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Honest Confessions Of A Girl Who Hooked Up With Her Boss

Honest Confessions Of A Girl Who Hooked Up With Her Boss

Talk about offices romances and most of us will agree to have sailed in that boat at least once. But dating a boss? Well, been there done that too. Dating a boss can be complicated, especially if you have no idea whether his flirtatious hints are casual sexual advances or he is looking for something serious!


Before you start assuming that your boss is THE ONE, here’s my real life story that can help you figure things out better. It began when I started my new job as a copy editor in a well-known media house in New Delhi where Karthik (name changed) worked as the Assignment Editor. I had to directly report to him for all the news stories I would cover in the day. The first time I saw him, I was immediately struck by how hot he looked. He was 5’11′, with dark brown hair and eyes the colour of hazelnut. We had a brief introduction on the first day and I went back home and told my roommate about how attractive I found my new boss. She was quick to dodge off any possibility of me dating him in future claiming that he was off limits because first, he was my boss. Second, given that he was so hot, he MUST have a girlfriend.

Also Read About Office Romance

However, that didn’t stop me from thinking about him. In the office, I would never miss a chance to talk to him or gaze at him from the corner of my eye and back home I would fantasize about him every night. I was pretty confident that my feelings were inconspicuous to him or to the rest of the office.

Work and life went normal until one day when the management decided to throw a grand annual party for the employees. Well, at social gatherings like this, you will find me fixated at only one spot holding a bottle of beer, observing people. That day, while I was enjoying doing the same, Karthik came to me and offered a drink. Granted that this is pretty casual, I didn’t think too much of it. We began talking about work, how I was settling in and gradually the conversation moved to our personal lives. I was really enjoying the first heart-to-heart conversation with him ever since I joined the office. As more drinks flowed in, we lost track of how many bottles we were down and it didn’t strike me that I was totally tipsy. We made out that night at my apartment.


The next day at the office I was a little nervous but thankfully there was no talking about what had happened the previous night. In the days that followed, we kept things professional. We would talk about business when we were with others but in private we were all flirty and handsy with each other. We would spend the entire day chatting and sharing information that we wouldn’t otherwise with a colleague. I started looking for opportunities to spend more time with him. Everything seemed so great that I never felt I was making a mistake.

We hooked up several times after that, but always in my apartment. It didn’t really occur to me that Karthik never proposed hanging out at his place. Looking back, I realise I got so many hints indicating that something was just not right but I loved spending time with him so much that I overlooked everything.

A few months later, Karthik went on a sabbatical for a month. I was upset because he hadn’t told me and I came to know about this from a coworker. I called him up but he talked like nothing had happened. He told me he had a medical emergency in his family so he wouldn’t be coming to work for a month. At that point, it struck me that he had never talked to me about his family. I thought I will try to get him to open up once he was back.

A week before his expected return, a coworker casually told me how she had run into Karthik, his wife and their newborn at the mall the other day. It took me a while to process what had happened. I felt cheated and disrespected. So all this time, my boss was hooking up with me while his pregnant wife was waiting for him at home. I was furious at him for taking me as an option to satisfy his sexual needs. I was also angry at myself for being so stupid and developing feelings for my boss.

When Karthik returned, I knew I had to confront him. To my surprise, he replied, “Wait, are you saying there are feelings involved here? I thought you knew I am married.” He proposed that we catch up someday and “clear the air.” I refused. I knew this had to end. 

I decided to not share details about our relationship and his lies with anyone in the office. I was strictly professional with him then on and eventually resigned two months later. I am still not of the opinion that dating your boss is bad. He/she could actually be THE ONE for you. But it’s always preferable to stay on the safe side and take precautions before indulging in an office romance

Think Long Term

It is important to analyse how this relationship will affect your professional life in the long term. Know your office policies before you get into something like this if you don’t want to get fired for crossing professional lines at work.

Confront Him Early

Talk to him about where you are heading early on in the relationship. Both of you should be on the same page. Things can get complicated if he thinks of it as a fling but you are seeing prospects of something serious.

Create a Boundary Between Office and Romance

Even if you are dating your boss don’t ever use this as a leg up in your professional life. The affair should also not affect your productivity at work. Stay true to your career goals and remember that the company is paying you to do your job.

Don’t Become The Office Gossip

Everybody loves gossip, even at work. There will be people who would love to pull you down just because your boyfriend or girlfriend is the boss. Stay away from PDA and sharing too much about your relationship at your workplace. The ones who are friends with you now may stop taking you seriously (or even start hating you) if they find out that you are dating the boss.

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22 Mar 2019

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