Dear Lola,

I work in a large office setting where workers typically spend 60-80 hours each week. Due to the long hours, many of us find socializing outside of work to be difficult and we form friendships within the team. I’ve been with this company for about 3 years and have a huge crush on a woman who works with me – not surprising considering the number of hours I spend with her each day. I’ve decided that I would like to ask her out. In the past, other coworkers have dated and it has sometimes turned messy. However, our human resources department has made it clear that it is not against the rules to date, as long as neither person is in a position of power when the relationship starts. I’m in line to get a promotion and I expect it to be announced within the next two months or so. Asking this girl out now is crucial, I won’t get another chance in the future. What do you think I should do?

Maybe Manager 

Advice for humans. They need all the help they can get.

Dear Maybe Manager,

I think you need to take a step back and read the letter you sent me. Then read it again. Keep reading it until you tell me what is wrong. Hint, there is a lot wrong and your list should be a page, at least!

You are not yet ready for the position of management.

Yes, you wrote in for dating advice, and here you are getting job advice. Frankly, you need the job advice first because your stupidity is apparent even to me – a canine who has never worked in an office! You know the rules of the workplace say you cannot date once you’ve been promoted to management, so you decide to start a relationship just prior to it being announced.

You are breaking the spirit of the rule, and you know it.

Managers should be ethical, and seek to lead people to do the right thing. Tip toeing right on the edge of rule breaking is not an attractive trait in any boss, and it will do nothing to earn you the respect of the people on your team. Wouldn’t it be ironic if your almost promotion died on the table because the other managers were put off by your actions? What would your argument to the contrary be? That you aren’t underhanded, you’re just a moron?!

Sure, that will win their trust in your management skills!

That statement was sarcasm. I don’t often feel the need to express that out loud, but it seemed necessary in this case. 

You also aren’t taking into account how your new partner will feel in two months when your promotion is announced. I’m assuming she’ll be told at the same time as everyone else since you cannot play favorites with the employees. She’ll be ‘dating the boss’ and have to put up with all of the snarky comments that people will inevitably whisper about her.

All of her hard work will be diminished in the eyes of her peers.

I’ll just say it since I fear subtlety is not your strong suit. If you actually liked this person, you would not ask her out. You have had enough time to consider doing so, and instead you seem to have only become motivated by a time crunch. How romantic. I’m sure she’ll love being wooed into marriage as you file your taxes and realize how much money you could save if only you were married.

Find a management seminar and take it. Not only will you learn the skills you are currently lacking, you may even find an appropriate person to date!


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39 replies on “Dear Lola – Maybe manager wants to date coworker…

  1. I’m a romantic, so I would have said yes. Life is short, go for it! Sometimes it’s the risk of losing a chance that motivates people to do what they should have done a long time ago. They could let the person know how they feel and explain their concerns re: the office rules and the potential impact and let the other person decide. I do completely see your point though, as it does sound like their motivation isn’t quite as romantic as my rose tinted glasses would hope it is!

    Liked by 1 person

    1. I think most companies now have policy in place to prevent that between boss and worker – mainly due to sexual harassment fears. This guy would be wise to be cautious while he’s still a new boss!


  2. Ouch Lola you are harsh these days!! I was going to say that I would have told him to take a chance and ask her out but I’m afraid you will bite my hand off! Maybe you are right, it probably will alter things at work in the long run and the wise thing to do is just leave the romance now but another part of me can’t help wanting to yell “Go for it, go for it!”. Sorry Lola #globalblogging

    Liked by 1 person

  3. Oh this is a definite no-no in my book. We have a manager at our workplace dating a peer of mine. It’s messy to say the least and there is favouritism for sure! #GlobalBlogging

    Liked by 1 person

    1. Exactly. This situation never works out well. Either the boss loses their career, or the junior loses their position, or the rest of the office hates them because of the favoritism. Even if there is no favoritism, the appearance of favoritism will never go away.


  4. Wow! Lola! You tell him!! So I have a mix bag about this. I actually did date and eventually married someone I worked with. However, neither of us were in management position so that is a completely different ball game. I agree with you that it’s not right to date a subordinate or a potential subordinate. It’s also very unromantic to wait until he feels he’s cornered in order to ask this girl out. If I were the girl I would say no on that principal alone. If she even knows about his potential promotion that is. Which she probably doesn’t and that’s just shady. #GlobalBlogging

    Liked by 1 person

    1. It did not seem like the announcement had been made about his promotion yet, which is why I felt like it was such a bad thing for him to ask her out. He’s jeopardizing her standing in the workplace and she won’t even have known before agreeing to date him. Then she has to decide if she’s just going to be viewed poorly by her coworkers who may feel she started dating him because he confided a promotion or the other option is that she breaks up with the person who is now her boss. He’s just not thinking about anything but what he wants.

      Liked by 1 person

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