Dear “Awkward Moment of the Year” Award Committee

Dear “Awkward Moment of the Year” Award Committee,
Hi, how’s it going?
I’m not really sure how the whole democratic process of voting for this award goes, but personally, I’d like to nominate, well, most of last night, but particularly one moment.
But first, it’s important to know a little something about me.
See, I’m a child of divorce. I know, it’s hard… plus, it’s weird to call myself a “child of divorce” when it happened when I was 19 or 20. I know, it’s hard being me, Judy Blume’s working on a book about how much it sucks to be me.
Without getting too deep into it, my parent’s split was… less than amicable, with my mother leaving my father for a man that she had been with while my parents were still married. Scandal, right?
No, scandal is when your mother calls her new husband the name of her ex-husband, the man she left to be with her “partner in crime.” Yeah, they don’t make greeting cards for that shit…
Look, I’m not expecting to win the damn award, it’d just be nice to place this year, ya know?
Sincerely,
Calhoun

Dear Date (Pt. 2)

Dear Date,
Hi again. Let me start off by saying, I had a great time last night. It was nice to just get together and talk with someone… cuz, ya know, I just don’t do enough talking or whatever. Yeah, nobody believed that. I pretty much never shut up.
Lemme start over.
Hi, I had a lotta fun last night. But this is about the end of the evening… as is customary, the first date ended with a kiss, but I wanted to defend myself there. See, I swear I’m a better kisser than that.
I wasn’t sure if we were doing, like, a full-on kiss, if there was gonna be tongue or how long it was gonna be or anything like that.
Plus, the bouncer from the strip club across the street wasn’t helping matters… anyways, I just wanted to say, if I could get a do-over? Yeah, that’d be great.
I mean, I know we’re already going to a movie on Saturday so hopefully I didn’t fuck up that badly, but I just kinda wanted to defend my honor or whatever. I mean, I am a good kisser. Everybody says so.
Okay, not “everybody.” I mean, I’m not some sort of kissing slut or something.
Ya know what? I really don’t see myself winning this one, so I’ll leave it with “see you Saturday.”
Until then…
Sincerely,
Calhoun

Dear Professor

Dear Professor,
I think I have some explaining to do.
When I came in to your office the other day, I brought along my comic book backpack as usual.
Now, this wouldn’t be a big deal if I didn’t feel like I already looked like a pedophile with my beard and all.
Still, I decided to ignore the obvious jokes and proceed with business as usual.
It was only when I opened my backpack, which had held a loosely-capped bottle of whiskey the night before, that I realized the problem.
Let’s put it all together, shall we?
Kid’s backpack + whiskey + vaguely pedophile beard = awkward situation.
Now, I swear I’m not a pedophile, but I also recognize how things look.
Anyways, I just wanted to apologize… that whiskey smell can kinda linger and your office isn’t too big to begin with.
So for the myriad of misunderstandings yesterday, I am truly sorry.
Sincerely,
Calhoun

Dear UPS Guy

Dear UPS Guy,
I don’t normally answer the door like that.
Seriously, I don’t.
But here’s the thing. It’s, like, crazy hot in my apartment right now, made worse by the 55 lbs. dog that opts to sleep on my chest.
The only way it’s bearable is when I wear… well, let’s just say less is more.
Besides, I’ve totally seen dudes wearing gym shorts that are shorter than my boxer briefs, so don’t even act all traumatized, okay?
However, in hindsight, asking “do you have a package for me?” was a poor choice of words… sorry.
Sincerely,
Calhoun

Dear Guy Making Awkward Eye Contact

Dear Guy Making Awkward Eye Contact,
Yes, it’s me. And by “me” I mean, we’ve seen each other outside of the confines of this coffee shop. In fact, I think there’s a good possibility that we live on the same street.
… but that’s not why you’re looking at me weird, is it?
Yes, it’s also the same “me” that you saw walking his dog at 6:30 on a Sunday morning… in his boxer briefs.
Can I just explain myself though? Okay, the dog really needed to go out and it was early in the morning so I was tired, but I also thought “who else is crazy enough to be up and about at this ungodly hour?”
Wow… that didn’t really take long to explain… nor do I think it made a good case for my sanity.
Ya know what? I can see that this is doing very little to persuade you that I’m not some sort of sexual deviant, so I’m just gonna quit while I’m ahead.
Sincerely,
Calhoun

