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I'm a 24 year-old male that has just worked for 3 months in this new job. Sitting next to me a is woman who is 4 years older than I. We have a normal colleague relationship (at least I think it's normal, you know, the usual small talks here and there, going out for a drink together with other co-workers once or twice a month).

She just got her hair cut last weekend and on Monday I jokingly told her, "That new haircut makes your face look bigger." She didn't say anything and I just laughed it away. However, today my manager called me and told me that it may have been quite rude to say that to her (it was only she and I when I commented about her haircut by the way) and it may be considered as harassment. In retrospect, I think he's right. We are not that close yet so I may have overstepped a bit.

I did talk to her directly and apologized but interaction between us still feels awkward. How can I improve this situation?

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    I imagine if you're friends it will just blow over if you apologised and she accepted it and judging by your "We are not that close yet", people have different sense of humours but mocking someone's appearance is generally not a good idea.
    – adamcooney
    Sep 3, 2019 at 8:35
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    @adamcooney Well I learned that that it's not a good idea but how can I fix it? We still have to work together and I don't want this incident to affect our performance.
    – bubiche
    Sep 3, 2019 at 9:07

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Buy her favourite coffee / tea[1], take it to her at her desk and apologize directly and quickly (ideally today, but no later than tomorrow). Don't take right before lunch or hometime.

"Hey listen, I'm really sorry when I said 'hair/face comment'. That was really insensitive of me and I didn't mean to upset you". Resist the urge to add compliments, as they'll probably be taken the wrong way.

[1] For absolute clarity, do not buy flowers / chocolates / expensive gift. She's a colleague, not a date.

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    Agreed. The OP has already apologised but doesn't hurt to do so again. Things will probably still be awkward but then he should allow some time for things to be forgotten.
    – rath
    Sep 3, 2019 at 9:25
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    @rath depending on how the coworker took it the first time it might not be a good idea to bring it up again.
    – jcm
    Sep 3, 2019 at 10:19
  • Thanks, I think the point here is to be sincere about my apology but don't be too cringey or aggressive. I did something similar to what you suggest and I guess time will help make things better.
    – bubiche
    Sep 3, 2019 at 12:35
  • I would just keep it simple and say "Hey, I'm sorry about what I said". Avoid repeating anything that could be embarrassing or offensive.
    – camden_kid
    Sep 3, 2019 at 15:56
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    He already apologized. If the apology was not accepted there is a big chance 2nd attempt is going to make matters even worse. At this point you would be either drawn to constant cycle of guilt and apology or you may end up with another talk to HR about hitting on the colleague.
    – AlexanderM
    Sep 5, 2019 at 14:47
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interaction between us still feels awkward

That's because it IS awkward, she complained to management about what seems to you to be an innocuous remark with no malicious intent.

How can I improve this situation?

There's nothing to be improved. Just a lesson to be learnt and an insight into her personality, don't make any remarks on her appearance. Thinking before you speak at all is actually a major asset in the workplace and perhaps life in general. Friends and colleagues are not the same thing.

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    Am I alone in thinking that making this a management issue is over the top?
    – DrMcCleod
    Sep 3, 2019 at 17:31
  • @DrMcCleod The more I read on this site the more I think I would absolutely hate working in the US. Of course, selection bias plays a role, but man.
    – Minix
    Sep 3, 2019 at 17:37
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    @DrMcCleod maybe, maybe not, it certainly seems so, but you never know what has happened in someones past or personal life that makes them do these sorts of things. Important bit is to learn a lesson from it, analysing with incomplete info isn't constructive, just creates bitterness when there is an easy remedy of just not commenting on her personal appearance.
    – Kilisi ♦
    Sep 3, 2019 at 20:18
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    @DrMcCleod it is an overreaction but it is one somebody people may have and it's one that can negatively affect your career. This is doubly true if the offended colleague has a good reputation with the managers involved, and triply true if you do not.
    – Working Title
    Sep 5, 2019 at 20:23

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