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1.
1) to turn both sideways and backwards
2) To turn sideways except cooler
"I just turned my head sidewards and it was rightside up"
by zexsudel October 20, 2004
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2.
Unexpected change in direction of progression in life or any other activity.
Going off the rails.
Can be positive or negative.
Person A: "Did you hear about whats-her-face? She's working for McDonalds now instead of her Government job."
Person B: "Sounds like she's going sidewards."

"Her life is sidewards now that she's won lotto"
by FounderEffect April 08, 2012
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