Dating Your Female Boss: She Was His Boss And Now Asking Him Out On A Date

Dating experience | | , Author & Journalist
Updated On: April 17, 2024
Dating your female boss

Dating your female boss is often considered so scandalous that the secret is kept behind closed doors. You’re not going to find someone boasting in broad daylight, “I’m dating my boss”, because, in all probability, they are going to get fired.

So can you date your boss? Under what circumstances? If you’re one of those people who has fallen for someone in a senior position and you want to start dating your boss, continue reading Rita and Ron’s story.

How He Started Dating His Female Boss

Rita knew men fell for her. Tall, sexy and exceedingly well-spoken, she had risen to become the young editor of a lifestyle magazine. Some of her older junior colleagues wondered how she had become so successful at 28 years of age. A few insisted that she had had a ‘long office romance’ with the owner of the media house.

Luckily for Rita, however, most knew that she had got the job since she deserved it – and not because of some non-existent affair with a happily married owner whom she had met only once.

When Rita hired Ron, a talented like-aged man for the position of an assistant editor, neither of them could have guessed what life had in store for them. Ron realized that dating your female boss is in reality very common and not as ‘special’ as the movies showed it.

“We can pay you $5,000 a month. It is 20% more than your previous salary. That is the best we can offer, and not a 30% hike which you are looking for,” she had said matter-of-factly, staring at him as she spoke.

Ron was gobsmacked: both because of how gorgeous she was and the confidence with which she said those words. He had come across other bosses in his brief career, but the girl sitting in front of him was something else.

“I am okay with it,” he said without taking his eyes off her. He also thought, “I want to date my boss already”, but kept his mouth shut on that count. Rita left her seat, and so did he. He felt his limp palm crumble inside her firm grip as they shook hands. She smiled at him and said, “Welcome to our family.”

Some shared interests

Can you date your boss
Dating your boss really does take your mind off your priorities

Ron joined his new office a fortnight later. His boss introduced him to his future colleagues, who seemed friendly and relaxed. He had joined at a time when the magazine’s pages were supposed to be sent to the press for printing. It didn’t take him long to figure out that people were reeling under work pressure because the all-important deadline had to be met.

Rita and Ron used to mostly interact when she summoned him to her cabin. As they spoke, the two of them discovered that they shared two common passions – reading and movies. Gradually, both of them started discussing books and movies whenever they were relatively free.

“If you read so much, why the hell are you in journalism? Few journalists enjoy reading books, you know,” she purred in jest one day.

“But you are a journalist too, right?” He asked a little uneasily.

“Hey, tell me something,” she sounded serious all of a sudden. “You appear to be very friendly when you talk to your colleagues. Why do you act like one of those shy guys when talking to me?”

“You are the boss, right?”

“So what? I am just like anybody else. Let us talk as friends in future. Is that okay with you?”

She stared at him and grinned.

He murmured, “Okay, done.”

“Louder please.”

Both of them started giggling.

When Ron left the cabin, he had forgotten that the second-in-command had given him a deadline for submitting his article. One quick reminder and he buried himself in work once again. Dating your boss really does take your mind off priorities.

Let’s go to the movies

About a week later, Rita called him to her cabin and asked him whether or not he had watched The Curious Case of Benjamin Button, a recent release at the time.

“I saw it yesterday. What about you?” she asked.

“Not yet. But I will,” he replied before sharing his plan about watching it on coming Saturday.

“Please don’t skip it. I liked it a lot. You would too,” she said.

“Oh no, I don’t miss any film,” he said and quickly corrected himself, “Rather, I don’t miss any good film.”

“By the way, I have heard something. May I ask you frankly?”

“Please do.” Ron didn’t know what was coming his way.

“I believe there is some gossip floating around – about us. Have you heard any such thing?” He was getting distracted by her unbuttoned shirt and pencil skirt. He had always respected her for being a successful working woman and for all her contributions to the company, yet he couldn’t help but ogle.

A couple of his colleagues had started teasing Ron that Rita had the hots for him. But he chose not to bring it up, and said, “I haven’t heard any such thing. Have you?” Can you date your boss if people are already suspecting things? – he wondered.

“I know you have because some guys pull your leg occasionally,” she looked at him and winked.

“They are not serious about it,” he grinned sheepishly. He had been caught lying.

“Who will you watch the film with? Do you have a girlfriend?” she asked.

“No, I will be going alone. I am, well, single,” he told her.

“Would you mind if we watch it together? I want to see it again. You buy the tickets, I will treat you to dinner,” she said.

“Well, there goes my heart”, Ron thought, “I want to date my boss and she seems interested too.”

I want to date my boss

Dating the boss

Inside the theatre on Saturday, Rita whispered into his ears, “This is weird. I am your boss. We are out on a date of sorts, aren’t we?”

“Seems like we are.” His search for a few more words thereafter proved to be futile.

“I like you, Ron. Now, just relax.” She held his left arm as she spoke.

“So do I. You are the boss. But I do too,” he said.

The theatre was dark. Ron smiled at the thought that a beautiful presence had lit up his life – as he watched a story unfold on the screen in front of his eyes.

Related Reading: 12 Ways Office Affairs Can Spell Trouble For You

Rita and Ron went on to secretly date each other for six months before Rita’s boss found out and immediately sacked both of them. Ron realized why the movies portray dating your female boss the way they do. Well, because they never end well.

So if you’re planning to date your boss, make sure you follow every protocol and instruction to ensure that the romance doesn’t threaten your job and your career.


1. Is a boss allowed to date an employee?

To put it simply, no. Very few companies allow romantic relationships at work, and even if they do, they demand extreme professionalism.

2. How do you tell when your boss wants you out?

If your boss is making subtle advances, making more eye contact, touching you randomly, they’re probably interested in you.

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Readers Comments On “Dating Your Female Boss: She Was His Boss And Now Asking Him Out On A Date”

  1. Office romance is no cake’s walk, especially when it’s a boss lady and a male employee. But then we are humans at the end of the day. It’s not impossible to succumb to the longings of our heart. Attraction has its own way of operating on human mind.

  2. Office romance can go really South if there are any complications. I personally feel that one must keep their personal and professional lives apart. But then, you know, the heart wants what it wants ! Hope Ravi’s promotions do not depend on his career graph with his boss!

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