The Weirdest People I Met As A Postmates Courier

When Uber came on the scene in 2009, it revolutionized the idea of “convenience at cost.”

Customers saved tons of money using Uber instead of a regular taxi, while Uber drivers made an extra buck on the side driving whenever they could. Two years later, a company that specialized in delivering a variety of goods (with an emphasis on food) was born. I worked as a Postmates courier for a few months, and much like taxi drivers (and now Uber drivers), I was lucky enough to witness some crazy shit.

Drunken Nightfall Construction Man

My first delivery ever proved to be a strange one, to say the least. I had turned on my courier app and after only a few short minutes, a request came in. I clicked accept and raced to my car. The order called for a small lamp, a hammer and a 30 pack of Bud Light. I was confused and curious, but my job is to deliver the goods, not interrogate people on their seemingly weird intentions. I picked up all three items from Wal-Mart then headed to the customer’s house. I rang the doorbell, and a man wearing only paint-covered overalls and a face shield opened the door. I handed him his belongings, he signed for them, then smiled at me and closed the door. A strange way to start my career as a courier, to be certain. To this day I still wonder what the hell he was building back there, but I’ve seen Dexter enough times to know you don’t mess with a man holding a hammer and wearing a face shield.

The Recluse

Once when delivering in Irvine, I dropped a burger and fries off at an apartment housing a very trepid man. I rang the doorbell and waited for about 20 seconds. As I turned to walk away, I heard the door creaking open. I turn back around to see the creepiest eyeball I’ve ever seen staring back at me. His eye kept darting wildly back and forth between my face and his bag of food.

“Oh, um, hello sir. I’m Sean, I work for Postmates, I have a delivery for you.”

“Leave it.”

“I’m sorry?”

“Leave it on the doorstep!”

I walked back towards the door to leave his food where people normally have welcome mats. I dropped the bag on the floor in front of the door.

“Ok, sir, but I still need you to sign here so that it’s documented that you received your del–”

“Sign it yourself, give whatever tip you want.”

After he slammed the door shut, I began briskly walking to my car while signing away the $50 tip this man just gave me, because I’ve seen Dexter enough times to know you don’t mess with people that are that secretive. Damn, I need to start watching a new show.

The Sorority Girls

I got a request for six bottles of champagne once. I walked up to the front door of the house and rang the doorbell. You’d think I’d died and went to heaven, because seven or eight scantily-clad women opened the door and all started praising my name, like I had just saved them from Armageddon. They loved me so much that they even invited me inside to party with them. Keep in mind, I have yet to say anything at this point, considering how hard it is to speak over the chorus of “woot woot!” Eventually when they quieted down, I explained to them that I was low on cash and really needed to make some money, so I politely declined. I still consider it one of the most boneheaded blunders ever committed in the history of the world.

The Gamers

On one of my last trips ever was a request for several bags of candy and a 24-pack of Coca-Cola. When I arrived at the house, I was greeted by a friendly young man in a large Dragon Ball Z t-shirt. Society would call this type of person a “nerd.” As I handed him his candy and soda, I managed to peek inside his apartment. There was a long table with 7 or 8 other guys on it, all playing the same game on their laptop, a game called League of Legends. Around the boys was a sea of candy wrappers and a variety of crushed cans, ranging from Mountain Dew to Red Bull.

“Hey driver guy, you ever play League of Legends? You wanna play? We need one more player, we have an extra laptop and everything. It’ll be super sick man.”

“Ummm…alright, maybe one game.”

Four hours later, I was finally on my way home with a stomach ache, a brand new League of Legends account, and a sudden realization that I, too, am one of these “nerds.” Postmates taught me that I draw the line at potential serial killers and beautiful women, but nerds are my weakness. Dexter would be disappointed.

The Dildo Connoisseur

I once received an order that required five or six double takes from me before I accepted the request. After rubbing my eyes cartoonishly, I looked down again and realized it was real.

Some guy named Charlie wanted me to deliver an 18″ double-sided dildo to him from Condom Revolution.

Penis delivery. This is my life now.

I got to ConRev and lo and behold, there she blew, all 18 veiny inches of her. The wall was adorned with a variety of different shapes, sizes, materials and colors. I was beginning to feel awkward and remarkably ill-equipped, so I grabbed the $50 dildo and took it to the checkout counter.

The first thing I did was inform the employee (who actually looked like she meant to work at Hot Topic and just got lost) that the monstrosity in my hands was not for me and was for a friend. Only later did I realize how poorly I chose my words, considering that it was a double-sided dildo. She didn’t even try to hide the fact that she didn’t believe me.

I purchased the Gut Blender, which thankfully came in a very large, opaque bag and informed the customer that I was on my way. When I got there, he greeted me outside of his home.

“HA HA HA! Oh my god, I can’t believe you picked it up! You actually bought it! That’s so funny.”

“I’m sorry?”

“Oh, I just ordered it as a joke, to see if you would actually buy it or not, and you did! It was totally just an experiment.”

“Oh, ok. Well, do you still want it?”

“Yeah, I mean…I guess so, since I paid for it. Might as well. Maybe I’ll melt it down and make a tire out of it.”

Suddenly the look on the ConRev employee’s face when I was purchasing the dildo made perfect sense.

Leader Image Photo Credit: Postmates