I had an affair with my boss

We originally connected on a gay social app


I was in the Twin Cities for the summer, and I was just looking for friends to pass the time with. My days consisted of sitting at a desk and answering phones for a call center. It was tedious work and I was desperate for a change.

I stumbled upon a man’s profile, who shall remain nameless, on the gay social app, Scruff, and saw that he started and managed a successful event planning business.

Messaging him in an attempt for an escape from the call center, I ended up becoming somewhat of an assistant while also managing the company’s social media presence.

One evening, he asked me if I had plans for the rest of the night. With nothing better to do, I agreed to a stress-free coffee date. He advertised himself as being in a committed relationship on his profile, but he never brought it up in conversation. I did not expect anything to happen out of our work relationship, so I didn’t think it was necessary to bring it up either.

We had talked at length over the phone and through messages, but I had no idea what to expect from him in person. From the beginning, he would slip in personal questions, that in other situations I felt would have been unprofessional or out of my comfort zone with a boss, but I did not read too much into it.

I admit that pulling up in his shiny black car compared to the usual beaten up cars  that my usual type roll up in, this was an interesting change of scenery. In many online meeting situations, the pictures are a false hope of what they really look like in person, but with him, it was better than what I expected. He was handsome, charismatic and his accent was definitely a perk, too.

Like most gay relationships, sexual or simply friendship, things tend to escalate quickly. We stopped by his office to pick up something after getting coffee, and after a silence between conversations, things escalated.

It may have been my own narcissism, the heat of the moment or a cocktail of both, but the fact that he was unobtainable, and my boss, quickly slipped my mind. I didn’t care that he was wealthy or well known in his career field, I was intrigued by the unfamiliarity of the environment. He felt experienced, and at the time I trusted his guidance.

Since my first job at the call center paid so well, I continued there while putting in extra hours with his event planning business. Throughout the workdays, I would get friendly messages on my phone or Facebook such as “how’s your day going”, “hope your day is flying by”, or “hope to see you soon”.

One night after work at the call center, he wanted to meet up and go over some goals regarding the social media accounts. Picking me up in his car, he withheld the detail that we would be going back to his house. Up until then, I had not even remembered the fact that he was in a monogamous relationship. It was already enough to process that he was my boss.

I have always, and still do, respect the boundaries of a monogamous relationship. I may have been in some school plays in high school, but pretending nothing was going on while shaking his partner’s hand may have been my best performance yet. In my own relationships, I have felt the serrated knife of pain from infidelity. I never thought I would be the one holding the blade into someone else’s back.

“This is my friend, Logan. He’s here for the summer and is helping me get the company’s social media presence going.”

The glamor of the job was intoxicating enough for me to forget about everything else that was going on around me.

The biggest event that I worked on with him as an assistant, was a wedding that ended up having a budget well into the tens of thousands. The reception was hosted at a 5-star restaurant that was completely covered with succulents and flowers arranged to those straight out of a fairy tale.

Typical wedding setting

With an open bar and servers floating around the downtown Minneapolis venue, the trays of wine helped fuel my awakened comatose.

Following the wedding, I was invited to stay with him at his Martha Stewart catalog furnished home while his partner was out of town on a business trip. I soon found myself putting down a bag full of clothes in their shared bedroom.

He promised me a day together doing whatever we wanted there or in the city. Calling off work “sick”, the excitement for the day was overwhelming. Of course, I expected one of those cute romantic comedy montages where the couple go walking through a park, skipping out of shops with a handful of paper bags, and a nice dimly lit dinner in a restaurant where price isn’t a problem. Instead, what I got was him constantly taking phone calls and reading a forgettable novel along the running path around a local lake as he went into his nearby office for client consultations.

The flashy glamor was quickly fading. Tiny details and mannerisms that I had overlooked until then were all that I could see while I was with him. I had walked through the hallways of his house numerous times before, but the lingering gazes of his partner in framed candid photos and posed portraits were inescapable.

While my time in Minnesota was quickly coming to an end, I decided to end things before they got even more complicated, if that were even possible at the time. While driving me home one night, I came forward with my intentions of ending whatever it was that we had together.

Having a flashy job is not worth ruining relationships over, and it definitely should not make you question who you are as a person.

By the time the epilogue of my summer came around, I got on my plane with much more than my luggage. The same glamour and beauty masked what was a chapter in my life fueled by ignorance and lust. A scarlet “A” might well be emblazoned on my forehead for the rest of my life, but I refuse to let a time influenced by immature curiosity define me as a person.

My name is neither Anne nor Monica, and I am neither mistress nor “man-stress”.