Diary Of An Entry-Level Employee That’s Trying Too Hard: Office Romance


Gil Humplestead is a 23-year-old, recent college graduate who just got his first real job as a Junior Marketing Assistant Coordinator with Incorporated Partners & Co. Today, he chronicles his first brush with romance in the workplace.

Monday, December 2, 2013

Hey, Diary. It’s me, Gil.

It’s been a rough couple of weeks/months. I don’t really want to get into specifics, but the bone sled has been a little empty, lately. The bone sled is what I call my bed. It’s a sleigh-style bed from IKEA, so I call it the bone sled.

Ever since breaking up with my college piece, I haven’t had the success I was used to in the past. Gil used to bed dimes on the nightly, that is until I started dating a six like some type of idiot. Sharon was a real sweetheart and she always got my Chipotle order right, but we started growing apart when I forgot her birthday two years in a row. If I’m ever gonna become the CEO of one of Mark Cuban’s companies, I can’t be tied down. Sharon could never understand that.

I thought after college I’d be slaying even more strange than I did in college. I would have money, cars and power. Stuff that women really dig. I was done with girls right when I got my diploma. But I go out three nights a week and still can’t close on the hotties that I used to. It’s like there’s something holding me back. I put my best foot forward every night. I put on my Ferragamo loafers one foot at a time, just like everyone else. Maybe I need to overhaul my wardrobe to look like I make more money. I might have to take out another credit card, but it’d probably be worth it, because of all the tight slizz I’d start pulling.

Loneliness can get the best of a man, diary. The Brazzers gold membership I bought last month is okay, I guess, but I’m a flesh and blood man. I need to be desired. I need to be coveted. I crave human touch. I can see my obituary now: “One-time international sex symbol, Gilbert T. Humplestead, died yesterday, alone in his bed, with no chicks around.” It would be such a disappointment. What would my father, Gary Humplestead, think? Gary locked down Susan Barnett-Humplestead when he was my age. He expects the best out of me and I’m blowing it. Straight blowing it.

Desperation is a cheap cologne, Diary. By no means am I going to lower myself to a lesser standard when it comes to bringing lady callers back to the bone sled. But sometimes, even a hunk like Gil Humplestead has to call in a slumpbuster.

We had our monthly company happy hour at Dave & Buster’s last week, and I was on the prowl. I was hoping there were gonna be some babes there who I could impress with my skee-ball skills, but no dice. Apparently, Dave & Buster’s isn’t exactly the go-to spot for slampieces at 6pm on a Tuesday. I played a few games of air hockey with one of the interns. I forget his name. He beat me twice, but I made up for it by chugging in his face after he beat me the second time.

I decided to take a power lap after dropping a five-spot into the Time Crisis machine. My boss Terry was putting on an embarrassing display of dancing on one of the Dance Dance Revolution machines, so I saw it as an opening to seduce the females in attendance through the power of dance.

I hopped up on the machine next to Terry and threw down the gauntlet. Little did Terry know that I had spent a little time on a national circuit of competitive Dance Dance Revolutioning. I used to sneak into the student center late at night to practice my moves. Sure enough, I destroyed Terry in a superior display of manhood and beat him by 10,000 points.

I hopped off the machine to high fives and pats on the back from my coworkers. I rolled my ankle as I was coming off the machine, but I played it off and made it look cool, like I was about to bust into a freestyle dance routine, like I’ve been known to do. It was just like the ending of Dirty Dancing. I headed to the bar to get a celebratory Humplemaker. It’s like a boilermaker, but instead of a beer and shot of whiskey, it’s a Miller 64 and a shot of peach schnapps. Really gets me going.

I was on my third Humplemaker of the night when Clara from accounting came up to me and complimented me on my phenomenal footspeed, as it pertained to DDR. I played it cool for the most part, but really soaked in the praise at the same time. I think she’s had a crush on me for a while now, like most of the women in the office. Clara is in her mid-30s, twice divorced and I wouldn’t classify her as “fat,” but she’s not exactly fit either. She wears really baggy clothes, so I really never knew what she might look like underneath her oversized wool sweaters and ankle-length dresses.

I ordered a round of Humplemakers as Clara from accounting parked herself next to me at the bar. I talked to her as she stared into my piercing eyes, hanging on every word that came out of my mouth. I dazzled her with my plans for Humplestead’s Steak & Scotch House and told her that I planned on being a millionaire before I turned 30. She recognized that I am a man on the fast track to success. I was fanning her flames of desire with every grand business scheme I laid on her.

“Gil, you’re so driven. I can’t think of any other man with so much promise at such a young age,” she said as I filled her glass with another pour from my pitcher of scotch and Pibb Xtra. She gazed into my eyes as her chins jiggled with laughter after each of my jokes.

Three pitchers of scotch and Pibb Xtra later, we were the only people left at D&B’s. It was my time to shine. I can close with the best of them, but right as I closed out my tab, Clara had grabbed me by the collar and laid a fat kiss on me. It wasn’t a kiss, so much as it was her trying to swallow my entire face with her mouth. Her mouth tasted like an exotic mixture of Diet Coke, chicken fingers and old cigarettes. The lust between us was overpowering.

The bartender ushered us outside where we waited for our cabs. This was my chance to break a lengthy dry spell, Diary.

I’ll have to finish this up later, bro. A Bar Rescue marathon just started on SpikeTV.



More Gil:
Buying Work Clothes
First Day
Training Seminar
First Sales Call
The Office Party
Hazing The Interns
Company Chili Cookoff

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Brian McGannon

What do I love? I love happy hour, a good golf tan, and getting moderately drunk during dinner.

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