It originally means, Really, Okay, before people used it. At times when they don't have the correct words or sentences to say what's on their mind.
Oh, Well if the kid wants Heineken, he got to be 21 years old. Alright?
'oh, well' is an interjection that means 'i could not care less.'
i spent my girlfriend's birthday money at the strip club. oh, well. she's maxed out my texaco card!