Afraid to be Pretty
 

My boss made a comment to me that left me dumb-founded. Does anyone have any insight on what was meant by this? Here's the story:

I work in a small, casual office and I'm way tight with my boss and coworkers. So today as we sat around the lunch table finishing our meals and chatting, the topic of What Not to Wear the TV show came up. My boss (an unusually fashion-conscious, middle-aged male) had never seen the show, but was familiar with the concept - and I told him he should nominate me so I could get the $5,000 shopping spree (and tips!)

He said he'd ham up the letter and say I was a sloppy and careless dresser... and in all honesty, it's not too far from the truth as I work in a veritable construction zone and nice clothes (all clothes, really) get filthy by the end of the work day. I told him that I really can't afford a nice wardrobe to which he responded that he could put one together with a fraction of the $5,000.

Then he looked me in the eye and said, "Your problem is you're afraid to be pretty. You've already got the looks and the figure." I was too stunned to reply, and the normal lunch conversation continued around me.

So my question is: WTF does that mean? Afraid to be pretty? I mean, I'm a confident person and I take great care with my hair and makeup. So my clothes are a little ramshackle at times, but how does that make me afraid to be pretty?

Am I missing something? Ideas anyone?

Well, he answered your question he said you are pretty if only you would dress better ( I hope I didn't hurt your feelings) actually it is a compliment because all you have to do is but on nice clothing and you are the whole package. Where I come from we say you have a Jaguar now all you need to do is wash it. So be flattered

I think he was saying that "you have it, so FLUNT it!" meaning you just need to dress to show off your hard work!

I'd take it as a compliment. He's saying you are pretty and have a great figure. You've got it, so flaunt it.