I work part-time at a local retailer in my town along with being a full-time student. My boss is the owner of this retailer, and I've worked here since my freshman year... about 4 years now.

There are times where my boss is on the phone with someone or isn't in the office, and I occasionally take those calls... I take messages for him to return the call or resolve the matter in another way. I'm supposed to be taking these calls and I'm supposed to report what has come through for him.

A couple days ago we had a very busy afternoon, and he was on the phone, and in-and-out of the office. Before I was able to even report the phone calls he had missed there were 4. He doesn't really like being on the phone all day long... he knows that, and he knows that I know that. On the way out of telling him he had 4 missed calls, I said light heart-idly, "Have fun!".

Being that I've known him for a while now, and am, I guess, a little closer to him than other employees in the store, is it okay for me to say this in a playful manner? He took it as a joke, and smiled and said, "Oh yeah, I will!" sarcastically. I think it is okay in this instance, but what about when I get a full-time job, especially in a more corporate environment? Is it worth the risk to have a little fun and make light of a situation, or should I be scared of not taking this seriously or possibly making fun of him/his job, etc.?

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    You know your boss better than anyone on this site does, so you have a better idea than any of us whether he would take it in the spirit intended or whether he would feel you were making fun of him. That's true for your current boss, and for future bosses in future jobs. If you don't feel you know your boss well enough to judge, then sure, err on the side of caution. – Carson63000 Oct 17 '13 at 1:41
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    This really isn't an answerable question. You are hoping to get specific insight about an interaction between you and a coworker where the dynamic between you two (as well as both your personalities and what happened on that day) is the only thing which can realistically answer the question. For what it's worth, and it's not much given what I just said, I've said nearly the exact same thing to my manager before as a full time employee in similar "manager about to go do something really tedious/not fun." – enderland Oct 17 '13 at 10:37

To add to Bill's answer:

In this particular situation your "Have fun!" was a recognition that you know that he does not especially like doing those calls, and he knew that you knew that - So he could appreciate that you actually expressed something along the lines of "I know that you don't particulary like this, but at least I wish you some fun/ease/success with it".

Your remark landed well because of that mutual understanding, but notice how much interpretation there is on both sides of the conversation. This is usually the case with 'fun' remarks with a serious undertone (you could name these 'ironic').

It gets even more (socially) complex: your remark also landed well because you interpreted your boss' mood as 'he can receive this without getting mad'. You would not have said this had you seen that he was in a bad mood (for any reason).

So it depends on a lot of things. Knowing the other person well, recognizing the situation ("what's so") helps. But there's no clear prescription when this will work or not.

It also helps if you are prepared to apologize if you misjudge the situation.

Human beings are complex ;-)

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