Flirting in the Workplace: It’s All Fun & Games Until Someone Loses Their Job (Unless You’re Tom Brady!)


CAUTION: This video might not be suitable for listening to in the office. Hit pause to keep it from rolling and put on your ear phones.


By J.T. O’Donnell

I saw this video years ago and laughed. But as an HR person, it troubled me too. You see, this video is spot on. Hot people often don’t get their advances on-the-job viewed as harassment, while less-attractive people do. In fact, there are plenty of studies that show good looking people get paid more and climb the ladder easier than those that aren’t.

Beyond that, here’s what concerns me…

Young people who are ‘hot’ in their early career and subsequently develop flirting habits they use to get ahead in the workplace could mindlessly carry this approach over later in their career when they are ‘not-so-hot’ and in positions of influence – and then, all of a sudden, it gets viewed as harassment. Perhaps, people see it as harmless in the early career years. Let’s face it, young workers often don’t have much to think about besides work and sex (yep, I said it). But, as we age in the workplace, there is an expectation of maturity – and there is often a lot more at stake.

Honestly, I have worked with clients who were accused and fired for sexual harassment. The HR laws are very protective of the person who feels they’ve been harassed. So, companies will often air on the side of caution and let the accused go to avoid a lawsuit. Some of these people are guilty. As we talk through the situation they come to realize how they were being perceived. Yet, at the time, they honestly didn’t see how what they were doing/saying was making the accuser uncomfortable to the point of harassment. However, I must also tell you that some were definitely encouraged into this behavior. They tell me story after story of how other people in the office were doing the same thing but weren’t accused. Meanwhile, they got caught and it cost them their families, their jobs and their self-esteem. You should know that many of them are not prosecuted. So, while they don’t have a criminal record, they still have to explain why they were let go from a great job with a great firm for sexual harassment – not an easy thing to do. It makes it tough to get re-hired.

Thus, as funny as the video of Tom Brady walking through the office in his underwear is, I hope you’ll consider the following: Be careful when flirting in the workplace. While you are in control of your actions, you aren’t in control of how your actions are being interpreted by others. I’m not saying you can’t be friendly with co-workers and may even end up dating someone special (although, please check your company’s dating policy first). In fact, I know of lots of wonderful work relationships that have turned into marriage. You are with these people for a 1/3rd or more of your day, so it stands to reason that you might find a love connection. I’m just saying that thinking you can say the same things to co-workers that you say when you are out at a bar trying to meet potential dates is not a good idea. And ladies, I’m not just talking to the guys here. Women are now a major force in the workplace. So, guess what? I’m seeing more harassment claims by men against women.

To sum it up, there is a very blunt phrase that states, “Don’t ___ where you eat.” Be sure to contemplate the implications of flirting/dating in the workplace. Beyond sexual harassment, there are lots of reasons why it might make sense not to engage in this behavior as it relates to your professional reputation.

HR folks – can you add more? Employees, what do you think? Share your thoughts below.


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  1. The first thing I thought of before reading the end of the post was exactly what you wrote, “Don’t ____ where you eat.” I have worked at a seafood restaurant since I was 15, now I’m 23, and there is always a ton of flirting going on between the staff. I definitely know where to draw the line at work because I don’t want to get fired over a sexual harassment suit. It’s just not worth it. Save the flirting for after work. Just don’t let the flirting go too far outside of the workplace because I have witnessed some bad and sometimes really awkward next days at work between people.

    I personally don’t think you should be dating anyone at work, especially if you are a manager and you're dating one of your employees. My boss was dating a girl that worked at the restaurant and he treated her very different than the other girls. I felt like he favored her and gave her special treatment, which I don’t think was fair to the other waitresses.

    • Josh – the restaurant work scene is a fascinating place. For those that haven't worked in that environment it can be really tough. It's a party atmosphere that often rolls into late nights, and as you pointed out, some interesting decisions that can make people feel wierd the next day. I cocktail waitressed years ago to earn money to go abroad for school. It was my first time in that environment and I saw waaaaayyyy too many things a 20 year old shouldn't have scene. But it was a valuable lesson too. Similar to you, the boss dated some of the servers (walked in on them by accident), and the late night behavior was scary. And the harassment I received from drunk people? Geez!

      Thanks for commenting (and for reminding me of that quote, I should have given you attribution in the post!)

  2. Being cautious of your conduct in a workplace environment is so crucial.

    If you catch someone on the wrong day and in the wrong mood, a simple compliment can be taken the wrong way and you could be sitting in front of your manager before you know it, trying to talk yourself out of a sexual harassment complaint.

    Reading this post reminds me of an episode of The Drew Carey Show when Drew is accused of sexual harassment from a co-worker for attaching a simple cartoon to the bottom of a memo. I believe it had something to do with a french fry flirting with a caterpillar. This is a quote from that episode

    Drew: (drafting a new memo) From now on, all employees will be required to bring their sense of humor to work every day. This replaces the normal practice of having a stick up your butt!

    Now since this is just a television show, this scenario comes off as humorous. I agree with Drew sometimes people just need to 'relax' but that's not how things go anymore in a workplace setting. Innocent actions like the one Drew had occur everyday and most of the time go without punishment. However, you still need to be careful of what you say and do. Even having your name mentioned in the same sentence as 'sexual harassment' can tarnish your professional reputation.

    Read this quote. It offers some great advice:

    “Know your audience. Some people may appreciate a dirty joke here and there, others won't tolerate them. Even complimenting a person's physical appearance can be tricky.

    “Someone who doesn't know you better could construe a well-intended compliment (‘That sweater really brings out the blue in your eyes’) as a come-on. Try to keep flattering remarks related to work (‘Great presentation today!’).

