What’s Your Most Memorable Craigslist Experience?

One of the most valuable lessons I’ve learned is to donate, sell, or throw out things that I haven’t used in a long time, don’t currently use, and probably won’t use in the future. I call this the past, present, and future method of house cleaning, and it has served me well.

Lately, I’ve been selling a bunch of old stuff on Craigslist for the first time in a while and was reminded of the sheer volume of absolute lunatics on the platform. So I decided to recruit some fellow bloggers to hear their tales of Craigslist insanity. I simply asked them what their most memorable or strangest interaction was like on Craigslist.

Here’s what they had to say…

Sharon Rosenblatt, Director of Communications, Accessibility Partners, LLC

Hi Chad,

I have two Craigslist stories if you’re interested:

I went to pick up a Craigslist purchase (Guitar Hero games) on a work lunch break a few years back (Must have been 2011 because I was 22 or 23). The woman seemed nice enough on the phone, and when I got there, I expected just to hand her cash and be on my way. Instead, she seems to like that I had a job and hollers up the stairs to wake up her unemployed son. As I wait on the front steps, she drags him out of bed (it’s about 12:30) and says that because I’m buying his Guitar Hero games, he and I have a lot in common and should grab a coffee. I told her I had to run back to work. She had my phone number, and I was terrified she was going to make her son call me and ask me out, so I could get him out of the house as well, beyond his old video games.

I also found amazing roommates on Craigslist (the Washington Post liked this story).

I never realized how contentious it was to move in with strangers! When I graduated college in 2010, I knew I wanted a fresh start. A lot of my friends didn’t know what they were going to do, and the unpredictability scared me. So, I took a total leap of faith and found a sublet on Craigslist in Silver Spring, Maryland. It was a bit unconventional, as my new roommates would be guys in their mid-30s. But, I made sure they had stable employment and that the house was clean. I went with my gut despite protests from my friends that it was weird for a 22-year-old woman to move into a frat house. It worked so well that even though we’ve all gone our separate ways by now in different states, I still talk to them fairly regularly via text. Also, as with meeting anyone online, it doesn’t hurt to do a quick check for sexual offenders in your neighborhood. Sounds graphic, but I didn’t want to find out after the fact that one of the guys was on “To Catch a Predator”.

Gary P. Cubeta, Insurance for Final Expense

I have a home theater in my house here in Scottsdale, Arizona.  I needed some help calibrating my projector.  So I made the mistake of going up on CraigsList and found someone that seemed fairly experienced and asked him to come out to my house.  Now setting up a projector is not something easy to do, so before agreeing to this, I asked him a myriad of questions over the phone, all of which he seemed to answer with acceptable answers.  A few hours later, he showed up, and I was immediately taken back by his appearance.  He was disheveled and had an odor of 5-day-old fish. 

My Dad taught me never to judge a book by its cover, so I reluctantly allowed him into the house, where he quickly explained to me that my projector had to be mounted to my sofa?!?!  Dumbfounded, I told him I sat on my sofa; the projector had to be mounted to the ceiling.  He looked at me, confused. He was really stuck on this idea that the electronics would somehow balance on the seat of the sofa. I asked him very nicely to please leave, and he told me no and just glared at me. It was conflict, and for what I have no idea  At that point, I got nasty and told him in the not nicest possible way to get out of my house.  In a huff, he left. I have never allowed a person from CraigsList in my house again from that experience on.

To this day, I just scratch my head, wondering what he was really up to.

Eric, EZMoments

A few years back, I decided to Hitchhike across the country both ways

On the return trip, I got stuck in a small city in Texas, just about 2 hours outside of Big Bend National Park

Because of my situation of thumbing on the side of the road for nearly 4 hours, I decided to see if Craigslist could save my trip and get me out before nightfall

What ended up happening was a slew of email exchanges between a couple of swingers who didn’t make it clear until after I agreed to a ride.

The only thing I didn’t tell them after they sent me photos of their “situation” was as I had someone pick me up before they were scheduled to get me.

Matthew Burke, Editorial Director, Complete Guide to Archery

I run a website called The Complete Guide to Archery, where I provide lessons, gear tips, and so on. As a side gig, I sell bows on eBay and craigslist. I’m not getting rich doing it, but it helps me pay off my student loans, and I’ve met some great people through it.

One time an older gentleman offered to buy a hunting bow from me, and because he couldn’t get around so well, I agreed to bring the bow to his house.

The moment I stepped in the door, I could tell something was… off. His house was a mess—there was food everywhere, the place smelled really bad, and he was talking a mile a minute. He kept talking about something called “The Main Event,” and he was really concerned about it.

After politely asking a few questions, it turns out he was stockpiling bows for the upcoming apocalypse. “The Main Event” would be our final battle against our robot oppressors, and he just wanted to be ready.

I left, presto-pronto, and took the bow with me.

I felt bad for him, so I checked in a social worker friend of mine, and it turns out he knew the guy—the guy had some mental health issues and had lapsed on this medication. Such a strange occurrence—I’m just grateful things turned out the way they did!

