Diary Of An Entry-Level Try Hard: The Blind Date

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Gil Humplestead is a 23-year-old recent college graduate who finally got his first real job as a Junior Marketing Assistant Coordinator with Incorporated Partners & Co. Today, he chronicles his plans to start his first ever blind date.

My main man, Diary,

Hey dawg. It’s been a rough couple weeks. My “Shark Tank” pitch got denied and then IPC retroactively revoked my 5 percent raise. They say I actually owe the company money now. Thanks a lot, Obama. Might be time to put my “R-money” bumper sticker back on the Hump truck–well, it’s not really a truck, but it’s a 2003 Chevy Trailblazer and some people might consider some SUVs trucks. Still trying to figure out what to do with the dual oversized exhaust pipes I put on it senior year of high school. Might be able to get a little scratch for ’em. Whatever. Won’t matter once I turn 25 and come into Gam-Gam’s inheritance. Should be more than enough to put a down payment on an M3.

Speaking of Gam-Gam, we had Sunday dinner with her. The whole Humplestead clan was there: Gary and Susan, and my idiot brother Harry. Harry’s been on my case lately. He’s also got plans for his own restaurant chain. It would be nowhere near the prowess of Humplestead’s Steak & Scotch, but a future restaurant tycoon always needs to keep his eyes peeled for potential competitors. Harry is a few years older than I am and he’s always bounced around between jobs. He actually worked at IPC right after college, but he started his own business three years ago. He calls himself an “entrepreneur” and drives an Audi A4, but I see through his game. Everything in life is a competition for ol’ Gil, and I’ll be damned if anyone in my family is successful except for me. Harry even offered me a job two months ago. He offered $60k a year, with full bennies and stock options. Had to turn it down. I’m not one for taking handouts, especially from my brother.

Anyway, Gam-Gam was up to her old tricks at dinner. She kept asking me whatever happened to that nice girl I used to date. Well, Gam-Gam, her name is Sharon, and she went back to her home on Whore Island after I broke up with her last year. I guess I’ve never told you much about Sharon. We dated for a few years in and after college, but she was a total six. We talked about getting married and gay stuff like that, but when I told her my plans about being a business tycoon, she acted all weird. She was excited at first, but when I told her I was “open to pretty much anything as long as it made me rich” she kept bugging me with questions. Like I’m supposed to know how I’m gonna get rich? It was going to come to me eventually. I did have that one biz idea I thought was a sure thing, but it turned out to be a bust–the “Brotel: A Hotel for Bros” was going to be a big hit, Diary. I can’t get into specifics, but it was going to pretty much be the JW Marriott for dudes. Can’t talk about it. Sharon thought it was dumb, so we broke up. Three years wasted on a six. Such an amateur move.

Gam-Gam wouldn’t stop pestering me about my love life. She kept talking about how her friend Darlene had a cute little granddaughter that she’s trying to marry off. “Marry off?” Gil Humplestead doesn’t eat the scraps that fall from the table. I’m marrying a virgin who’s crazy in the sack. She was born to know her way around a penis and is yet to be desecrated by another man. I think that’s a pretty fair standard.

So Gam-Gam gave me Darlene’s number and I called her later that night. I figured I’d make her happy. Plus, I’m not about to be written out of the will this close to the final buzzer. Gam-Gam’s probably on her last leg, Diary. That’s just a sad fact of life. If I had to choose between her and seed money for an M-Class, well…you get the point.

I called Darlene after three episodes of “Restaurant Impossible” (research and development) and got the details on her alleged granddaughter. Darlene asked how I was doing and after some small talk (she could die any minute, didn’t want to waste her time) she gave me Stacy’s number. Stacy’s kind of a hot name. I couldn’t find her on LinkedIn, which was pretty disappointing, but also kind of encouraging. We probably didn’t share any connections. Maybe that’s a good thing?

I got this Stacy character on the phone and set up our date. Ruth’s Chris. Standard 9 p.m. rezzie on a Wednesday night–that’s when all the power brokers come out to play. I could tell Stacy was already weak in the knees. Her voice was trembling and she kept stumbling over her words. I have that effect on women. I’d probably go full suit for this one. Stacy sounds hot. Score.

Is she the one, Diary? We’ll find out.


More Gil:
Buying Work Clothes
First Day
Training Seminar
First Sales Call
The Office Party
Hazing The Interns
Company Chili Cookoff
Office Romance
The Holiday Party
Crushing It In 2014
Getting a Raise
Traveling Abroad
Coming Up With a Business Plan

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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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