To stand with your legs on either side of something, or to be unable to decide between two opposing positions or ideas.
From Middle English stradel, related to 'stride,' combining Old English strœdan (to spread or strew) with the sense of spreading one's legs apart.
Straddling is literally and figuratively about being in the middle—the word describes both the physical awkwardness of sitting between two chairs and the political awkwardness of trying to please both sides of an argument.
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