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Let your freak flag fly

First Example:

Nancy: What are you
wearing for the costume party?
Marco: I’m going to wear
a bear hat, a penguin coat, and cheetah pants. 
I’ll be the weird one of the party.
Nancy: You’re really
going to let your freak flag fly,
Marco: Thanks.  You know me; I’m always trying to be fun.

Meaning: “Let your freak flag fly” is a
positive expression used to show a characteristic that’s hidden or overt
implying a unique or unconventional way of thinking.  Some people feel that the work “freak” might
be a bad thing, but in this instance, it’s a show of approval.

Second Example:

Barbara:  What do you think about my idea for the
holiday party we all wear our clothes inside out?
Tom:  I’m not sure. 
That seems a little crazy.  Don’t
you think?
Barbara:  Oh, come on! 
Let your freak flag fly!  Not
everything has to be formal in life.
Tom:  You know what?  You’re right. 
We should have a little fun in the office every now and again.

Meaning: In this instance, “Let your freak flag fly” is used to show a unique way of thinking,
that although may seem strange, can be a positive thing.  Here Barbara is just trying to create a fun
atmosphere for the day.  It doesn’t necessarily
mean it’s a permanent condition or thought.

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