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Cat and Mouse! What Happened When I Dated My Boss

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Cat and Mouse! What Happened When I Dated My Boss

It was hard for Jesse and I to decipher what were legit work issues or a couple’s quarrel.

It’s often said that dating a co-worker is a big no-no. If the romance fizzles, things can get awkward, take a bad turn or get downright ugly.

Despite these forewarnings, I found myself in a relationship with a co-worker who eventually became my boss. After digging myself deep into this big dating faux pas, I found myself putting in more overtime than this job ever called for.

When I first met Jesse I didn’t give him a second glance. I didn’t even know he existed until about the third week! At the time, I was completely smitten with another co-worker. Between my crush, Jesse and I, it was your classic game of cat and mouse.

Tom and Jerry Cartoon

I was the mouse (Jerry), my crush was the cheese and Jesse was the cat (Tom).

Eventually, the cheese went bad. Jesse and I, however, continued our game. And one day he finally persuaded me to go on a date.

PLUS: Single Gal Story: Dear Hunky Coworker

At first, I didn’t take Jesse very seriously. In fact, I didn’t want any co-workers to know we had been secretly sneaking off to spend time together during our lunch breaks. But then, as we started to talk more and bond at the job, I found myself  secretly hoping a coworker would discover us one day in the many hiding places we had christened ours. As for our jobs, as long as our relationship didn’t interfere with our work or become the source of water-cooler gossip, the rules were pretty lax as far fraternization was concerned.

Then, the summer dwindled down. My feelings grew stronger, and I was bummed to discover that Jesse and I would no longer work together in the same location. Jesse had a wandering (cat) eye so I was concerned I wouldn’t be able to watch him with his libido on overdrive. So I panicked. I had to find a way to spend more time with him while keeping my job and the cat and and mouse game going.

The fall season arrived and I noticed Jesse had become bored, so I continuously tried to keep him focused on my assets and not someone else’s. In doing so, I became less attractive and alluring and more clingy and possessive. I was constantly jumping through hoops and making sure Jesse was always satisfied and happy. I had become the cat and Jesse was the mouse.

I caught a huge break when Jesse was promoted and would be back at my job site. I would be working under him. “This is gonna be perfect,” I said to myself when hearing the news. I also promised Jesse that I would be “super professional” with him at work. He had a lot to prove, especially being so young and taking on a bigger responsibility.

Within days of the promotion and transfer there were many changes in our relationship. For one, Jesse implemented a strict no fraternization policy between us, so aside from me sneaking him lunches (yes, that’s right, I made him lunch everyday), I hardly saw Jesse. If he and I were going on a date, he asked that I leave work before him and wait down the block until he showed up. And gone were the days where we would talk about my day at the job. In fact, on most days, Jesse was so tired from work all he wanted to do was sleep and play video games.

Working with Jesse as my boss proved to be trickier than expected, especially when I had a problem or the slightest complaint. Not only was it hard for Jesse and I to decipher what were legit work issues or a couple’s quarrel, but I also grew more and more jealous and clingy, pushing him further and further away. And then I heard another girls voice when I called his office one day. All my morals and sanity went out the window. I went into work the next day as any woman my age would (I was 22 after all) and had nothing to lose. I was out for blood and went completely bat-shit crazy, causing a scene that Jesse labeled as damn near demonic. With his tail tucked between his legs, he was forced to call a truce, especially after I threatened to quit. Jesse also broke up with me stating he had “too much at stake” to lose.

MORE: Moving On When Breaking Up with a CoWorker

This heartbreak hit me like a ton of bricks. So a few weeks later I resigned from my position. Eventually, after sometime, I healed. I was back to my old self again – on the quest for a new slice of “cheese.”

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Tiffani is a true city gal, hailing from the concrete jungle of New York City. With a large coffee in tow (that’s pronounced caw-fee to my non-New Yorkers) this closeted “self-help” addict and Lifestyles writer is on a continuous quest to discover how to have the best romantic life. An old soul with new age sarcasm, Tiffani’s sharp, witty and tell-it-like-it-is attitude has resulted in many a snafu as she tries to navigate and conquer the most challenging and complicated assignment of all: dating the New York City man. Come a long for the ride as this seasoned serial dater tries to find balance between her journey to self-love and her old school values on dating and relationships. She writes about her lessons and adventures in dating as a twenty-something millennial and all the new rules that apply.


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