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.?