Dating Your Boss


Happy Valentine’s Day to all. Given that today is that special day for all couples and this is a site about careers, I thought what better to write about than dating on the job? Just as I was going to write, I found a site that has already covered this topic thoroughly. I have included the article here:

Q: Dear April,
I think I’m in love with my boss! He’s not married, and he’s not too old for me, but somehow, I feel like I’m doing something wrong. Am I? Signed, Working It

A: Dear Working It:

Of course you fell in love with your boss. You’re probably like every other workingwoman who is dedicated and hard working, so much so that her commitment to work makes it impossible to meet anyone outside of work. You’re probably not just a nine to five worker, you’re that successful someone who works extra hours, weekends, and is trying to get ahead and do well. You know what that makes you? Sexy!

Men love women who are confident and focused with interests and areas of expertise. Who wouldn’t? Think about it. It goes both ways. Women love men who are like that, too, and what simpler place to meet them than at work?

However, that doesn’t mean you have to go through with it. The easiest way to get out of dating someone at work is to simply explain, Sorry. I don’t date people I work with. Then hope one of you gets fired.

Here are some considerations in deciding if dating someone at work is right for you:

Pros and Cons of Dating A Co-Worker


1. You know he or she has a job. You know how he or she is thought of at work.

2. You have a lot in common and can be more productive because you have this in common.

3. There is an understanding of each other’s work schedules. One of you isn’t angry if the other has to work late because you have a better understanding of what’s involved.


1. If you break up or have a fight, you don’t get the respite and space you may need to heal or cool down because you’ll see the person so often at work.

2. Sexual harassment is a real problem that can occur more easily when there are lines that get blurred at work. In addition, people gossip and you may make enemies if one of you is higher up in the corporate or business ladder at work, and the one is lower down may be perceived as getting unfair advantages.

3. If one of you wants a break from work and the other is into work, you may not have an escape from it — even out of the office.

Date at Work, But Work at Dating
Okay, so you’ve thought about it, and you’re still with me that dating someone from work is viable and can even be successful.

Even though it’s often advised against, dating people you work with makes practical sense after all, we spend so much of our lives in the office, there’s often no other way or time to meet anyone else. But that’s not to say you don’t have to be smart extra smart, in fact about your choices, and take special precautions if you’re going to venture into an office romance.

Water Cooler Gossip
The one overriding warning worth heeding the one that should dictate all of your actions and words is this: People talk. No matter how friendly your co-workers are, or how tight-lipped the object of your affection seems, secrets are almost always spilled, one way or another, whether accidentally or intentionally. Translation? Say nothing and do nothing that you do not want everyone else to know about. This means no chit-chat with the girls at the water cooler about his size or performance, and no pillow talk with him about how much you loathe your boss, and can’t wait to take over his or her job. There’s too much at stake like, your livelihood to take risks, and there’s too much to lose like a potentially great love not to give it a shot.

Rules About Dating Co-Workers
1. Don’t mix business and pleasure on company time. Agree to date out of work hours, but don’t turn a business lunch into a romantic lunch.

2. Stay fair. Don’t give someone you’re dating better work or pay, and don’t punish someone you’re breaking up with by giving him or her worse work or pay. Otherwise, you may find yourself on the receiving end of a lawsuit!

3. Make sure he or she is actually single. If they’re not, then keep personal remarks at work limited to sports, the weather and the kids. Don’t gripe or listen to gripes about a spouse. I’m sorry, I’m not comfortable talking about your wife. I want to keep our relationship all business because I value us as co-workers, is all you need to say and do.

Dating Your Boss
Dating your boss may be a lightning rod for trouble, but the truth is it’s natural to fall in love with someone you work with, that you admire. And if you’re a terrific asset to the company, you’re going to catch your boss’s attention with your work. If you’re attractive, and there’s chemistry between the two of you, it’s natural for a relationship to become possible. Therefore, dating the boss is something that is taboo only if you let it be. That said, there are definitely ‘Do’s & Don’ts’ to follow that will make or break your romance.

