Do both sentences have the same meaning?
You are into me for 100 dollars.
You owe me 100 dollars.

Question

Do both sentences have the same meaning?
You are into me for 100 dollars.  
You owe me 100 dollars.

Answer

I think they do both mean the same thing.  The first sounds very threatening.  I feel like I would hear it in a gangster movie.

Check out this article:  http://english.stackexchange.com/questions/55410/origin-of-to-be-into-someone-for-a-sum-of-money

Answer

The first sentence doesn't make sense. What meaning are you trying to get across?