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It's unfair to imply that a guy asking in a situation where the answer may be a no is creepy. It's unfair to imply that a guy can always know. This is just plain unfair, and silly. But if you ask someone out in the workplace and she says no that gets super uncomfortable for everyone.
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The ugly, unfair truth about looking beautiful

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Ask Polly: My Boyfriend Thinks I'm Ugly - The Awl

It took me years to realize that despite being born with a rare facial disfigurement, beauty is more than a cold calculation. I am ugly. Or so I was told by the boy that sat behind me in my seventh grade art class. Even the teacher thinks so. Two years earlier, a different boy, whose name I can no longer remember, angrily asked me what was wrong with my face, after I beat him in a game of handball during recess.
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Ask Polly: My Boyfriend Thinks I'm Ugly

When he first met me, he had fallen for me straight away, always coming in for coffee on my shift at the local cafe, always texting first, offering rides home, asking me out first. He was very sweet and persistent. He never complimented me on any of my physical traits, yet every weekend we hung out, he would somehow manage to tell me that he wanted me to have larger breasts like so-and-so, get more toned legs like this person, grow your hair long and put on some eye shadow….
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Last month, after an early screening, Jeffrey Wells at Hollwyood Elsewhere revealed that the idea of "marginally unattractive guys -- witty stoners, clever fatties, doughy-bodied dorks, thoughtful-sensitive dweebs and bearish oversize guys in their 20s and 30s" playing "romantic leads" just doesn't wash with him " Eclipse of the Hunk? God forbid. Upon seeing Segel's upper torso at the beginning of "Forgetting Sarah Marshall" this is before all the rest of him is bared to the world in a painfully funny break-up scene , Wells says:.
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