I'd say when I was first learning about many of the design patterns, this was my biggest hurdle as well. The examples and analogies were unrelated to real-world scenarios and didn't do much to help me understand the concepts.

It wasn't until I came up with my own real-world examples that were specific to my domain and really applied the design patterns in practice that I really started to understand everything. I don't think it's really the real-world example that helped so much as the actual process it took to arrive at an implementation.