Some Questions I Have During The Work From Home Date I’m Currently On

Some Questions I Have During The Work From Home Date I’m Currently On

In the midst of my St. Patrick’s Day drunken stupor, I managed to meet and start talking to a girl. Intelligent, funny, good taste in music, and very easy on the eyes. I don’t know how it happened, I don’t know why it happened, all I know is that I wasn’t going to question it and hope for the best.

Since I’m working this weird second-shift schedule, the only times I’m really able to go out on dates are weekends. Lucky for me, she was free last Saturday night. Everything was falling into place. That is, until Friday morning, when we both remembered that we had promised to hang out with someone else on that same night.

I’ll be honest, I was bummed out. I was pretty excited to grab a whiskey ginger at some divey-type bar that wasn’t a real dive bar, but at least looked like one so that she might think that I have some edge. I figured this was it, that it was over before it started.

And then on Sunday, she texted me while I was at brunch to let me know that she was working from home tomorrow (today) and that I was more than welcome to come over.

So I did. And I’m here now. And I have some questions. Namely…

What the fuck am I supposed to be doing right now?

I don’t have to be at the office for a few more hours, so technically, I don’t really even have to be working right now. But for some reason, my work laptop is open on the couch next to me. I just keep refreshing my email, waiting for a crisis to happen.

Meanwhile, she’s had two conference calls and signed a bunch of documents. The word “audit” has been said so many times. I’m not actually sure what it is that she does, but I feel like it’s probably something important. Who knows? I might have just found me a sugar momma.

Should we be drinking?

We aren’t currently, but, like, I’ve become pretty conditioned that when it comes to first dates, you should be drinking some sort of alcohol. Whether that alcohol is wine, beer, liquor, or weird fermented tea that you got from a yoga instructor, it helps loosen you up.

Sure, I’m supposed to go to work later. But at the same time, I feel like one or two couldn’t hurt. Maybe I can sniff out a bottle of red and play it by ear.

(Note: I just was informed that I “won’t be able to sniff out a bottle of red here because there are no bottles of red here.” Interesting.)

What should I be talking about with her?

I hate asking people about work. I really do. You spend 40 hours of your week doing something, the last thing you want to do is talk more about it. But when the basis of your date is exactly that, what else is there to talk about.

Sure, I could probably make it cool. Say something like, “You’ve said the word ‘audit’ several times. What are you being audited on? Or are you auditing something? Please explain.” But what if her job is boring? What if it put us both to sleep?

Is it rude of me to be typing this up while she’s sitting across the couch from me?

I don’t think it is. She’s doing her thing, I’m doing mine. I look busy. At this point, I’ve mastered the “stare intently at your laptop screen so that it looks like you’re doing something important” face. Maybe I should just put that to use here.

But at the same time, I should probably let her know that I’m writing about her, right? Or would that make things weird? I’m definitely over-thinking this.

What is the process for making a move on her?

I’m not saying that we have to do anything serious, but like, we’re on the couch with the tv on low in the background on a dreary day in Chicago. This is prime make out weather. My only concern is that she might be filling out some sort of important document that I have no comprehension of, and then just get annoyed with me for distracting her.

Or maybe she won’t. We’ll just have to see, I guess.

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Using sarcasm as a defense mechanism since 1993. At any given moment I'm either tired, drunk, or stressed out. Get at me at or whatever.

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