Is it normal to joke through a situation and grow from it?

Ugh its frustrating dealing with someone who doesn't like to have serious conversations and jokes around the situation like all zeee time! Ok one of the things my bf likes about me is that I'm funny and have a sense of humor which is true but there are times when I get upset about things and wish he could take me seriously. But gosh I try to be serious and his response is a joke or something like trying to avoid the problem cause he doesn't want to deal w the stress and he can be a little clueless when I'm upset.

So trying to be serious doesn't work. When I go along and joke w him too, he's happier but I feel like we're getting nowhere if I encourage joking more. But I do like to make him laugh and happy and the last thing I would want him to view me as is this girl full of drama who nags. If I confront him bout something, he'll send me like a meme or joke and then I'll do it back but about the subject of the problem. So in a way we're going over the problem but in a funny way. Idk if it works or it makes things worse.

So what do I do when he upsets me? Tell him he upset me and start being serious with him or keep joking around w it and hope he gets he did something wrong and learns his lesson?