The Lost Weekend Disappointment

Spoiler alert: Don isn't actually planning to get started on that novel. As we'll learn over the course of this section, he has a tendency to not finish what he starts, and the resulting disappointment drives him <em>mad</em>.

Personal disappointment aside, Don is wracked with guilt over how his actions affect Helen and Wick. To be honest, it's almost worse that they're so sympathetic in spite of everything.

After he returns to find Don missing, Wick's finally fed up. He's done everything he could for his little brother and all he's gotten in return are broken promises and unmet expectations. It might sound harsh, but could you honestly say that you would act differently if you were in Wick's shows?

As we see in this flashback, Don's terminal case of writer's block has been afflicting him for some time. This is also our first real hint that his failure as a writer might be the root of his addiction.

The fact that Don sees his dream of becoming a writer as "silly" shows that he's all but given up. That's a real bummer. Instead of picking up the pieces and moving on with his life, however, he starts falling down a deep, dark hole of depression that just so happens to filled with whiskey. The rest, as they say, is history.

Interestingly, Don feels so dissatisfied about his failed writing career because he was once a real literary hot shot. He's like the star high school athlete who tries and fails to make it in the big leagues. What's more, these early successes gave him such high expectations for the future that they could never hope to be met.

As you can imagine, this chain of half-baked and unfinished novels leads us all the way to the present day and The Bottle. It's also worth noting that Don rushed to New York City immediately after dropping out of college, which is a classic example of "too much, too soon" if we've ever see one.

That "guy," btw, is Don's alcoholism. This quote confirms something that we had already suspected—that Don turned to booze after his first, failed attempts at writing novels. This leads to a nasty Catch-22 in which he drinks to write, but ends up drinking so much that he can't.

In other words, Don couldn't live with himself knowing that he completely failed to achieve his dreams. It would be too great a disappointment. Still, we'd argue that he's failing to achieve his dream even without the "nice job," so it shouldn't make that much of a difference, right?

In many ways, Wick's generosity only makes Don feel more like a disappointment. After all, he's a thirty-something who still gets an allowance from his older bro—there's no way to frame that so it doesn't seem lame. Once again, we see Don's little vicious cycle back in action.