The first day of the BlogHer conference, I had no idea what to do with myself. I know that wardrobe anxiety is common amongst BlogHer attendees every year, but not for me—I was far less concerned with what to wear than what to be.

I would be meeting a gaggle of women who’d never known me before, and I could be anything I wanted! Should I present myself as quirky? Funny? Sophisticated? Easy-going? Suave? Cool? Mysterious?

Little did I know that my stressing out was all in vain, for I really have no control over how I present myself—my overwhelming social awkwardness leaves little room for character development.

Of the top ten most awkward moments of my life, five of them occurred at BlogHer ’10 in New York last week.

Join me, if you will, on a full day of reminiscing how horribly awkward I felt (and really was) at the blogging conference everyone’s been talking about. Every few hours I’ll post another humiliating experience so I can relive my shame in the hopes of getting it out of my system.

I have a whole year to fine-tune my cool.

Yet somehow I don’t think it’ll be long enough.

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Awkward of All Awkwards #5

The first day I arrived in New York, I had arranged to meet up with my internet literary idol, Andrea Boerem (of Harriet’s Pet Pea notoriety). I was stoked. I put together (what I thought was) my most promising outfit:

Here I am taking the subway from the airport to my hotel in said outfit. (By the way, don’t I look ONE HUNDRED YEARS OLD in this picture? My face is literally sagging. I have titled it “Downtrodden.” For obvious reasons.)

Here’s a full shot of the get-up. And jazz hands, for good measure.

I combed my hair. I even brushed my teeth (that is a lie, I did not brush my teeth). I was excited for my chance to meet someone famous and eat a doughnut with her. I wanted to put my best foot forward…to make a good impression.

It’s all I ever want, really.

The only problem was I forgot how much I hate skinny jeans. Well, I don’t hate skinny jeans so much as I hate MY one and only pair of skinny jeans. They are low-rise. And I am a mid-rise kinda girl.

I could go on and on about how much I hate my skinny jeans, but I won’t. Suffice it to say that I thought I was being all New York bohemian chic and trendy, but I did not take into account the fact that I would be hiking up my pants every five steps like a dadgum hillbilly. (Also too I forgot that New York in August is a million degrees humid, and skinny jeans have that awful tendency to schwoop! [sound effects] suck me in just about as tight as any 150 pound tub-a-lub can be sucked in, leaving me trapped, sweltering in a straitjacket of spandex and lycra and denim and death.)

The only way it could’ve been worse is if my clothes had started to fall apart in the middle of my meet-up with the ever-illustrious Andrea Boerem.

Oh wait. They did.

On the subway, not ten minutes after meeting Andrea (on our way to the Doughnut Plant—amazing, for the record), one of the decorative buttons on my blouse just…fell off. Plop. Just like that, it tumbled to the floor of the subway car where I was already feeling foolish, not knowing where to put my hands on the railings and wondering if Andrea could tell I hadn’t brushed my teeth since 2 a.m.

I looked down and cursed that button.

“Really?” I asked the button. “Now? You had to fail me NOW? You made it all the way from Canada to Great Falls at two in the morning, from Great Falls to Minneapolis at nine in the morning, Minneapolis to JFK at two p.m., from JFK to the AirTrain to the E Line to the Hilton at four p.m., AND YOU COULDN’T HAVE HELD UP FOR ANOTHER THIRTY MINUTES TO GET ME THROUGH THIS SOCIAL EMERGENCY? Thanks for nothing, you sorry piece of shit.”

I swooped down to rescue the button from a terrible fate as a street person’s treasure (not that the button deserved my mercy, but I figured I could sew it on later).

I stole a stealthy glance at Andrea to see if she’d noticed my gaffe.

She had.

I tried to laugh it off. “That’s what you get when you spend $2 on a shirt from a thrift store,” I muttered, chuckling nervously like I was on a first date (which I kind of was). I couldn’t have been more awkward about it if I had tugged at my collar with a grimace.

Can you believe that this was the LEAST of my most awkward BlogHer experiences? Just you wait. It gets progressively worse.

Andrea was still lovely though. You should all be her friend. Then again, maybe not, because a recommendation from me probably won’t get you into her good graces. Sorry ’bout that.

I knew I should’ve brushed my teeth.

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Here are the rest of the posts in this series:

Part the Second

Part the Third

Part the Fourth

Part the Fifth

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