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For me it's completely the opposite experience....
Years and years and I'm still worried about going outside. Tonight was a good example. Time for my weekly "drive of fright" to the mailbox around the block.
Lots of years of practice. I live alone so I can do what I want. I put the "going out" effort into everything, and it all seems to look good in the mirror. I step to the door, the houses on the street are all dark. But just as before I step out I get the second thoughts. Its dark out, and I know no one would think to look twice at the size 10 brunette walking to the car, but I think "what if a neighbor is just looking out now...they know that's my car and...."
Get undressed, clean up and back to the couch and Netflix. Maybe I'll try Thursday.
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Doing makeup is just a part of going out.
As long as I look trim taut and terrific when I go out the door I feel I have achieved the look.
I do have other feelings that well up inside me from time to time and do dress accordingly.