Dating Your Boss

A reader writes…

I have a major crush on my supervisor, and it’s making work awkward. What are your thoughts about dating the boss?


Dear, “Smitten Kitten,”

So… you report to a looker, eh? Well one thing’s for sure…  I bet it makes going to work a giddy experience (not to mention the fact that you’re probably dressed to the nines each day!)

As much as a “crush” can seem innocent, or you may want to DATE this person, I highly advise against it.  Things can evolve into a big mess – from sexual harassment to office gossip… it’s just a big no-no.
While employed, you need to keep your relationship strictly professional.  No flirting or hanky-panky – it could seriously jeopardize your job and damage your reputation.  Get out there and find someone similar (away from the office) – but when it comes to your boss, consider him (or her) off limits!

Hey readers, has anyone been in a similar situation?  What did YOU do?

I’d also love to hear from the managers / supervisors out there – What’s your take on this situation?

16 Comments (+add yours?)

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    May 19, 2014 @ 19:41:22

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  2. Crush on my best friend
    Apr 06, 2012 @ 23:32:12

    Woah this blog is great i like studying your posts. Keep up the great work! You already know, many persons are looking round for this information, you can aid them greatly.


  3. judy
    Jan 10, 2012 @ 00:28:19

    I have been seeing my GM for almost a year now. We have managed to keep things under wraps up to this point. He doesn’t treat me any differently than my co-workers, and we both remain very professional. Generally, our work environment is very laid back so it’s not difficult at all. We steal little moments from time to time. At first I was hesitant to begin anything because of the fact. Since day one though, I felt like we had this inexplicable connection between us, we understood each other, no problem.


  4. Joe
    Sep 19, 2011 @ 11:46:22

    I do believe Travis Tritt wrote and sang a song about this and it was called


  5. John Jensen
    Sep 12, 2011 @ 10:17:19

    At my last job there were several people who became enamored w/ each other. Some were out and out obvious with it and others were sneaky. Those who were transparent about it seemed to keep their jobs, while those who tried to keep it a secret had other problems and were let go. I’m not endorsing this but If I were a super/manager I’d want to know up front who’s doing what in my dept. so I could be prepared for the worst or the best. You and your would be partner are not the only persons being affected here…


    • m.capriola
      Jan 11, 2012 @ 10:47:17

      Something similar happened in the resort where I worked. Male concierge was dating a woman in Sales secretely until his wife found out and made him quit his job.
      The woman in Sales was fired later on for other reasons that were just as sneaky.

      Other couples who dated openly and were in different departments did not have any problems (except for the Head Concierge who decided to resign her job after the GM she was dating moved on to another location).

      So, yes, Mr Jensen is correct: the sneaky people tend to get found out and lose their jobs.


  6. m. Capriola
    Sep 12, 2011 @ 06:17:24

    Last outfit I worked for had a few cases in which one of the supervisors was dating the General Manager. Anything she wanted, she got. Other supevisors and managers had to deal with the fact that she unofficially outranked them all.

    Until the GM took a job somewhere else and didn’t bring her with him. Then she had to look for a new job because the new GM reorganized and took away a lot of responsibilities he felt she didn’t need. And I wonder how many of her colleagues suggested to the new boss that she had too much on her plate.

    In summary, Don’t date the boss. For one thing, everyone else in your department will resent you.


  7. 1844white
    Sep 06, 2011 @ 20:19:08

    i had a crush since the first time i saw him , what could i do? and i knew he liked me too, so i went to him and talk about my feelings , he said it could be because he was the boss and it wouldnt be professional but we are human and human have feelings , so i left the company and we still are in a wonderfull relationship that lasts years now …


  8. MJ
    Sep 06, 2011 @ 13:44:41

    I’m a HR professional and I strongly encourage you to find another position or job if you must be with this person. You can’t help who you fall for but you could put your job and his at risk. It’s not worth the ramifications if others find out. Most importanly, do your homework as Michele Vics warned because it may all be in vain.


  9. Jill
    Sep 06, 2011 @ 13:41:37

    Might have been a bad idea to start, but it turned out for me. We’ve been married 22 years this Fall. Best thing I ever did. We kept it quiet, until we decided to get married, at which point I requested a transfer. I continued to work for the company, but in a different location.


  10. roni
    Sep 06, 2011 @ 12:49:48

    I say…get to know the boss really well. They may like you too. It could be a wedding in the future. I say don’t reveal your crush for a long time perhaps years. It may just be a phase. Letting co-worers know can cause the situation to become more awkward for you and your boss. Keep your relationship professional and let them make the first move, if ever. Just know it may always be a crush that you could never act on.


  11. Michele Vics
    Sep 06, 2011 @ 11:52:16

    Bad karma!!! I made this mistake before when I had my job at a bank processing center. My crush was so profound, it could all too easily be mistaken for true love. The biggest mistake was not finding out right off the bat if he was married, which happened to be the case. I begrudgingly accepted it, tho’ he admitted his relationship was on the skids. As much as I tried to consider him a friend, part of me felt devastated when I found out he got sacked a few months later. It was actually a grievous blessing.


  12. A.J. Boyle
    Sep 06, 2011 @ 09:06:41

    Dating your boss is an exceptionally bad idea. Do your looking for romance somewhere else than the place where you work and you’ll enjoy both longer and less stressful employment as well as a less stressful love life.


  13. Indy
    Sep 06, 2011 @ 08:34:22

    I would also advice not to date your supervisor nor your clients…that can be real messy and sadly there are too many places where this is happening and no one do anythinga bout it. Worst yet, the supervisor may even encourage it.


  14. Christa Huffine
    Sep 06, 2011 @ 08:29:45

    I actually accepted a date with one of my supervisors. He wasn’t my immediate supervisors. Thing is that I worked in a call center, and he was one of the guys who handled ‘ground control’. Usually he would give me a break off the phone and have me watch the call board.

    Later I found out that he was notorious for making his way through the agents. I finally fessed up to my immediate supervisor (who gave me a lecture). He called me back to the booth one last time, which made my supervisor nearly fall off her seat when she got the call. I handled the situation professionally, but I filed to be moved to third shift. I was planning on doing it anyway for school. He then moved to third shift, and I told my new supervisor.

    I later left the company, but it had nothing to do with that guy. I just needed to finish school. Would I do it all over again, if I had another chance? GOD, no.


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Anita Clew's blog posts are intended for general guidance and should never be taken as legal advice. In all instances where harassment, inequity, or unfair treatment is believed to be present, please consult your HR Department or legal representation.
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