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I'm not very far in the game yet, but do the 5 different endings only depend on your conversation choices? If so, how do you know which is good and bad? They seem cryptic at time
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Yes, only conversation choices puts you on one of the ending paths.

A Double Life - Good ending
Out of the Past - Good ending
Somewhere I'll Find You - Good ending
To Have and Have Not - Bad ending
Petrified Forest - Worst ending

I'm not sure which "Good ending" is the best, but you have three girls to choose.
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JamesBond007: Yes, only conversation choices puts you on one of the ending paths.

A Double Life - Good ending
Out of the Past - Good ending
Somewhere I'll Find You - Good ending
To Have and Have Not - Bad ending
Petrified Forest - Worst ending

I'm not sure which "Good ending" is the best, but you have three girls to choose.
I disagree - Petrified Forest - Hilarious ending :) - this should be canon!

And there are no real 'bad' endings (unless you fail to save the world), at worst there are sad endings :(