Isn't that the strangest expression?
And the emphasis people put on the words..
"Well, she can't win for LOSIN', CAN she?"
As if losing should somehow cause one to be more prone to winning.
I heard someone use this expression today at work, and it me with special clarity. Clarity as to what a nonsense thing that is to say. And then i thought that it must have some meaning, some story behind it. So when i got home, i looked up the phrase at www.phrases.org.uk. I picked this site because it was the first one on the list when i googled "can't win for losin' phrase origin," and because some part of me believes that brits know more about English than i do.
I thought i was going to find some hidden meaning or story in the meaning of this phrase, but instead i learned that the phrase intends to indicate that one cannot win because of having done too much losing. Not enlightening.
Urban Dictionary, on the exactly same hand, explains that "things would be going great for you if they weren't going so badly."
In a last ditch effort, i explored wikipedia for an explanation with any level of profundity. (is that really a word?)
And i found something with a little depth: The indication that you're losing so badly that even if you were in a contest for who could lose the most, you couldn't even win that.
Makes me think a little of George Costanza.
Now THERE's a fella who can't win for losing.
All in all, however, it's a phrase i've decided not to use. It has no profitable meaning. And the meaning it does have just isn't very nice. I mean, is it? I know it wouldn't feel good to have anyone say that about me. :(
Believe it or not, there's sort of a Biblical view on this little rambling interjection into the oddities of the English language, 'cause i was listening to Matthew today, and in Matthew 12:36, Jesus says that man will have to give an account for every idle word. Wow! I don't think we can really imagine that. Thankfully, in the Bible, there's also an awful lot of talk about repentance and forgiveness and remission of sins. But it seems prudent to cut down on the idle words as much as i can. And think of some non-idle words to replace them with. Like "Can't Lose for Winning!" That's how i feel about life in God's hands. Even when things look bleak on the outside. I'm winning too much on the spiritual side to ever feel like i'm losing anything.