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I'm looking for a word (that may or may not exist) that embodies the feeling of having to choose between two things and knowing that whichever you choose, you will feel like the other was the better choice. Any ideas?

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There is a phrase:

The grass is always greener on the other side of the fence.

This embodies the feeling where one always believes that something else is better rather than their current situation.

This could or could not apply to your situation. It all depends on what it is.

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