Should I Go Out With My Boss If He Asks Me?

To date my boss or not to date my boss. That is the question. Well, at least for some of us. So how does a rational, flesh and blood employee answer the “should I go out with my boss” question?

Let’s start by admitting that it’s not easy to find people to date. And sometimes you just have to take a chance in life. But if the employee would also like to keep their job, how do they weigh the benefits vs the risk of dating a boss? Let’s try to figure it out.

Wondering if I should go out with boss

Regardless of whether your boss actually asks you out, is that something you’ve been thinking about? And, if so, have you been sending out signals or cues of being open to this?

Why does that matter?

Well, sometimes these things evolve naturally over time in the workplace. As you get to know each other better and build up a common language and mutual appreciation. After a while, feelings can start to enter the picture. But it’s a natural progression.

Then again, if you get the idea first and start leaving breadcrumbs to your gingerbread house (yeah, I know that’s a bad analogy), your boss might start to view you in a different light. Most likely it won’t be about work ability.

And sometimes bosses (people) can be tempted — and excited — by the game alone. Without feeling the same fondness or protectiveness back toward you, as they might with a relationship that grows organically over time.

Back to “dating a boss” question

Clearly, each situation is different. And anyone who tries to tell you what to always do or never do should probably keep their advice to themselves. But whatever you wind up deciding, should your boss ask you out, at the very least you need to keep your own best interests in mind.

And … if you’re a woman, please know this one thing. It’s really important to think about this when you are deciding what to do. In a majority of cases, the woman gets the short end of the stick. (No innuendo intended.)

Women who have romances with their boss often wind up fired — or made to look trashy or stupid or just plain “girly” and simple-minded. No matter what they were told or promised. And certainly the same can happen to a man who is not in the power position.

Then again, some office romances wind up turning into life partnerships. It happens. Just not that often. In general, the romance fades, and at the very least things get mighty uncomfortable. And even if the employee isn’t fired, they wind up leaving to get a fresh start — somewhere where there are no remnant bad feelings or labels.

Should I go out with boss or not?

It’s a risk. Some may feel it’s worth taking. Or simply plunge into it without thinking of the consequences. But whatever you do at work, even if in secret, often gets out.  And the consequences can follow you well beyond this job, with references or people you run into one day elsewhere.

Imagine a job interview for a job you really want. One you’ve been trying hard to get for many months. Now, in walks someone who knows your “sordid” story. (And so often it gets told in that way, regardless of reality.)

Only you know if the risk is worth it. And only you know if the signals are strong enough — and not just attraction — to make it worth exploring further.

What if you decide to date boss?

Personally, if you’re wondering should I go out with my boss, I’d take it very slow — at least to begin with. And definitely do not flaunt a close relationship with your boss to coworkers.

• See if there is something there apart from any physical chemistry.
• Talk about your concerns openly, and see how the other person responds to your concerns.
• Get to know them as a full person — apart from work talk.
• See how they talk about family and friends and other people in general. Do they value them? Or do they badmouth them?
• Try to get a feel for the person’s view of life. And how they see themselves in the world.
• Do your best to remain yourself throughout — sharing real views and feelings. And don’t just try to be what they want. If it’s going to work, you both have to be real.
• If you decide that you want to get more serious, still try to take it slow.
• And, no matter how perfect it all seems, know that it may eventually mean you need to move on. That’s also being real.

And just in case you do need to leave

⇒   How To Quit a Job (Without Hurting Yourself)

 

More articles you may enjoy

Help! My Employee Has a Crush On Me

Pros and Cons of Flirting With a Coworker

Overly Friendly Coworker Wants To Be Friends!

My Boss Has a Favorite and It’s NOT Me

 

Why Is HR So Useless When You’re Being Bullied?

How To Deal With a Bully Boss

Why It’s So Easy To Get Mad at Your Boss

When Emotions Take Over In the Workplace