Diary Of An Entry Level Try-Hard: Budding Romance

Screen Shot 2014-04-21 at 5.35.01 PM

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 latest romantic endeavor.


Man, am I glad to see you. I know it’s been a while. Ol’ Gil’s gotten himself into a bit of trouble with the womenfolk. It’s a long story, but one worth telling, much like my future best-selling business book, “On My Way To The Top And How I Got There: A Business Manual For Young, Up-And-Coming Sharks And Bulls” by Gilbert T. Humplsestead, Sr. It’d be so cool if they put it next to Jon Taffer’s “Raise The Bar” in airports. I’ve read that thing cover to cover at least five times already–I knew those 30 minute #2 breaks would pay off eventually.

Anyway, last time I talked to you, I was talking about my upcoming date that was set up by Gam-Gam with her friend Darlene’s granddaughter, Stacy. I found Stacy on Facebook a few days before our date, and my God, she did not disappoint. I cranked to her 2011 SB pics at least six times. She’s this hot little blonde number with dece chest hammers and a knockout smile. Her personality wouldn’t even matter. Gil don’t care.

So I called Ruth’s Chris on Monday and made the reservation for 9 p.m. Wednesday. RC’s would probably be abuzz with wheeling and dealing high rollers. You can’t underestimate the value of a good facetime sesh at peak power hours, even if it is when you’re on a first date. I can almost picture the scene when I walk in with Stacy on my arm.

“Whoa. Who’s this new hotshot with the dimepiece?” “Where’s that guy work out?” “What’s that hair style called? I want it.” “I’d have sex with that dude, but he probably isn’t gay.”

I just can’t believe it, Diary. Behind every good man is a good woman, and hopefully Stacy would be on top of me before she was behind me, because that would mean that I scored. Stacy was the hottest chick I’ve ever gone on a date with. Total smokeshow. I mean, I thought I was in love the moment I saw her. The Gilman doesn’t fall so easy.

Couldn’t even stay focused at work on Wednesday. I stared at Stacy’s FB profile all day. Even found her public Instagram account. So hot. I had to make a great first impression. The Hump Truck is usually money with the ladies, but sometimes you have to go all out–so I did. Called up Enterprise Rent-A-Car on Wednesday to check out what kind of “exotic” rides they had available on short notice. Just my luck, the gods of trim were certainly smiling down upon me. The toughest decision I had to make all day was whether to go with the Audi R8, Yukon Denali, or E350 Benzo. After three hours of deciding which one would make me look the most baller, I settled on the Audi R8. Yeah, the Yukon was American and had a sick back seat for making out, and I’m pretty sure I read that Zuckerberg was spotted cruising in an E350 last month, but the R8 is such a TGM (Total Gil Move). I’m all about American muscle through and through, but I just wanted a taste of the forbidden German fruit before I have an entire fleet of American-made luxury vehicles. Or better yet, give the Germans a taste of “The GILtimidator’s” driving style. I’m not driving. I’m qualifying.

I picked up the R8 from the rental place around 7 p.m. and they told me I could have it for four hours–pretty good deal at just $75 bucks an hour. I thought Stacy might cause a flash flood on her block when I rolled up on her in the R8.

I made sure I hit up the ATM before picking up Stacy. There was no way I wasn’t paying for this dinner with a huge stack of Jacksons.

Rolled up on Stacy’s apartment around 8:30 and honked the horn. It took me a while to find the horn on the steering wheel. Damn Europeans. You should just be able to smack the middle of the steering wheel and belt out masculine horn blast.

She looked amazing. Of course, I got out and immediately went in for the hug. Stacy was wearing this tight little black number with heels. She wanted to impress. I had gone with the trusty camel hair blazer, bootcut Wranglers and Cole Haan loafies. We were on our way.

We were seated in the middle of the room, per my request. Was a little disappointed with the Wednesday night turnout at RC’s, but regardless, I was going to charm the pants off of her. The waiter asked what we wanted to start out with and I let her order. She went with vodka on the rocks with a twist. So hot. I went with scotch, like a true power player. We made small talk for a while. I was a little miffed that she didn’t ask me how much money I made in a year before taxes, or how I could afford an R8. She asked me about college, so I rattled off my favorite TFMs from 2012 for her and how many frat moves I pulled in college. She giggled at a couple of them and was looking around the restaurant a lot, probably because she wanted to see that she was being seen with me.

The waiter finally asked us for our food orders, so I went with my usual bleu cheese wedge to start, along with a Crabtini app and the Cowboy Ribeye. I then looked Stacy deep in the eyes, and with the power of a thousand board members, said, “She’ll have a salad. Dressing on the side. House vinaigrette?”

Stacy looked at me, completely taken aback. I’m shocked she didn’t just melt into her chair right there. She added a petite filet to her order and I let her share some of my Crabtini, but she was pretty quiet after we ordered. I think she was intimidated. Understandable.

She excused herself shortly after dinner to go to the restroom, obviously to pleasure herself after basking in the glow of Gil Humplestead incarnate for an hour and a half. After she was gone for 10 minutes, I got a little worried. There is such a thing as too much Crabtini.

I got the bill and wanted to wait so I could pay it in front of Stacy, but she sent me a text. “hey wasn’t feeling well so grabbed a taxi and went home thanks.”

I walked out of the restaurant dejected. $147.53 down the drain, not including what I paid for the R8. I kept my head up as I handed over the rest of my cash to the valet and sat behind the wheel of the R8. Hadn’t felt this wrecked since Whitney Vance turned me down for formal sophomore year in a Facebook message.

I’ll have to move on from this one, Diary. Gil Humplestead isn’t one to get hung up on some chick. The Bone Sled will soon fly high again.

All in,


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
The Blind Date

Email this to a friend

Brian McGannon

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

5 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More