this expression, origins in hebrew it comes to explain one's opinion over an action/saying/comment that was taken/said in case that action/saying/comment means something negative or offensive. it's comes the explain the usage of bad language to describe good deeds that were taken by another party.
It means that your acceptable weird. Some people are weird, but it's like dorky weird. People who are weird in a good way are not dorky but they have their own style, they're not scared to be themselves, and they stand out as different in a good way. Overall it's a compliment for the most part.
This past weekend in Chicago I had a 3 way the good way with two exchange students from Sweden.
By Bessy
Oy Vey In A Good Way
"When life gets a little messy but has potential to work out in the end."
Works best when using inflection towards the end of the saying to imply a question.
Nicole "Oh no, the dog just took a shit in my mom's new luggage!" Sam Hey she has already been here two days and leaves in the monrning, That's oy vey in a good way?"