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1
Is the ending happy?
O'Neill was famously irritated that audiences found the ending of the play a happy one. They were seemingly misled by the reunion of Anna and Mat, Mat and Chris's grudging acceptance of each other, and the plan for a little house on land where the new family could be together. O'Neill seeded the end of the play with ominous stage directions and lines in order to suggest that the ending was not happy at all, that at the very least it is ambiguous and at the most it is likely to end in tragedy. Zander Brietzke writes that even without the evocations of the sea's menace and the vagaries of fate, "Chris pulls up the anchor, then, to sail away again, and both he and the proposed bridegroom prepare to leave Anna by herself to run the household. Given this scenario, how will Anna manage to fend for herself? Even as characters propose a new union, they reenact old patterns."
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2
How do the different characters view the sea?
Chris is afraid and suspicious of the sea, mostly because it has drowned and destroyed generations of men in his family and because it is a capricious entity. His fear, though, comes across as superstitious and more of a psychological crutch to explain away the bad things in his life rather than anything rooted in the actual power of nature.
Burke glories in the sea, convinced its raw power is matched by his own raw power as a man. He sees it as something to conquer, as he can conquer Anna.
Anna had previously viewed the sea as the method by which her father betrayed her, but not as a supernatural force. Upon coming to live on the barge after hard years of prostitution, though, Anna comes to look upon it as a healing, cleansing, purifying force.
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3
Is Anna a feminist?
Anna is not a feminist in an overtly political way. She isn't talking about equal pay, voting, reproductive rights, etc. She throws herself at Burke, the exemplar of toxic masculinity. She decides she can live a simple life taking care of him when they marry, and she lets him dictate the process by which all of this will play out—by swearing she is reformed by her love for him. This all sounds pretty damning.
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4
Does any historical context seep into the play, or is it unmoored from its time?
To some extent, the play seems lost in its own little world. The characters don't talk about politics or the economy and we don't see them out in the world. But this is a play where the realities of gender, class, race, and nationality shape a character's upbringing and fortunes, and we are meant to understand that Anna's situation is a result of several different historical forces acting upon her. No, no one mentions President Hoover or even Prohibition, but it's clear that the characters navigate a world structured by external forces.
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5
Should Anna stay with Mat?
This is, of course, subjective, but a careful reader/watcher of this play ought to take pause at the so-called "happy" ending and consider whether or not Anna and Mat are well-suited to each other and if they can achieve marital satisfaction. Both of them are hot-tempered, so bickering is certainly likely. Mat threatened to kill her and called her terrible names, things which are hard to excuse. Mat will be gone often, perhaps leading to resentment in Anna, especially if he has dalliances in the ports and if she is stuck raising children all alone. There may be tensions with Chris. But most likely, Mat will not be able to truly forgive and forget Anna's past, and he may hold it against her. She may have to defend herself constantly, and he may be jealous and suspicious of any man who comes into her orbit. In truth, it sounds like they will have a miserable, acrimonious, tumultuous, and mutually recriminatory relationship.