Do’s and Don’ts For Dating Your Boss
1. Don’t Boast. Your boss may look like Brad Pitt or Angelina Jolie, and you may be so pumped up that you’ve got a hot date with hottie — but keep your feelings to yourself — and your friends outside of work. This is a great time to start practicing certain boundaries. Work gossip is inevitable. Practice good behavior by keeping the water cooler talk to work and the weather.

2. Don’t Make Out or Have Sex At Work. Sorry to burst your bubble if you’ve got fantasies of locking the board room door and doing it on the conference table while the staff waits impatiently for the janitor to jimmy the lock open. Keep all sex and affection outside of office parameters. It’s okay to meet at the office, but don’t smooch at the office.

3. Don’t Have Love Spats At Work. If the sex wasn’t great the night before, don’t bring your disappointment to your staff meetings — no pun intended. You will have to practice wearing two hats — even if you’re mad at the boss you’re dating, don’t put the kabosh on his comments at the Monday morning meeting and act out your frustrations at work.

4. Do Put Rumors To Rest. If you hear gossip, don’t fuel the fire by denying the truth. Everyone finds out that you’re dating eventually. While you should not announce your relationship, you can say, “Yes, we’re dating. We’re both single adults and we were lucky enough to have found each other! We’re working very hard to keep our social life separate from our work life.” And smile.

5. Do Communicate Well. Dating your boss seriously, is a lot like blending families because there are so many people involved — whether you like it or not — and they’re all wondering how your relationship is going to affect them. Put yourself in your co-workers shoes, and talk openly and often with your honey about what you see, feel and want to do about it.

Remember that both dating and working are natural parts of life, and it’s completely natural to become attracted to people you work with. If you’re both single and available, go for it! But be impeccable with your behavior and your work. You’re going to be under more scrutiny in this relationship than you would be if you were dating someone you didn’t work with.

Although I am sure we have all been attracted to co-workers and bosses there are certainly some issues we must be aware of. Does anyone have good dating stories to share?

9 thoughts on “Dating Your Boss

  1. This reminds me of a relationship I had with a co-worker that did the exact opposite of the above advice.. haha. Although it was not “politically correct” at all, it was one hell of an exciting time! I do however agree with all these tips. Do your best to follow the advice above. I wish I had

    1. Hey Jeff,
      What were you thinking becoming an independent consultant?? You’ve eliminated yourself from the “co-worker dating pool”!
      John A.

    1. I know what the hell was wrong with me?
      But then I meet enough people through business, and they’re not really co-workers so in some ways it opens new opportunities….
      Too bad you live in California, Jane.
      Your loss, I’m always told I have a great ass…
      (Comments wont nest below this level)

  2. I wish I had co-workers to date! hahaha . . . great blog! Found you through John Chow’s Giving Some Love Post!

  3. I don’t think it’s a good idea ever to date someone at work. One of you is destined to be hurt emotionally and perhaps financially.

  4. I’m “dating” my boss– we are totally in love with one another, but because it isn’t “appropriate” it is being kept a secret. So, we never go out anywhere together outside of close friend’s homes…but the rumor mill has started anyway- and the denials have been made–so now we are totally stuck. We’ve talked about one of us leaving, giving it some time, and then pretending it just started. But its a good place to work, we’ve both been there a while, and there aren’t too many options locally. So I’m currently debating taking the plunge and getting a new job, or just doing my boss on the conference room table and checking that off my list of fantasies!

  5. My boss and I are both attracted towards each other. I acted out first disclosing my feelings for him. We both are married and no way we can have life together.e wnt me to quit if he wants us to get together, but i dont like mixing work and personal life..thats wer our relationshiphas halted and waiting for some change in direction.
    With retrospection I fel it was easier f I would have denied it and not been open about it. Coz now he does not respect me in many ways. I hate hm for doing that to me…so before you wana express your honest feeling get to know them…..

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