I Found Out The Hard Way Why You Shouldn’t Hook Up With Co-Workers

Sydney Kaplan
I Found Out The Hard Way Why You Shouldn’t Hook Up With Co-Workers
Photo: Cierra Miller/STYLECASTER.

I know, I know, there are rules about hooking up with co-workers, but imagine this. You’ve just graduated from college. You’re about to start a new internship at a well-respected PR agency in Boston (OK, actually in a dreadful suburb outside of Boston but I’m trying to earn your respect here). You’re excited for your future grown-ass life, a la Samantha from Sex and the City. But then you meet a charming Office Hottie at said internship who makes sure all of that innocent excitement for your future goes down the drain just as fast as you can say “f*ckboy”. Ah, memories! 

Let’s rewind, shall we?

I moved home to Westwood, MA for the three-month duration of my new sexy internship. On the first day, after what can only be described as a pilgrimage (the commute took almost two hours with trafficyes I want brownie points for this), I entered the building and was introduced to Ryan, the ‘Office Hottie’ I referred to above. He was twenty-five-years old, athletic, and totally nailed that whole preppy Boston look. I developed a crush on him almost instantaneously. Dammit. 

I was also given a “mentor” at work named Nick. He was Ryan’s roommate. Turns out, Nick’s girlfriend worked at this company, too. WTF?? Is this how the real world works? Are everyone’s lives so completely centered around their jobs that they only ever interact with their coworkers, to the point that they just say, screw it, we might as well live with and date one another, too? Seems depressing, but okay, Mentor! I trust you. 

Following my mentor’s lead, I proceeded to show up at Brahmin (a club in Boston) that I overheard Ryan say he was going to one Friday night. I figured I didn’t need to feel guilty pursuing a coworker when my very own mentor had done the same thing, right? Right?! 

Like any mature, self-actualized twenty-two-year-old, I completely ignored any and all red flags.

I dragged my sister to the club and accomplished Operation Stalk Office Hottie with flying colors—I found Ryan and we exchanged numbers almost immediately. He was super drunk and grabby, but like any mature, self-actualized twenty-two-year-old, I completely ignored any and all red flags. We’re all entitled to one sloppy night, I told myself. 

Cut to lunchtime on Monday, when between bites of my sad homemade salad (seriously, I wish Sakara had been an option back then), I noticed Ryan had messaged me on Google Chat to apologize for how drunk he was on Friday. I accepted his apology, and we chatted all day. Good thing I was the intern with barely anything to do! This chatter went on for a few weeks, and it was almost as if we had developed a full-on online relationship, all while sitting about ten feet from one another on a daily basis.

It was fun, a dirty little secret kept between us two, and it certainly fit with the fantasy Samantha Jones lifestyle I was trying to create for myself. After a few private hangouts and months of chatting and flirting via Gchat, Ryan invited me out with his friends in Boston. I dragged a friend along with me and we all met up at a bar in the South End.

By the time we got there, Ryan was already drunk. Okay, maybe Ryan’s Brahmin blackout wasn’t an isolated incident. And, wait, is that my boss? Funnily enough, the boss that I directly reported to, Alicia, was at the same bar. Alicia was 27 and happily married. Thanks to Ryan’s drunk wandering, it was fortunately not obvious to Alicia that we had arrived together—phew. I was happy to see a married gal enjoying a GNO, but other than that, I didn’t think much of our minor run-in. Boston is only so big, after all. 

My heart started pounding, my face turned red and I realized I hadn’t been Ryan’s only office affair.

Now, cut to the very last day of my internship. I walked up to my boss, Alicia, to say goodbye, only to find her hunched over her phone—like, as hunched down as one could be without actually crawling under the desk like a freaking animal—Gchatting none other than my Office Hottie, Ryan. My heart started pounding, my face turned red and I realized I hadn’t been Ryan’s only office affair.

Of course, all of my friends called me crazy for suspecting this, and when you’re called crazy enough times, you start to believe it. Eventually, I gave up my theory and went about my life like the boss b*tch I intended on being come graduation. 

During this time, I was also in a dance company. We had our show about a month or two after my internship ended, long after my fling with Ryan had disintegrated. I got to talking with another girl backstage who had worked at a PR agency in Boston. I told her about my PR internship, and when I mentioned the company by name, she said she had heard a crazy rumor about my team.

Apparently, a boy in my office had an affair with a married co-worker, and someone else in the office wrote this woman’s husband a note telling him about the affair, which resulted in their divorce. Well, that mouthful of a story sure sounded familiar. When I asked her for names, she said: Alicia and Ryan.

BOOM! I was right all along! This boy (and I use the word ‘boy,’ not ‘man,’ intentionally) was two-timing me with my own boss! And I can almost guarantee that it was my mentor Nick’s girlfriend who wrote Alicia’s husband the note that led to their divorce. Ryan always talked about hating her so much, but would never tell me why. The pieces were all coming together!

Whether I liked it or not, my eyes were fully opened to the world after learning about the messed-up love triangle (Or love square, if we include Alicia’s ex-husband, which we probably should?) in which I was blindly involved. So please, take it from this idiot—always trust your gut, and don’t hook up with your co-workers. 

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