Michael James Nuells

So, 2 friends pitched Craigslist to me as a social networking platform and suggested that I use it to find “new friends” and “colleagues” for my YouTube channel. After joining, I luckily stumbled across a listing by a gentleman who was seeking the same thing as ME! I contacted him immediately, he responded instantly, and soon after, we exchanged contact information and photos and planned to meet to discuss our YouTube endeavors.

Regrettably, I agreed to meet at his home so he could show me his available equipment to use for our videos. Once inside, he immediately led me upstairs to his “office”, where I found 2 half-dressed men. Initially shocked, he insisted they were friends who had crew experience that he invited over to help discuss logistics. At that point, I just said OK & carried on checking out the equipment. Roughly 15 minutes into our conversations, they segued into stories about being PORNSTARS! They directly asked me to join them, assuring that the 4 of us would make tons of money together making videos. Traumatized, I realized that I had been set up & needed to get out ASAP! I told them I needed time to decide since I didn`t come prepared. They said they understood & would contact me back soon since they had my contact information. Moments later, we walked downstairs and said our awkward goodbyes; I ran to my car and sped away! While driving, I blocked ALL of his contact information, LOL!

Ethan Taub, Goalry

I was in my early twenties, and my mum and dad had bought a new oven; I took the old one as it was better than the one I had.

I put the ad up on craigslist for $50 and got my friend to help me carry it out into the front yard.

I got a phone call within the hour with a lady saying she had been looking for an oven for weeks, she said she’ll be over to pick it up with her husband when he gets home from work. 

I look out the window about 20 minutes later to see that the oven has gone, somebody has only gone and stolen it. I rang the lady to tell her about the stolen oven, but she didn’t answer.

I tried her a few times to no avail but eventually got a call back off her, and she sounded very sheepish. She told me she didn’t know how to say this, but her husband had come home from work with an oven in his van that he had ‘found on the street’.

She recognized immediately that it was my oven, and they had a massive argument over it.  She promised to wire me the money immediately if I didn’t report it to the Police. I agreed and got the money within the hour. Karma, I guess.

Elliot Reimers, Certified Nutrition Coach at Rave Reviews

I bought a large, ornamental decorative vase from Craiglist, and helpfully the guy said he would deliver it for free.

He seemed to be in a rush, so I had a quick check-over of the Vase and paid him so he could be on his way.

About an hour later, I heard a hissing coming from the vase; I glanced over from the TV, and a freaking snake was crawling out of the Vase!

Oh yeah, the vase was Opaque, obviously.

I ran out of the house and called Pet Rescue for help. They came out and removed the snake, laughing as they told me it was ‘only’ a corn snake!

So as it turns out, this cheap Vase was just a ruse to get rid of a snake, as the guy never answered any follow-up calls from me!

Andrew Roderick, CEO of Credit Repair Companies

After a year of deliberation, I finally listed my ex-girlfriend’s engagement ring on Craiglist.

Had a guy come over the very next day and buy it off me for $2000 dollars, and I congratulated him and wished him the best of luck.

Less than a week later, I had a text demanding a refund as his girlfriend had said no. I said that’s not how it works, sorry.

Within 30 minutes, he had come around again and was banging on my front door, shouting for his money back. I called the cops, who calmed him down and helpfully suggest he should try and sell it on Craiglist too.

Amber Adams, Founder of Kitchens Ready

My hands-down favorite experience that I’ve had on Craigslist is that people are willing to manual labor for you in the name of free things!  I’ve found that you can post a ton of things in the “free” section on Craigslist that you might think are trash but are a treasure for another person.  But the below experience is, by far, my favorite!

One spring, my husband and I were having a large project completed in our backyard.  We need a ton of landscaping rock, and some various plants and bushes moved out of our yard because we were having a huge outdoor living area put in.  The contractor that was designing our backyard living area would have charged for labor to remove or move the rock and bushes.  As we all know, landscaping rock and plants are pretty pricey when you buy them new from a hardware store or nursery.  We posted our outdoor items in the “free” section on Craigslist, thinking it might be a while before we snagged the right person.  Within the hour, we had people begging for our address to come to take the rock and plants!  It was gone from our yard within a few hours, and we didn’t have to pay our contractor labor to remove it for us.  We would have loved to use the rock elsewhere in our yard, but we just didn’t have the right spot, so it worked out well.  Win, win!

Brett Downes, HARO Helpers

When I traveled to Australia, I planned on living in Sydney for a few months, which meant I needed to get a job as it is super expensive.

I decided to set up a beach sunbed application service and had to advertise for sunbed girls on gumtree and craigslist. It’s the craigslist replies that astounded me.

The emails had to send a photo of them, face only, along with a brief as to why they would be a good fit for the role. The replies I got were verging on soft porn, with images to match!

I quickly edited the ad and added Face photos only at the start and end of the ad to stop any more raunchy photos from coming through.

