Ruby on Rails became popular with teenagers partly because of "Why's Poignant Guide to..." (and I forget the exact name.) It was full of funny drawings, jokes, and memes.

Honestly, I couldn't make it past a few panels of this comic. It's a good idea, though.

I think the reason why Why's guide worked is that the content came first, and the jokes were more for comedic relief. Trying to make everything a cutesy analogy doesn't make it more accessible. Pacing is just as important.