This Week in Awkward: 10/17


You may have seen the splash Kirstie and Amy made on their Huff Post Live interviews this week (if not, click on their names and go see them rock it!), but don’t despair, we’re still the most awkward kids on the block. Need proof? Boobs made us famous. Our top searches this week are “boob darling” —it’s like a whole site-wide awkward. So to be supportive, our writers pulled out their extra awkward stories in solidarity. Aren’t they just darling?

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ELLA: “Future Cat Lady in Training”

So there’s this guy I have had the biggest crush on, and assumed was completely unattainable. He came to me for advice when his girlfriend broke up with him. Afterwards, he told me how he’s comfortable talking to me about all of this and how he “likes” me. Of course, my social skills are forever stuck in middle school and I instinctively did a double-take when he said that. So what did I do? I casually asked him to repeat himself. After he did, I replied with a classic awkward pause followed by a nonchalant response: “I like your company… I also like cats.”


KATE: “ARG-You Going to Compliment My Outfit?”

I work at a student-run coffee shop on my college campus, and in order to follow health code without resorting to hairnets, we have a collection of strange hats behind the counter. I’ve been wearing the pirate hat (which is pretty much exactly what you think it is) every shift for the last year, and it’s resulted in some pretty awkward moments, including the time I accidentally left work while still wearing the pirate hat, and walked halfway across campus before realizing that I was still wearing the pirate hat. But this week takes the cake. I had gotten up at 6am for work and put on an outfit I was pretty proud of, which involved lightwash denim, a bright yellow sweater, and a black-and-white striped dress. While I was manning the register, my head festooned with my pirate hat, an older woman came up to order and said, in this totally genuine and kind voice, “Oh, so you’re dressing up for Halloween a bit early, then?” My response: “Well, I have to wear this hat for work…and this is just my outfit.”


KATIE: “A Bad Game of Telephone”

I was on a conference call, a very long one at that, and I thought I was on mute. (You probably know where this is going). I’d been amidst this absurdly ridiculous project at work and needed to update my coworker about it. So I loudly say “We’re probably going to have to email them to just resend it to us since they inevitably lost it.” in a really sarcastic tone of voice. All the sudden all the voices in my ear were silenced and there’s cricket noises over the phone. To make matters worse, some of the “them” I was referring to were on the call.

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HALEY: “Hurt the Ones Who Help”

It was raining and I’m traipsing through the downpour on my way to another building on the college campus at which I work. All the old academic buildings have slick tile floors, and I had on rubber rainboots. Well, Haley took a tumble. As I was closing up my umbrella, both my feet came right out from under me and I landed on my back in a dirty puddle on the floor. A nice guy comes over to help me get up, and as I’m righting myself, I slip and fall again. And my umbrella opened and hit the guy in the stomach. He just left me there. It was pathetic.

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So how awkward was your week on a scale of getting the alert at 11:30 at night that you’re due back to work in the government the next day while you’re vacationing in Bosnia and the Miley/Mumford mashup being better than the real “Wrecking Ball” video? Tweet us @litdarling

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