“Hey Jamie…” I said sheepishly. “Do… do you want to get drinks sometime?”
She looked back at me, smiled, and said, “Yeah, for sure. How’s next Tuesday after work?”
To backtrack a little bit, I recently decided that I’m going to get back into the dating game. Maybe it’s because my mom thinks I’m gay, maybe it’s because I’m just bored with getting hammered on the weekends. Either way, my company just hired on a new group of trainees, one of which really stood out to me. You see, I work for a tech start-up, so we have all the “cool” office policies. Catered lunch. Ramen on deck. No dress code. You know, like if a college kid started their own company.
That last piece is particularly important. No dress code allows people to be themselves at work. Well, when I first saw Jamie (that’s not her real name, by the way) I thought she would be an interesting change of pace for me. Quintessential hipster clothes — black skinny jeans, army boots, flannel, beanie on her head… really nothing too eccentric, but enough to show that she’s making an effort to not be thought of as basic.
The more I talked to her, the more I realized that we were interested in the same things. Music, exploring the city, food, and more importantly, getting fucking hammered. I took a few days to build the courage to ask her out and figure out if it’s cool to date coworkers with my company (it is), and finally asked her out in a manner that could only be compared to the nerdy kid asking the cute girl to the homecoming dance in a 90s teen drama.
All of this in mind, I think it’s important to address the whole “don’t dip your pen in company ink” concept. I know it’s a bad idea. I know it ends terribly (most of the time). It’s not the end that I care about. I like the middle part. That’s the fun part. But if you read the title of this column at all, you would know that even the middle part of this wasn’t what it seemed to be.
Anyway, we were all set to go. We were heading to this burger bar in Chicago that Jamie had been hyping up. They had some special called “3 B’s for $15,” which meant you get a burger, the beer of the month, and a shot of the bourbon of the month, all for only $15. Yes, please.
When we walked in, the bar was pretty empty. We called ahead so our food was already being cooked. Waiting is for peasants and dammit, if this bar used three different kinds of meat in their burgers, we needed it immediately. (Note: In retrospect, I feel like this should have been seen as a red flag. It’s not that women aren’t allowed to recommend cheeseburgers. That would be ridiculous. It’s just, every time I’ve ever asked a girl to get drinks with me—ever—either they or myself recommend some kind of cocktail bar or sushi or something.)
The date was going fine. We told stories about where we’ve traveled to and told drinking stories and even got to the point of playing an intense game of “Would You Rather?” which culminated in her asking me, “Would you rather drink this entire pint glass of Donald Trump’s semen through a straw or have your dad cum on your face?” (Note: This probably should have been another red flag. If not for the fact that this human being actually was able to conjure that question and ask it with a stone-cold straight face, because I have never met a women who is so comfortable with saying the phrase, ‘have your dad cum on your face,’ in a public place, and kind of loudly if we’re being honest.)
We parted ways after splitting the check (probably another red flag, but meh. It’s 2016, we don’t need to argue about who picks up the bill) and did so without a kiss before getting into our separate Ubers. I was fine with it because honestly, we’re coworkers and this was a Tuesday, so we didn’t have a weekend to digest whatever happened. And so we went to work the next day. We talked. Gave each other music suggestions. Typical stuff to get you through the day.
At around midnight that night, she texted me and asked if I wanted to get lunch the next day. Almost immediately, I said yes. “This is awesome!” I thought. “She must be really into me if she’s asking me to go to lunch.”
The next day came and we left the office in her car to head to lunch. We went to some non-descript diner around the corner and got some mid-day breakfast food. When we started eating, she looked down at her food and looked back at me.
“Hey, can I ask you something?” she asked.
“For sure. What’s up?”
“So…this might be kind of awkward because I know we’re still getting to know each other…”
This was it. She was going to tell me she had a crush on me, ask if there’s any chance we could date, make this official. Were we moving too fast? Probably. But fuck it. It’s Cuffing Season and I needed to show my mom once and for all that I’m not gay.
“…But last weekend I went to this lesbian bar with my friend and met this girl there. We really hit it off and I’m just…when should I text her? It’s been a few days, you know? I’m just really bad at these things.”
“Wh—what?” I stammered.
“What did you think I was going to ask?”
“No…no I just…” I was stalling. Should I tell her I thought we were dating? Too risky. I work with this person. “I just didn’t know there was a lesbian bar in the city! But yeah, you should definitely shoot her a text! Say hey! Get drinks!”
As much of a bummer as this was, I’m kind of happy that it happened. I would much rather have her tell me at lunch in the middle of a work day rather than after I got shitfaced and tried to kiss her at her doorstep. I guess now I just have another person to get drunk and explore the city with. Plus, one less thing to worry about coming back to bite my ass at work.
Oh, well. On to the next one, right? .