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The Titanic
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I know Communi-Fan is trying to be diplomatic but I strongly disagree with the idea that Jeff's issues with Annie are somehow minor in comparison to his other problems. His feelings for Annie is something he has struggled with for years and unlike those other things it's not really as resolved. For instance, Jeff

Agree. It's why they are critics and not TV show writers.

"Jeff has clearly come a long way, but he could have really demonstrated his growth by telling Annie to save her kisses until Troy gets back from his trip."

Have to disagree about the kiss blunting Jeff's maturation arc. This is exactly how the arc where a selfish guy learning to love should end. He admits he wants her but understands he needs to let her go. I don't know what would be the point of him telling Annie to go kiss Troy since she doesn't need closure from him.