Charlie: In one night he did what we couldn't do in a lifetime Alan: He broke her Charlie: Chewed her up and spit her out Alan: It was a beautiful thing.
Jake was spoiled and overprotected by the mother. This produces a clueless teenager. To become a smart teenager, you have to be put in tough situations .
Jake asking Alan "what did I ever do to you?" is a question he should ask to the writers because he was so funny as a kid and then they turned him into a boring and dumb bag of rocks.
It would have been much smarter for Alan to give Jake the best day of his life AFTER visiting Evelyn. Give a kid a great day and end it with bad news is crushing.