Not quite the end of the story, I was also a dog babysitter for a dog that had recently had a stroke. I turned up one day to look after the dog while the owner went to work; she was a nurse. Upon checking my emails, I saw new applications, one of which was her in only her lingerie. I was horrified and amused in equal measure; suffice to say, I never mentioned it to her for the next 2 months I was working for her. 

Michael Lowe, CEO of Car Passionate

I saw a yoga mat super cheap on Craiglist and drove over to this guy’s house to pick it up. He seemed like a nice guy, and we were chatting about how fitness equipment is in demand during social distancing, and I couldn’t find dumbbells as all sites were out of stock.

I was browsing Craiglist a few days later and saw that there were dumbbells for sale – the exact ones I wanted – from the same guy! I did think it was a tad weird that he hadn’t mentioned it before.

Again, I drove over and picked up the dumbbells, but they were brand new. I asked why is he selling brand new ones, and he told me he had bought them for me as he knew a guy from his gym who could get them! I considered this for a second, made my excuses, and left very quickly.

Let’s just say I was happy I was the buyer and not the seller, else this guy would know my address!

Paige Arnof-Fenn, Founder & CEO of Mavens & Moguls

When I bought my first home in 2006, there was an old washer & dryer in the basement, so I decided to buy a new one and sell the old one on Craigslist.  The first guy who responded sounded nice & his dad’s machine had just died, so he said he’d come over the next day.  

The guy was a firefighter from a neighboring town and told me he would not leave until I knew basic things about my new house, like how to shut off the gas, etc. He spent an hour going through it all with me, and in the end, I refused to let him pay me because he gave me such a great education on home ownership.  We both thought we got a great deal!

Dan Bailey, President of WikiLawn

I actually spent some time in the mid-2000s looking for cars on Craigslist. I thought I could get a better deal than even the used dealerships here, which is technically true. But I had to wade through so many terrible ads and scams, with cars that very clearly weren’t as advertised. 

There’s one that takes the cake, though. I was looking at a 2005 Honda Civic. Pretty good condition. The seller took lots of pictures — exterior, interior, under the hood, etc. I could very clearly see the minor body damage and a couple of other issues that would be fairly cheap to repair. 

It was a good deal. Nothing outrageous, but enough to get me out there. I went, and test drove the car. Inspected it. Everything looked good, and I was prepared to negotiate with him on price. He started being really evasive at that point, not wanting to settle for any of my negotiations. 

He explained that it was his wife’s car and she didn’t really want to sell it, but he had some cars I might like. I was baffled as to why he’d advertise a car he didn’t want to sell but agreed to look at the others. Parked behind his property were a variety of newer cars that looked like they’d been driven right off the lot. Warning bells went off immediately, especially when he told me the prices, which were far below what the dealerships would sell these cars for.

Needless to say, I made my excuses and left quickly. I have no idea if he was running some illegal operation or not, but I had no interest in sticking around to find out. 

Robert Barrows, Barrows Advertising & Public Relations

I do some sculpture, and I ran an ad for one of my pieces on Craigslist. The price of the piece was $7,500.00. I had seen some stories on TV about scams where people paid you thousands more than you were asking, hoping you would be foolish enough to send them a refund. I received some odd email inquiries from a person about my art. I knew it was a phony from the early emails I got.

The initial emails I received were full of misspellings and incorrect grammar, and they didn’t even have any contact information. If it were a serious inquiry about the piece of art I was selling, the potential buyer would have been more detailed. At one point, they asked for my bank account number so they could wire the money into my account. I never gave them that number. I also asked the person to give me his shipping address because If he lived in California, I would have to charge him sales tax.

I never received any reply, but about two weeks later, I received a FedEx envelope, and the only thing that was in it was a check for $17,500 ($10,000 more than the item cost). There wasn’t even any letter enclosed with the check, and the check itself was obviously fake. On the check, the word Boulevard was spelled wrong, and they also spelled the word Manhattan (as in Chase Manhattan) incorrectly. So, instead of taking it to the police, I just took the check to my bank and told them it was fake; the bank said they would send it to their fraud unit.

Nikki Webster, Brit on the Move

I once ordered an excessive amount of Retina-A cream by accident – more than I could use. I listed the excess on Craigslist. I did not know at the time that you can’t list a prescribed product or a product that is prescribed in the US. I had one listing, and one person wrote to me and told me that I can’t list the item, and I took it down.

What followed was nothing short of harassment. This person emailed me daily, saying I needed to take my listing down. I told them time and time again the listing has removed the instant they educated me. It did not stop, and I got the sense that there were other listings that they assumed were me. I had to research this person’s IP addresses and then threaten them with a visit from the police. Naturally, it stopped there and then. However, it was a really strange encounter.




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Chad is the co-founder of Unfinished Man, a leading men's lifestyle site. He provides straightforward advice on fashion, tech, and relationships based on his own experiences and product tests. Chad's relaxed flair makes him the site's accessible expert for savvy young professionals seeking trustworthy recommendations on living well.

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