For me there was also the additional challenge of growing up in an ex-Eastern Bloc country where you could find dodgy pirated copies of games more easily than the real thing.
So you'd end up in a situation where you're trying to beat a bootleg Legend of Kyrandia translated to Russian by looking up walkthroughs in English and somehow trying to match up both without knowing either language very well.
Those were the days.
I surely lost some enjoyment by missing some of the puns at the time, but it's very satisfying being able to play them now, and understand them 100%.
I loved English classes at school, since I could basically NOT study, and still get good marks.
Origin and Lucasarts games were my real teachers :)
And yes, as you've never played Monkey Island: You indeed have to learn the right answers by fighting multiple battles until you're 'trained' enough.
Took me some time to realize I was just supposed to fight through different enemies to gather the right answers and use them on the later battles. And even so I was just trying to match keywords between sentences to realize what was answer to what.
Oh, how much fun one miss playing adventure games not speaking english.*
*(TWPFWP - Third World People, First World Problems).