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Check50 is inputting a space before the nine, like this: "_9/8/1636" (with the _ in place of a space). Does your code handle that?

From the python doc [strptime usage] Parse a string into a datetime object given a corresponding format text is sent to the function with m/d/Y format That correction should fix the "order"...

Here is some pseudo-code to get you started. It outlines the basic logic, but you have to add the code to implement that logic. while True: date = input('Enter Date: ') if [your test to check ...

You have many problems in your code. You never return anything from parse_date so formatted_date will always be False. You seem to possibly be relying on an implicit return of True but this is an ...

Adding another answer based on your new code. I'm giong to make some changes in that code and point out my changes with comments. NOTE THIS ANSWER ACTUALLY HAS AN ERROR IN IT WHICH I HAVE DELIBERATELY ...

So many problems here. Strongly suggest you break the problem into subproblems. This is the way in programming. Writing one big huge long main function is a nono. It's hard to read, it's hard to ...

This isn't an answer (per se), but shows the output I get when I run check50 against my code. As you can see, it expects a re-prompt, and I get a green smiley.