"I like doing this almost for what it is, rather than what you get," Scott tells me after expertly climbing out of a dumpster at Montreal's Jean-Talon market last summer, wearing jorts and a tattered undershirt. "I do this because I'm poor, man," he says with a smirk. "Nothing bad has happened so far."

The next dumpster over yields a few usable cherries. "That's enough to mix some booze with," says Patrick, Scott's companion, who is on his first such foray. He takes a bit of coaxing, but eventually he take his first dive. "Urban foraging, that's what this is," he later tells me. When I run into him again the next week he is by himself, and has the technique down pat—along with a philosophy: "For me, it's a lifestyle thing."

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An FAO study on food spoilage from 2008 estimated that each year, 12% of the North American fruit and vegetable crop is lost at the distribution stage. (Another 28% rots away in your fridge.) That's what these dumpster divers in whose company I had insinuated myself were after. I was out to meet some of these freegans and to hopefully score some free produce in the process.

Scott and Patrick let me tag along. Though my black skinny jeans (RIP) were covered in bike grease, I had basically zero interest in climbing in. One dumpster was just plums all the way down, great for jam, but none of us had the means or desire to take more than a few. Slowly, our boxes and bags fill up and we have as much as we can comfortably carry.

Our foraging complete, we withdraw to a nearby sidewalk to sort and divvy up our take. They hand me some artichoke, celery, and zucchini, and leave half of the yellow beans behind for future scavengers. My backpack bulges with produce, enough for a week's worth of soups and stews. (I have no idea what to do with artichoke, and throw it out a month later.)

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Just then, a group of respectable-looking shoppers walks past. "What's going on?," a lady wonders aloud, pauses, and brands us with the most obvious pejorative: "Hipsters!"

That was last year. That was before I set out to cut my monthly living expenses by 60–70% so I could, you know, follow my passions. And while this meant no dumpstering for me personally, at least for a while, I lived with people who did.

There was Valérie – one of those free-spirited rainbow kids who dance at psy raves completely sober until nine in the morning – who basically built scavenging into her daily routine. There was Thomas the couch surfer – a hereditary French baron fallen on hard times after dabbling in too many letters of the alphabet (particularly the ones in the middle) – who once during his stay nicked a $12-slice of fine French brie and called it an act of liberation. Together, they were a formidable duo and would regularly turn up with boxes of discarded organic produce from dumpsters behind neighbourhood health food stores, including, once, a whole box of gluten-free chips. They were stale.

But there was a dark side to all this, since we weren't the most diligent in processing our half-rotten bounty after the initial flurry of smoothies, stews, or jam. Discarded tea leaves and veggies would plug up the sinks, turning them into cesspools of dirty dishes. One missed garbage pick-up meant piles of reeking, leaking trash bags. It did not help that our fridge was barely functional: the freezer was a fridge at best and the fridge was more of a cooler where dumpstered produce spoiled, releasing black sludgy liquids that would harden to a crust. Fruit flies, once established, proved nearly impossible to eradicate. It was easier to simply move out, in the end.

And now there's Tim, the 50-year-old roommate who paints—and trades speculative stocks on margin. I was floored when he returned from his first foraging foray with several packs of chicken. "It expires tomorrow!" he crowed. (We ate it and lived to tell the tale.)

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His MO is completely different. He'll go into a bakery, or butcher shop, or mom-and-pop grocery store and ask for items that will be discarded soon. Often he leaves empty-handed but sometimes he strikes gold, and when he does, he makes sure to leave a tip.

"My $2.35 is gone but I got $6 worth of veal for it!" he shouted while exiting a grocery store on a recent afternoon with a duffel bag full of ancient canned goods under his arm. "See? Four o'clock is a good time." I pocketed my iPhone and dumped the bag into my adult tricycle's rear basket. (The trike in question, which lay abandoned in an alley and belonged to a long-time Mile-End street person who passed away last winter, was another Tim Find.)

He pulls it off because he is charming, reasonably presentable, and always has an anecdote or compliment at the ready, which allows him to immediately connect with people. To store owners, he will gently explain how he has only $25 left until the end of the month (often true) and also ask if they're hiring. With other freegans, he is always ready to trade on-the-ground intelligence, to barter, and to share excess items.

It would be poor form to discuss dumpster diving without acknowledging that it does entail a certain level of privilege. This is often paired with a certain sense of entitlement among those that practice it. People who are able to show up on a schedule at (or behind) a place of business do not necessarily qualify as being among society's neediest, in my books. There's a fine line between scavenging and asking for freebies, and going into stores before closing time to ask for things because "You're throwing them out anyway!" begins to blur that distinction.

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And it would be hypocritical of me not to acknowledge that I have benefited of late off the inefficiencies in the First World's food supply-chain. In fact, these past few weeks I have eaten more fruit smoothies and roasted vegetables than I can remember. It sure beats a diet built around cheap convenience foods such as mac 'n cheese, ramen, or even just beans, lentils, and rice. Still, it takes some humility to lower yourself into a fetid plastic box to compete with flies and wasps over the least mushy tomatoes. But evidently, there are those that can stomach it.

They, the dumpster divers, are not the people who need to "eat for free"; they are the people who simply choose to do so.

9 Do's & Don'ts for Dumpster Diving

DO become aware that living off the inefficiencies of our food supply chain is a lot of work; you have to forage daily. A bike helps. An adult trike – which allows you to stand on the pedals and peek into dumpsters as you coast past and to use it as a platform to reach into them – is even better.

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DON'T ever think of even looking for meat in the trash. (Although Scott said he's recovered frozen cheese and meat in winter, adding: "I should probably stop doing that.")

DO become friendly with the vendors at the market. Crossing paths with some of them as they are going to throw things out can get you bunches of parsley or dill, or a dozen cobs of boiled corn which didn't sell. Sometimes, you just need to ask.

DON'T take more than you need; if you do, leave some beside the dumpsters for others. And don't leave a mess.

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DO avoid the security guards at public markets. But other market employees can be helpful: a fork lift dude at Jean-Talon market offered tips (forage around 3 pm on Saturdays) and gossiped that unscrupulous restaurant operators might be sourcing some of their produce from market dumpsters.

DON'T dumpster dive lettuce. Once off the stalk, lettuce leaves get yucky fast.

DO make friends with other freegan types, barter with them, and share tips with them.

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DON'T try to rely on this as your main source of food; you might starve. While you can easily meet your fruit and vegetable needs during the months of plenty, you'll still have to shell out for high-quality protein and carbs. And you have to be flexible about what you're willing to cook, depending on what you find.

DO own a good vegetable peeler. You'll need it. And triage, process, or cook what you find promptly, because most produce will spoil really fast.

[Images by author; this post is based on a thing I wrote last year for a now-defunct Montreal blog]