Confessions of a Delivery Guy

No, this won’t be some kind of exposé of the gritty underbelly of working in a pizza joint. Plenty has been written about the restaurant industry, so I’ll leave that kind of thing up to those who do it best, like Anthony Bourdain in Kitchen Confidential. Even if you’re not curious, you should still read that book. You won’t be sorry. He’s a great writer.

Instead, what I’d like to do is take a brief time-out from my writing about self-publishing, entertainment and well, writing, to tell you about my other job. I haven’t shared too much about it because frankly there isn’t much to tell. It’s about what you’d expect: assemble the order from the grill and the oven, double check them, search the order ticket for hidden clues about additional instructions, triple check the order because TRUST NO ONE, put the order in the car and deliver it. Rinse and repeat.

The people I work with are impressed when they find out I’m a writer, but not terribly curious. They don’t strike me as big readers. After I described Grant Scotland to one guy as a “detective-spy thriller set in a fantasy world” he responded with “Like Sherlock Holmes?” That one put me at a loss for words. In a way, it’s dead on and in another it’s completely off the mark. I guess that tells me that I may be throwing my net a little wide with these books, but it’s my experiment, damn it! I can screw it up as much as I want!


"And if I want a pony, I GET A PONY!"

“And if I want a pony, I GET A PONY!”


Much more goes on in the back of the store, of course, but the simple task of delivery itself is loaded with a bushel of tiny details that make it much more interesting than it appears. Did you know delivery drivers can’t just park wherever they want? I always imagined this was just an unwritten rule for delivery people – if you’ve got a giant illuminated sign on your roof you can shove your car anywhere you want as long as it isn’t blocking traffic. Turns out it’s not true – at least not in Medford. While the police are largely unconcerned with my parking habits, everyone else certainly is. I’ve gotten yelled at by everyone from building superintendents who don’t want me in their fire lanes even if I leave the car running to nosy neighbors who perch at their window and leap out to scold me if I block their driveway.

I still do it, of course, but I try hard not to. Customers don’t want me parking a block away and walking their pizzas to them in freezing temperatures. I don’t get tipped because they’re impressed with my leg work, you know what I’m saying?



“Oh, you walked a mile to give me cold pizza? Please tell me whether I should pity you or punch you.”


So, the approach to the address is always an adventure – as is any sort of driving in Massachusetts – but the exchange at the door is usually very friendly and warm. Everyone is always happy to see me, which is nice. I can go into work feeling mighty low about where I am in my life, but after that first delivery to one of my regulars, I feel a lot better. And I do have regulars. I can tell they like me not just because they make with the smiles and small talk, but also because they tip me more now than they did when I started. So, I got that going for me.


"Which is nice."

“Which is nice.”


There are all sorts of tippers out there. Some make a grand show of tipping you a dollar, others just tell you to keep the change and hand you a twenty on a twelve dollar order. And what kind of tipper am I, you may ask? Average. Thoroughly average. I was that way before and haven’t changed. Average tippers are my bread and butter. On most nights, quantity of deliveries far outweigh trying to jocky other drivers out of delivering to a known good tipper. Relying on capably delivering to average tippers makes receiving a good tip that much more rewarding. It’s gravy on the bread and butter – or like getting a free topping on an already satisfying pie, as the case may be. Additionally, shooting for quantity yields more possible repeat customers. It amazes me how few delivery drivers understand this.

Most of the good (or rather, consistently above average) tippers seem to come from the middle class. Not sure why, but I bet it has something to do with having feet in both worlds of affluence and poverty. They know I need it and they know they can afford it, maybe? Not sure. That’s not to say the poor and the rich don’t tip well – in fact, I’ve received truly great tips from both sets – but they don’t usually tip as well. Not in my experience so far, anyway.

There are some cool experiences I’ve had with my customers. I remember one time I delivered a large family-sized order of pasta and pizza and sides to a house on the day the supreme court ruled it unconstitutional for states to deny gay couples the right to marry. I can’t say for sure the guy who answered the door was gay, but he sure set even my usually obtuse gay-dar off. It was a warm, sunny early summer day and the mood of the whole house was celebratory. Again, I can’t guarantee that I know what they were celebrating, but it was kind of nice to think I was contributing to their joy in some small way. I didn’t say anything, of course, just gave him my standard best smile and bubbliest greeting. Best to keep some professional distance, I think. Try to get too friendly and things could get awkward fast. Awkward deliveries don’t seem like they’d yield a repeat customer.

And the pets are usually pretty fun, too. For some reason, I’ve always been a bit of a cat whisperer. Felines are somehow drawn to me (hopefully not because I smell like cat food, although sniffing today’s/yesterday’s shirt confirms this may be a possibility) and this provides a source of amazement from a new customer whose cat is walking right up to me and talking to me and trying to follow me back to my car. Dogs, on the other hand, are a mixed bag. Apart from being excited about the food, sometimes they like me and sometimes they want to lunge at my throat. I just watch the body language and proceed accordingly. But cats for some reason always greet me like we’re old friends.


"Do not trust them, daddy. They care only for their bowls. They don't love you like I love you."

“Do not trust them, daddy. They care only for their bowls. They don’t love you like I love you.”


There are also some bittersweet moments with customers, which was something I absolutely was not prepared for when I took the job. Apparently, there’s a lot of public housing in Medford and a good portion is inhabited by the old and infirm. Delivering to them is both rewarding and troubling and for almost identical reasons. On the one hand, they are all terrifically sweet and welcoming. Even though I’ve learned I probably shouldn’t ask “How are you?” – because they’ll tell me, although usually they spare me the details – but I still do anyway. I set up the food for them if they need it and get to leave with a feeling akin to doing a good deed. Some of the drivers hate delivering to them, because the tips are poor to middling at best, but I don’t mind so much.

On the other hand, it sucks when you lose a regular customer and there’s little doubt as to why. It’s not uncommon to pull up to public housing and see young men and women moving furniture out to the curb. It certainly isn’t moving day. The only way people move out of places like that is feet first.

One lady, who was an extraordinarily generous tipper, asked me at one point if I wouldn’t mind in the future coming in and setting up her food for her. Since I’d already done this for others I thought nothing of it and told her yes. She told me she wouldn’t ask me, except she was dying and soon wouldn’t be able to leave her bed. I didn’t know what to say to that. It surprised me. She seemed far more full of life than most of the other old and sick. So, I just offered her my sympathy and told her I’d be happy to help her out next time she ordered.

Except there never was a next time. That was the last I ever saw of her. I still deliver to another regular in the same facility, except he’s located at the exact opposite end from where she was. I don’t know if he knew her and I don’t want to ask. I don’t think it’s something anyone there needs to be reminded of. Instead, he and I talk about the Patriots.


In Massachusetts, at least, Tom Brady is a uniter, not a divider.

In Massachusetts, at least, Tom Brady is a uniter, not a divider.


So, that’s it. I don’t have much more to say about delivery, except that it’s proven to be much more interesting, even fulfilling, than I had thought when I started. I guess I wanted to share some thoughts about that.

Thanks for indulging me! Hope you weren’t bored.

This week’s T-Shirt winner is Arthur Dampier! Congrats, Arthur! Be sure to respond to the newsletter with preferred size and where it should be sent.

See you next week, everyone! I’ll have some notes about Wayward Daughter’s New Year’s promotion for you. Until then, do the thing with the books and the food and such.



One thought on “Confessions of a Delivery Guy

  1. Pingback: Further Confessions of a Delivery Guy | This Tone of Voice

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