My first foray into the world of being a career woman began in early 2011. I started working for a large company (who shall be left unnamed).

The heady mix of being in an office, having a desk of my own, not wearing a maniform (aka uniform made for men) on a daily basis, and, of course, a crop of gentlemen for me to ogle.

I met James when he started at the company, a few months after me. As he was new, cute, and seemed friendly. So I made friends.

He’d stop by my desk to say hi after fixing someone’s computer, share stories with me, and make fun of me when I completely fried my computer multiple times.

A good beginning, it seemed, for a sweet little office flirtation.

Cut to two years later, it’s January, and I was talking with a co-worker about the movie Top Gun having been re-released in IMAX.

James was around for some reason. Usually, he was looking for an excuse to not be back in the IT closet at the back of the office. And he overheard our conversation.

“That sounds so cool!” he said.

“I know, right?” I looked over at him. “We should totally go see it!”

He made some sort of noise that may have been considered an agreement, but I didn’t push since some kind of emergency came up, and I had to get back to work.

But about an hour later, an email came in: “Hey Ash, we should totally go see Top Gun, what do you think?” James’s email asked me. “Sure! That’d be super fun,” I replied.

There was further discussion of plans, etc., and we agreed to meet up for happy hour before the movie. Please note: this was three weeks in advance of the movie screening.

Fast forward, to the night in question. I leave the office at five, but James has gotten stuck on the late shift, and can’t get out of the office until almost 6. By the time he shows up for happy hour, he’s got enough time to inhale some chips and salsa, a couple of tacos and a single Corona.

Now, to give him a lot of credit, in spite of showing up so much later than planned, he still refused to let me pay. Due to the tight timeline (there was only a single, 7:30 pm showing of the movie), we had to get over to the theaters. Where again, I was not allowed to pay for my ticket.¹

Now, we’ve discussed how I’m slow on the uptake at times. But I did clue into the fact that by not paying for anything, this had become a date. I hadn’t really considered James as a prospective candidate because we worked together, but hey, I was willing to start thinking in that direction at this point.

Anyway, we went to the theatre, grabbed some seats, and started watching. I love getting a chance to see movies I’ve spent my life watching on TV on the big screen. It turned out that James, a Navy Veteran, had been stationed on an aircraft carrier. So he had some fun stories and comments to include about how realistic (and unrealistic) the movie was.

We left the movie, and I felt like this was great. We’d had fun, shared some laughs, saw a movie, et al. For a not-quite-date scenario, I’d call it a success! We hugged goodbye and went our separate ways.

I was cautiously optimistic about what the next day would be like at work, and interested in what might happen next.

I’ll tell you what happened.

Nothing. Seriously. Nothing.

Over the next four weeks aside from the usual making conversation in the office, James did nothing. No attempts to hang out again, no clumsy pickup lines, nothing. So my brain sent him to the Friend Zone. And that was that.

In March, it was time to celebrate my birthday. I planned a big group dinner with a ton of friends and made a point to invite James. After all, we were friends, we still chatted at work, etc.

James comes to my birthday dinner, joined the crew, and we had a great time. Dinner, then moved to the bar for drinks. I proceed to get completely shit-faced.

Needless to say by the time it was last call, I was in no condition to drive. My roommate and I-- as well as some friends in town to help celebrate--had all driven together in my car. Somehow in the midst of this, I ended up standing near James, while my group of friends was divvying up who was going in which car.

“Ashley,” said my friend Kristen. “You’re going to ride with James.”

“Oh, yeah,” said James. “That’s not going to be a problem.”

Now, in my intoxicated state, I was able to look at this somewhat logically and come to the following conclusions:

I had arrived at the bar/restaurant in my own car
My roommate was driving my car back to our apartment
James lived in Tustin, and taking us back to my place in Costa Mesa was putting him several miles out of his way.
None of this made any sense.

I was incredibly confused. And I articulated this to (what I believe) is the best of my ability. But no, it was made very clear, James was going to drive me home, and that was that.²

So we get in the car to leave the restaurant and drive my drunk ass home. As we’re waiting at the first signal, I come to the awful conclusion that I’ve had WAY too much to drink and am about to be sick.

“Pull over!” I said to James. “I’m going to throw up, I need to get out of the car.”

So he makes a U-turn and pulls over on the side of the road. Pacific Coast Highway. At 2 in the morning. So that I can puke all over the sidewalk of a bus stop. It was an incredibly classy moment for me.

Somehow, after I’ve thoroughly embarrassed myself by getting sick everywhere, James has fucking Gatorade in his car for me. Like he was oddly prepared to be dealing with a drunk chick. (Seriously, that’s highly suspect). At this point, I was sitting on the curb, again at 2 am on fucking PCH, and apologizing. I was incredibly embarrassed.

