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I haven't felt this relaxed and carefree since I was watch commander at Pearl Harbor.
— Grandpa · The Simpsons
Behind the line May contain spoilers.
Our reading
An editorial interpretation.
The speaker says they feel more relaxed and carefree than at any time since serving as a watch commander at Pearl Harbor. The comparison is darkly comic, since that post is remembered for anything but calm, so the boast of contentment carries an oblivious, ironic sting.
Context reviewed