"I don't want to sell anything, buy anything or process anything ... I don't want to sell anything bought or processed, or buy anything sold or processed, or process anything sold, bought or processed, or repair anything sold, bought or processed." - Lloyd Dobler (John Cusack) in "Say Anything"

Every time I sell something online I vow to never do it again. Not because I’m worried about getting murdered by a stranger – well OK, maybe that’s a small part of it – but because the process is a massive pain in the ass that usually leads to nominal compensation.

Somehow I always forget the horror of this experience and find myself posting a kitchen appliance (used once!) or futon chair or item that may or may not be an antique because I’m certain there’s someone out there who wants to pay cash for my trash. And there usually is, which is why I stay trapped in this cycle of online selling.

After years of web-based wheeling and dealing, I've learned a thing or two to minimize the migraines. I am always honest about the item, list it on the low side and don’t haggle. Here is the item, this is the price, do you want it – yes or no?

This does make the process a little smoother, but most of the time I still want to throw my laptop into the river after the first three inquiries. And buying through online sites is a hassle at best, too. Just Google "CraigsList nightmares" and you might consider a life of Luddite-ism.

Thus, here are some reasons why not to buy or sell anything online no matter what – and one reason why I can’t stop / won’t stop.

Why not to:

1. Safety – Although nasty, creepy and violent online-selling stories exist, I’ve never had any questionable safety issues, and I always meet in public places to make a transaction. I did once have a man ask me if the contents of the car were included in the sale which seemed a little off to me. Or maybe he just really wanted that crumb-covered booster seat and iPod Nano.

2. Dumb questions and comments – This is quite possibly the part of the process that has the potential to push me over the edge the fastest. I posted a never-used KitchenAid mixer to Facebook Marketplace with three photos and all of the details, including the color (white). Within 10 minutes, I received a dozen responses, including one that said "I want this, but in red."

3. Never-ending inquiries – I always delete my items after they sell, but for some reason, the ad for my ’75 Eldorado from 2016 is still floating out there in the Internet wasteland today and I got an inquiry about it as recent as April. Sorry, Gary, but the Caddy is long gone.

4. Time loss – You might recoup some of your money, but you’ll never get back the time spent on trying to sell your sh-t to strangers. The time it takes to write the ads, take and upload the photos, field inquiries both intelligent and inane and then meet with a possible buyer really cuts into profits and can put your psyche in the red. Plus, no-shows are a reality and a drag.

Why I won't stop:

1. Yard Yahtzee – And yet there is one reason why I will probably never cease the online hustling and it has to do with my recent acquisition of a lawn game. True story. I saw an oversized version of Yahtzee for sale on Facebook Marketplace and I was immediately interested. Yahtzee has always been a family favorite just after cribbage and for $15 I thought even if we played it in our yard once it was still cheaper than most forms of family entertainment. 



So I inquired, found out it was available and set up a time with the seller to meet in an Office Max parking lot. I was a little skeptical that the game had been excavated from grandma’s basement and might still smell like it, but oversized Yahtzee?! I was willing to take that risk.

My partner and I got to the lot about 10 minutes before the meeting time. We noticed that there were already 4 or 5 parked cars with drivers who also seemed to be waiting for something. Within five minutes, more cars pulled into the lot until eventually there were 16 cars that were clearly not in the lot for office supplies.

Finally, a silver vehicle pulled up and two people got out and started unloading numerous Yard Yahtzee games onto the parking lot. They had dozens of them, all crafted by the father-and-son team (the dice are made of sanded wood chunks so maybe they are carpenters?) and they had sold dozens.

People started streaming out of cars with  smiles on their faces and money in hand, many asking the same questions, "Did you make these?" "Can I buy another set?" I purchased my set and then we stood back and just watched the scene. It was so strange and random and positive – quite possibly online buying and selling at its very best.