What does this mean..?

[WalterWills]

I tried to translate a joke into Japanese..


でも、「面白さ」「どこで笑うか」は、難しいね☆
慣れたら分かるのかな


The first sentence, does it kind of mean, "But, knowing when to laugh is hard"?
I know 面白さ means, "funny-ness", perhaps.

The second sentence: "I wonder if I need to be accustomed (to english humour) to understand?" or "If I was accustomed, I wonder if I'd understand?"



Thanks!