English is confusing too!

Context is a rich source of confusion in English as well as German.

How about:

“You can’t be too modest” – Do you mean “It is unwise to be too modest, you’ll get trampled underfoot by more ambitious people”? Or do you mean “You should always be as modest as you can’t, don’t overestimate yourself”? Though some constructions of this sort, e.g. “you can’t be too careful” would probably never be misunderstood.

I have a bet on with a friend at the moment. I was thrilled yesterday when he wrote “Look forward to receiving your EUR 20” – until I realised he didn’t mean “You can look forward to receiving …”, it was a casual way of saying “I look forward to receiving…”!