Dear Uncomfortably Aggressively Flirtatious Guy

I actually would've preferred this

Dear Uncomfortably Aggressively Flirtatious Guy,
A compliment is one thing… in fact, you can tell by the fact that I said “thanks, man” and turned away from you. Truth of the matter is I don’t even much care for compliments, but still, it comes from a good place, so why the hell not?
Asking me to sit by you? Okay, now we’re getting into some weirder territory… That’d probably explain why I shyly smiled and went about ordering my drink from the register. The fact that I did not, in fact, sit by you should indicate some lack of interest on my part. I should’ve probably verbalized it by now, but hindsight is 20/20 sorta thing.
No, but I think it was when I clearly didn’t return to sit next to you, but you came and sat next to me, despite me clearly stating that I was trying to get work done and even wearing my headphones to block out your inane prattling. I don’t think there are enough words in the English language for how uncomfortable I was at this point.
But oh wait, it actually gets worse. The rousing and staggeringly one-sided conversation you had about auras and numerology was finally the breaking point. Not only did I spend most of that conversation just thinking to myself “wow, this is the most ridiculous thing I’ve ever heard” but about halfway through, I couldn’t help but notice you had something stuck in your teeth. While you continued to talk for 20 more minutes, trying to hold my hand a couple of times in there, I could not stop staring at whatever that was…
Was it a poppyseed? Does Caribou even sell anything with poppyseeds?
Needless to say, these questions were far more interesting than anything you had to say, so please forgive me that I had to make an excuse to leave, but rest assured, you probably wouldn’t have stopped talk anytime soon and, well, no matter how long you talked, the conversation really wasn’t gonna lead where I think you were hoping it would.
Better luck next time…
Regretfully Yours,
Calhoun

Dear Ethnocentric & Vaguely White Supremacist Guy at Caribou

White supremacy is bad, mmkay?

Dear Ethnocentric & Vaguely White Supremacist Guy at Caribou,
Look, I know we came to blows yesterday and the conversation got pretty heated, but ya know what? Today’s a new day.
I hear what you’re saying about “this is America” and “Mexicans should learn to speak goddamn English”, but I gotta say, I’ve got some problems with that logic.
I mean, you realize that this whole debate started with you saying, “Why should I hafta press 1 if I wanna speak to a customer service representative in English?”
… You realize how ridiuclous that is, right? This whole thing started because you didn’t wanna press a number?
Well, you realize that Spanish speakers have to press a number in order to speak to someone in Spanish, don’t you?
I mean, it’s really the same amount of effort on both parts… but in true American spirit, the laziness is undeniable element.
It was where you said “they” were washing away white identity.
Well, for starters, who are “they”? I know I asked you yesterday, but your answer of “Oh, you don’t even know” was a little less than satisfactory.
Furthermore, suppose you’re right and the ubiquitous “they” are deconstructing “white identity” (and that’s a big supposition), are you <i.really gonna act as if white people aren’t guilty of the same crime for centuries? Because we definitely are… but if I’ve learned one thing from our little chance encounter, it’s that ignorance knows no bounds.
You wouldn’t listen yesterday and you probably won’t listen today.
You can keep dreaming of your Aryan brotherhood, but just so you know, things aren’t lookin’ up, so you might wanna let that dream die.
Sincerely,
Calhoun

Dear Handsy Aunt

Dear Handsy Aunt,
Yes, it’s nice to meet you too.
That’s sweet of you to say that you’ve heard a lot about me… unfortunately, I can’t say the same.
Nope, there was no warning whatsoever.
Oh, we’re a family of huggers, are we? Is there seriously no way I can get out of this hug?
Not even if I lied and said that my uncle bad touched me when I was a kid so I don’t like physical affection?
Damn, that was my A-list material too…
Okay, let’s just get this over with… wow, that hand really lingered there, didn’t it?
I admit I may not be the most physically intimate guy out there and sure, maybe I’ve got some weird stuff about touching, but that was definitely uncomfortable for me and just about everybody else in the room.
Okay, I hafta go pretend that I’ve got something else to do… but, really, it was… it was great meeting you.
Sincerely,
Officially Uncomfortable