It’s never fun to be that girl, ya know?

And James looks at me, puts his hand on my back to give me a hug and says “It’s totally ok, Ash. I don’t care. And if I'm honest, I really want to kiss you right now.”

To recap. I’m so drunk, I’ve forced him to pull over so I can be sick all over the sidewalk, in full view of him. But now he wants to kiss me.

Gross. Just gross. Like, a zillion times gross. I’m not sure if my face betrayed my internal struggle to not completely freak out, but I did my best. I looked at him and said “That’s disgusting. Get in the car.”

Not my finest moment.James drives me home and gets me inside, where I promptly dash to my bathroom to go get sick again.

I don’t have much of a recollection of what happened after this, but I know that I woke up in my bed, with my friend Andrea next to me. I was fully clothed and felt like ass. Par for the course for a night of drinking, right?

During that Sunday, as we all recovered, I received a couple of text messages from James, mostly blaming me for his hangover.

At this point, I was more concerned about how to handle this the next day at work. James was in the friend zone, and frankly, after the night before, he wasn’t moving out of it. (Yes, I remembered his comment about wanting to kiss me. Gross.) How to handle things, now that he liked me more than I liked him?

I’d never had to deal with something like this before, so it was definitely a flying by the seat of my pants scenario. I wasn’t sure how to handle seeing him at work but figured I’d just stick to the friend play.

The next day, Monday, at the office James made a stop by my cubicle. The embarrassment was so fresh in my mind at that point, especially the reminder of me basically yelling at him after he said he wanted to kiss me. Not to mention that he apparently was looking for signs from me as if to say “Hey, I know I puked everywhere and yelled at you, but I definitely want to go out again and see what happens.”

I kept things casual and tried to be polite, but I also wanted to make it clear I was busy and didn’t want to talk. I think he sensed something was up and he left.

Over the next week or so, I maintained friendly politeness, but made no encouragement whatsoever for him to stick around and talk to me, or anything that could be remotely considered “interest.”

It took this guy TWO WEEKS to completely flip out on me. I made attempts to be polite, replying to text messages, sending out friendly replies to “Hey, how are you?” emails when I received them, etc. But apparently, that wasn’t enough.

That’s when the texts started.

He sent a semi-aggressive series of texts asking “What’s going on? Why are you ignoring me? I don’t understand.”

I replied with a collection of canned responses. I said I wasn’t ignoring him, but that I was busy and while I enjoyed getting to know him, I thought we were friends.

But that wasn’t enough for him, apparently. After a few more days of my attempts to cool things down, he was having none of it. I had been deleted as a friend on Facebook.

Literally 14 days after my birthday event, a 1,000-plus word essay popped up on my Facebook Messenger on Easter Sunday.

I won’t bore you with a copy-and-paste of the message. Suffice to say if this had been the late 1700s, I would have challenged him to a duel for questioning my honor.

It was ridiculous and full of grammatical errors and typos.

And according to James, I was letting the best thing that could have ever happened to me go. He ended with wishing my family and me a Happy Easter. Incongruous much?

I read the whole thing once and realized there was no response I could give that would make this situation better, only those that would make it worse. There was nothing I could do at this point, and to be frank, I felt no need to salvage whatever James seemed to think there was between us.

But, if you ask him, I’m a bitch of the highest order. I’ll own it.

Now, I will totally own I was wishy-washy with him, in trying to avoid an awkward conversation and keep things civil. I will take responsibility for the fact I could have been more grown-up and said “hey dude, I don’t dig you. You’re great, but we’re friends,” and that likely would have stopped all this.

But hindsight is always 20-20. And at that point in my life, making the grown-up, mature decision was never my strong suit.

In the subsequent weeks at work, James made a point to not stop by my cubicle, but to stop by all of the other adjacent cubicles. He would hold pointed, loud conversations about how he hated dating in OC, and that the girls were all bitches. I did my best to just keep my back turned and ignore him.

My favorite awkward moment happened with James about a month after this all went down. I was in the kitchen brewing my morning cup of tea, and I was turned to face the doorway.

Literally, I’m staring vaguely out the doorway, and James walks in. Straight up, I kid you not, he sees me and turns around and walks back out the door.

I mean, I know that I could have handled things better, but seriously guy? You can’t even walk in and make a cup of coffee? Just ignore me and don’t say anything!

It was a rather ignominious end for James and me, especially when you consider we never really got started.

But fucking-a, after that fiasco, I made a hard and fast rule to never ever EVER date a coworker after James.

¹ TAKE THAT SPLIT-THE-CHECK-FRED!!!
² It later transpired that James had told a majority of my friends he had a crush on me. Hence their encouragement of his… suit, if you will.

James: The reason I don't date co-workers