The Art Of Awkward

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Making people feel awkward is one of my all time favorite activities. There is no more effective and entertaining way to reveal true character. Alternately, I thoroughly enjoy the squeamish adrenaline of being put to the test of Awkward, myself. Still, there is a fine line between Good Awkward and Bad Awkward. The differences are subtle, so the concept is best demonstrated through examples.

Asking, "So how do you think this date's going so far?" midway through date

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This is one of my favorite things to do on a first date, especially if it’s a total bust. I like to whip the question out at the perfect moment, like right after the guy tells me he forgot his wallet, or asks me what I got on the SATs.

Grandma Unknowingly Purchasing Christmas Gifts From Head Shop

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I couldn’t find a photo of the actual “I’m Fried” t-shirt that my grandma bought all of the girls for Christmas, but you get the idea.

Incidentally, my mom, who’s never touched a drug in her life, also has some wrought-iron cannabis candle holders that she accidentally bought in Venice Beach. She still proudly keeps them on display, citing that she doesn’t think anyone would think that they’re a drug reference.

Trading Cards With Real People On Them

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Receiving Condolence Letter From School After You Faked Your Own Death

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This really happened to MidTownSurprise. See link below:

Doing The Disco Rollem To A Stranger For A Whole Song

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Most will join initially…

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…But only the best will endure.

 

Trying To Explain "Two Girls, One Cup" At A Dinner Party

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Are people seriously still talking about this? If I have to overhear someone explaining the details of this video one more time, I might actually have to watch it.

Disneymoons!...Like A Honeymoon With Fannypacks

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Receiving Hate Mail From Featured SF Sweetheart

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I got an email from an angry Sweetheart the day after I published one of the installments. Somehow, during the 15 minutes she took to fill out the survey, she failed to realize that she didn’t want to fill it out, after all.

Watching A Clockwork Orange With Your Dad

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Probably the most uncomfortable of all uncomfortable moments. But it was art, you know?

ULTIMATELY GOOD AWKWARD

Making Computer Wallpaper Out Of Your Tech Guy's Face

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He thought he was stopping by for a quick tune-up, but really, he was about to discover his new biggest fan.

This Is The Edited Version

…But really, if you like squirming, it’s worth it to sit through the whole thing.

Chris Harrison

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Hosting his way to Badness from day one.

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Discussions

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Hahah I am the queen of awkward, though not always intentionally. My friends swear I love getting myself into the awkwardest of situations. And I think they’re right. If I ever have an office job again I’m SOO doing the tech guy wallpaper thing. Bad awkward, maybe, but sooo funny!

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I watched A Clockwork Orange with my dad too! Haha. Also, I like doing “good awkward” stuff on dates, or just when meeting people: “So, what do you think of me?” “Do you like me or what?” “Oh yeah, my ex-boyfriend always said/did that too.”