31 Pizza Deliverers Share Their Most Awkward Delivery Experiences

22. Delivered to prostitutes, met a friend.

Did delivery to the local hooker hotels around the restaurant I worked at in high school. Often the girl/women would answer the door naked and flirt etc with me. One young cute girl as far as I could tell lived in a room on the top floor and used another room for work. I delivered to her 2-3 times a week and one day she told me to come back after work and drink some beer and hang out. She told me about her life and man did it sound like shit, abusive step father raped then kicked her out, started doing heroin, kicked it, moved half way across the country to stay with family only to have more abuse. And here she was getting by but barely and was planning on moving South to Florida. We met up weekly for a few months and just talked. One day she said she was ready to go and that she wanted me to go with her. I told her I couldn’t, just started my junior year of high school and wanted to finish. We said goodbye later that night and I never saw her again.

23. A customer who couldn’t carry the pizza because she was apparently beaten so badly.

I used to work for Papa Johns in a not-that-great neighborhood of Chicago (Uptown, if anyone’s wondering). Anyway, I get to this woman’s house on my first week of driving and she answers, asking if I can come in to set the pizza down on the table. I politely inform her that it’s against company policy (I half thought it was a mystery shopper because we always get graded on delivery pepperoni pizza, which is what she ordered so I made sure not to go in). She then decides to tell me that she can’t hold the pizza because her boyfriend just beat her so badly that she was in the hospital. I look behind her and there’s a dude just standing there staring at me, no idea if it was the boyfriend but another girl appeared out of nowhere, took the pizza, handed me a tip and closed the door. I think I just stood outside the door for a good few minutes wondering if I should be telling anyone about this domestic violence confession.

24. Somehow found himself in the middle of an argument.

A horribly heated and evidently unplanned discussion about child support. When I showed up, with not only pizza but wings and an overpriced 2-liter, I was used as ammunition that she was not spending what he gave her wisely.

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