, I should state I genuinely laughed at her jokes. And let’s admit guys, we aren’t really laughing most of the time, just like she’s not… ummm… I mean I’ve heard stories that women lie or fake something sometimes, but I don’t know what that might be.
Well, things continued to go pretty well until about two thirds through dinner when we discovered we have a lot in common. Like a lot. Now this didn’t bother me, since I love talking about myself and hearing her talk about herself was kind of like me talking about me without any of the work. Yay.
Unfortunately, it made her a bit uneasy. In order to make things worse, I stated “Don’t worry. Like I said, I work in IT. I just researched everything about you ahead of time so that I could pretend to like everything you do.” That definitely made things worse.
Not so bad that I couldn’t secure a third date by the close of dinner, though. She probably only agreed because she’s afraid I’ll steal her identity and buy thousands of dollars of Japanese cartoon porn. But… a win is a win.
Confession #4: I can explain what I do, it’s just boring conversation on a date. Seriously.
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