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Guide to Dumpster Diving
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GEAR
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Shit you need: 
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Flashlight (headlamp preferred
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Dark, unmarked clothing, preferably thick
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Gloves
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A pole, 4-6 feet long
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Shit that's nice to have:
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GPS/Smartphone for marking good locations
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Lockpicks/bolt cutters, if you don't mind breaking laws
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It's a good idea to always bring a buddy. Admittedly, most of my diving has been solo, but I know my neighborhood well. Bringing a friend can get you out of nasty situations, even though you generally have to split whatever loot you get. 
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METHODS
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Find a dumpster. Open it up. Look inside. Some have sliding doors on the side, these are generally too tall to climb in through the top, but you can climb in the doors unless you're a fat fuck. The doors also make it easier to rummage around. Some only have top doors, these are also fine. Don't fuck with compactors, even if you manage to get inside, you'll probably die (not even joking, those things are serious business). 
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I always poke around with my stick before I climb in. I only climb in if it looks like there's good shit to be had. I avoid anything that smells too bad, dumpsters with food are fucking gross. Keep away. 
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Oh, and only go at night. No matter what, you're going to look sketchy as fuck, and it's better to go when there's nobody around to call the cops on you.
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LEGALITY
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There are four things that can get you in trouble diving:
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-Stealing peoples personal info
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-Bypassing a lock to get into the dumpster
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-Ignoring "No Trespassing" signs
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-Local ordinances prohibiting it
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Anything in the garbage is considered public domain. That said, if you find someone's credit card info, you're still guilty of identity theft.
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If you're bypassing a lock, technically you're breaking and entering or some shit. It's illegal, don't do it if you don't want to take the risk. And if you do, at least be fucking subtle about it. 
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If there's a "No Tresspassing" sign, the owner is a royal cunt, but you could still get in trouble. I've never seen a sign before though, so it's not a major concern.
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If there's a local ordinance, your call. I don't even check before I go to a new town. If you get in trouble, most cops will be fine if you just tell them that you didn't know and that you'll stop. Your choice if you want to risk it.
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LOCATIONS
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The best places to dive are office supply stores, computer repair places, etc. 
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The best places to dive are office supply stores, computer repair places, etc. Not only is the loot good, but there's little to no organic trash, so it doesn't reek. 
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Staples is usually amazing, I'm sitting on an office chair that I got the second time I ever went diving. It looked like it had been returned because of a single small scrape on the back of the chair. All of the parts were still sealed in the original plastic. 
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Best Buy is great, if you can get in. They have a tendency to lock their dumpsters, because their employees are jews and would steal shit by throwing it out and retrieving it from the dumpster later. They're retards, too, because you can do a whole lot better just going through what's normally thrown out without getting your ass sued. I've only gotten into one Best Buy dumpster, but I was rewarded with cat5 cable, a GeekSquad jacket (which I left because I'm not a faggot), a plethora of coax and cat5 connectors and extenders, and about a hundred blank DVDs. 
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I've heard OfficeMax is good, never been to one myself.
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Strip malls are great because you can just drive behind and check out all the dumpsters. Found a xbox 360 last time I hit up a mall. 
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FOOD
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How fucking poor are you? Seriously, you have internet but you're diving for food? Get your priorities straight.
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Dumpsters with food are fucking disgusting and as a rule are best avoided. The only time I've taken food from a dumpster was when I found three pounds of candy bars that had expired the week before. All still sealed, with price stickers on them. Shit was pretty cash, but I'd never take food otherwise.
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Dumpsters with food are fucking disgusting and as a rule are best avoided. The only time I've taken food from a dumpster was when I found three pounds of candy bars that had expired the week before. All still sealed, with price stickers on them. Shit was pretty cash, but I'd never take food otherwise.
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HAZARDS
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You're in a fucking dumpster, be careful. There's a reason you're supposed to wear gloves. Your absolute worst-case scenario is finding used needles (I never have). Second worst-case scenario is finding a major biohazard (a guy I know online found a dead baby once, had to call the cops, turned out the mother was a crack addict and dumped the baby a day before). Always probe around with your stick first. Your stick is your best friend.
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EPILOGUE
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You can make fat stacks if you dedicate a lot of time to diving and get to know your area. Get a feel for what kinds of places have the best loot. Be careful. Avoid cops. Electronics are good. Avoid homeless people. People throw out a lot of perfectly good stuff, and you can either use it or turn it into either dosh in your pocket. 
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Happy diving!