    “Bottom line: Play it safe. When in doubt, keep it outside the office.”

    Quote is from an article called “Is it OK to Flirt at Work?” and it was written by Mary Lorenz.

    If you do notice inappropriate behavior in the workplace, do you think it's better to approach the participants before raising the issue with management? Or is it better to go straight to management?

    • I think there is something to be said for your character if you find the right way to approach the parties involved. For example, I'd pull aside the person you know the best and say something like, “You know how much I enjoy working with you and I have a lot of respect for you. So, please understand how hard this is for me to share with you, but as a colleague who I value, I feel like I have to say something. Your relationship with XXX is causing discussion and distraction in the workplace. I don't want you to get in trouble or get a reputation that could hurt your career. So, I thought I'd just let you know so you could do something to contain the situation.”

      I think most people would appreciate having it shared like that. And the ones that react angrily clearly don't see what a good friend you are.

      From there, I only suggest going to management if the relationship is negatively affecting the productivity of the team/company. It's a performance issue, just complaining about it because it is inappropriate isn't enough. It's important to show it's connection to the contributions in the workplace. That way, you don't appear jealous or nosey.

      Great question Greg, many people often wonder what to do in these situations. How you handle them is very important!

  3. I definitely agree with everyone’s arguments so far. There is no room for inappropriate behavior in the workplace. As J.T said, it may seem harmless at first but there is always the possibility that someone could perceive your actions differently. Not to mention your flirting might make other co-workers feel uncomfortable.

    This summer I worked at a restaurant where two co-workers met and started dating. They made it very obvious that they were together and would sometimes start fights with each other at work. Often they would step outside, during work, and argue. Opposite of Shannon's story, this couple could not keep their relationship and work separate. They were both fired near the end of the summer when management realized this was not a good situation to have in their restaurant.

  4. If only all us men could be as good looking as Tom Brady, be the star quarterback of the New England Patriots (well maybe not anymore…Matt Cassel), date a supermodel, and still get lunch dates in his underwear.

    This artcile reminds me of a summer job I used to have as a camp counselor. Two of the employees were dating and often forgot that thier job invloved being inftont of kids age 6-13 all day. One day their “flirting” went a little too far and one of the campers witnessed them kissing. Now, this may not be a huge deal for the mature population, but infront of a 10 year old, it had quite the affect. The young boy went home and told his mom what he saw at camp that day. His mother immediately called our boss and one of the counselors was fired the next day. Although it may seem harsh, there really is no place for that behavior in that kind of work environment.

    • Kids are so honest – I've got two. And yes, they tell me everything they see at school, a friend's house, etc. So, this doesn't surprise me at all. Thanks for the great example.

  5. I'm currently interning at company where two sets of employee couples recently got married. I immediately thought of them when I read this article. They seem to make it work and keep their relationship very candid. It got me thinking about the opposite of this situation. What if a couple dating in the work place was overtly flirting in the office? It not only poses the threat of a lawsuit for them specifically, but how does it effect others in the office? What if it made co-workers feel uncomfortable and even effected their performances? The impact of flirting in the workplace could go far beyond just the parties involved. Anyone have any experience like this?

    • You make a great point Shannon. I have heard of situations where people feel that those that are 'dating' in the office are getting special treatment or taking advantage of the situation, making others feel uncomfortable. Also, more companies are now making employees sign “love contracts” which says that the company is in no way responsible if things go wrong and they need to fire one or both parties because the relationship is affecting the workplace. So, at least there are work-arounds for those who are in love that can make all parties feel like their bases are covered.

  6. In today's society it is not uncommon for a lawsuit to occur over a sexual harassment case. Stricter company policies and new laws play a big role in the uprise of these cases. I think it is safe to say that almost everyone has witnessed some type of flirting in the workplace one time or another. Although it may look harmless like JT says, I can't imagine it being worth losing a job over and possibly preventing you from getting another one. Why let a stupid remark or action potentially ruin your life. Like the old saying goes, “There is a time and a place for everything.” Your job is not the time or the place to be flirting because it is far too valuable to loose, especially in todays economy.

  7. In today's society it is not uncommon for a lawsuit to occur over a sexual harassment case. Stricter company policies and new laws play a big role in the uprise of these cases. I think it is safe to say that almost everyone has witnessed some type of flirting in the workplace one time or another. Although it may look harmless like JT says, I can't imagine it being worth losing a job over and possibly preventing you from getting another one. Why let a stupid remark or action potentially ruin your life. Like the old saying goes, “There is a time and a place for everything.” Your job is not the time or the place to be flirting because it is far too valuable to loose, especially in todays economy.

    • So true John, everyone has seen some type of flirting in the workplace, and I bet most have even flirted a little too. Let's face it, we're humans – it's inevitable. However, it's the ones that decide to leverage it, or are completely ignorant to the fact that they use it too much, that can get in real trouble. We have become such a 'sue-everyone' country these days. And, thanks to the internet, the things we do are now sent out to everyone. (i.e. Michael Phelps). At least when I was growing up, your past or private life were separate from work, but now it's (unfairly) all fair game. For example, a recruiter told me recently that she hired a young, very pretty woman to join her company. She took the new employee for a tour of the office on her first morning. The company had over 300 employees. By lunch time, the recruiter got an anonymous e-mail with pictures of the new hire doing body-shots on a bar in a very skimpy outfit with a guy. A couple of guys in the office had seen her on the office tour, thought she was hot, looked her up on Facebook and found the pictures on her page and then circulated them around the office. What a way to start your first day of work.

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