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Manipulation
[While Wick is looking for a typewriter, at Don's behest, Don tries to untie a bottle he had hidden by hanging it from a rope outside of his window]
The opening scene, in which Don struggles to free a bottle he's hung out of the window, perfectly sets the tone for the film. While Don's machinations can be amusing at times, they reveal a deeply conflicted and often manipulative man, so desperate for a fix that he'll do anything to get it.
DON: If we took the later train, then Helen wouldn't have to go by herself. She's got two tickets, hasn't she?
See what we mean? We're hardly ten minutes into the movie and Don is already scheming and manipulating likes he's playing Monopoly. Give it a rest, buddy—you're only making yourself look like a jerk.
DON: Alright, if you don't believe me, take my keys and lock me in like a dog!
HELEN: We've got to trust Don, that's the only way.
Don frequently manipulates Wick and Helen by playing off their guilt. This is a great example of that: Don acts offended by the suggestion that he wants to have a drink in order to—well—have a drink. This sort of emotional manipulation is especially dark given that it's done to the people who love him most.
[Don is holding the cleaning lady's ten dollar payment in his hand.]
DON: Sorry, Mrs. Boyle, it isn't there. He must have forgotten.
As the movie continues, Don's manipulations grow increasingly egregious. Hiding a bottle of whiskey from your brother is one thing, but stealing a cleaning lady's paycheck is a whole different can of worms.
DON: I'll roll one bottle in a copy of the <em>Saturday Evening Post</em> so my brother can discover it like that. I want him to discover it to set his mind at ease.
Don's alcohol-smuggling plans are so complex that he should get hired by the C.I.A. or something. On the other hand, this also show how desperate Don has become, buying an extra bottle of whiskey simply to ensure that he'll have one during the weekend. It's pretty sad when you think about it.
[Don drops a bottle of whiskey.]
HELEN: Who threw that?
DON: It fell out of my pocket.
HELEN: Do you always carry those things?
DON: Well, no, you see, that friend of mine uptown, he has a slight cold.
As we see in this flashback, Don has been lying and manipulating from day one of his relationship with Helen. Heck, he starts fibbing within the first fifteen minutes. That's got to be a record. We hate to pile on, but that's not exactly the best way to kick off a relationship.
[Don steals a woman's purse while she cuddles with her lover.]
Eventually, Don gets so desperate that he resorts to thievery. It's not his most charming moment. What's more, it shows that Don's impressive manipulation skills are turning up diminishing returns, and that's really bad for him.
DON: Could you let me have some money?
GLORIA: Say, you out of your mind? Don't be ridic. [...]
[Don kisses her.]
[...]
GLORIA: How much money?
This is a low point, even for Don. It's not just that he already has a girlfriend, though that would be bad enough. More than that, it's that he so flagrantly takes advantage of Gloria and her attraction to him with zero concern for how it affects her. That girl is going to have some serious trust issues when everything is said and done.
SHOPKEEPER: That'll be $2.15.
DON: Come on, I need that liquor. I want it and I'm going to get it, understand? I'm going to walk out of here with that quarter of rye, one way or another.
While Don's decision to steal that lady's purse was pretty bad, it was still very much in line with the guy that Don is. It's small stakes stuff. This, on the other hand, is something completely different. If anything, it shows just how dark and violent Don is becoming, and how that darkness now threatens to consume him whole.
HELEN: I knew there was a core of something. Well, there is a core, and now I know was it is—a sponge. And to soak it full you'll do anything that's ruthless, selfish, dishonest.
Although Helen makes up with Don after this fight (and after he quits booze), she's not saying anything that isn't true. After all, we've seen Don do plenty of ruthless, selfish, and dishonest things. We've seen him manipulate people without an ounce of empathy. It wasn't cute. Hopefully, those habits will fall to the wayside as soon as the whiskey does.
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