Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration,

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I sell fitness equipment to gyms. Last year, I was close to landing an account with a former pro bodybuilder who was opening his second location. After several promising meetings, he invited me to meet him at his flagship gym to "finalize details." When I arrived, he was just finishing a workout. I started discussing equipment specs, but he cut me off and suggested we go in the sauna. He joked that “that's where the deals happen."

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I'd only been in a sauna a few times in my life, but I wanted to get the deal done. I changed in the locker room and met him in there wearing some workout shorts. It was extremely hot at first, but I got in the zone as we chatted about financing terms, warranties, and maintenance schedules. After about 15 minutes or so, I started to feel lightheaded. The next thing I remember, the guy was pouring water on my head and shaking me. He said I had passed out for about 30 seconds and he had helped me out of the sauna and into the locker room like I was an injured football player. He laid me down on a bench and elevated my legs with some towels and gave me two big cups of water. I laid there for about 10 minutes before I had the strength to get up and get changed. Afterwards, I met him back in the gym, apologized for the fuss and thanked him. He laughed and said he thought for a minute there he was going to have to dispose of a body.

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I called him the next day and he informed me he was going with another vendor that he thought was a better fit. He didn't give me much more information than that. I'm fairly certain it's because he thought I was weak because I couldn't last 20 minutes in the sauna.

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Anonymous       Location withheld   

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I sell software—my region is in the Midwest. One of my best customers was a guy I had bonded with over our shared team (the Detroit Lions). Our calls always started with sports talk before business. During a routine check-in last fall, he mentioned he'd started using a betting app. Coincidentally, I'd been on a hot streak with my weekend picks. When he complained about losing three weekends straight, I casually suggested a pick that I felt was a lock. The next week, he called about a contract issue but started by thanking me—he'd won $200.

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Feeling like a genius, I shared my "lock of the week" with him. When that hit too, our relationship shifted. He'd text asking, "Got anything good this weekend?" This went on for a few more weeks, and he kept hitting. Until my hot streak finally ended. What I didn't realize was that my casual picks had become gospel to him. 

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Monday morning, I got an angry call. He'd bet $2,500 and lost everything. He threatened to cancel our contract and even mentioned (this was in the heat of the moment) speaking to his company's legal team about my "gambling advice." He eventually calmed down but our relationship was destroyed overnight. He still buys from us, but routes everything through his assistant. Not great. 

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Anonymous       Location withheld   

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I used to sell funeral services. I only lasted about a year, and it was a pretty depressing job. One day I was showing casket options to this family who had just lost their elderly mother. Overall, they seemed to be handling the whole situation well, as people crying in the showroom was not an unusual occurrence.

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After about 30 minutes, they had decided on a nice mid-range mahogany model. I was told that whenever customers picked anything mid-range or above, it was an opportunity to upsell them. I started showing them upgrades and pitched them a premium silk interior package. Trying to keep the mood light, I said "Your mother will be spending a lot of time in this, so comfort is key." I don’t know why I said this—I think I was in a pretty good mood that day. 

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Complete silence. After a moment, the son looked me dead in the eyes and said "Do you really think this is a good time to be making jokes?" I apologized profusely. The son accepted the apology and told me it was fine but I could tell he was upset. He told me they'd take the silk interior package and handed me his credit card and said, "Just let me pay so we can get out of here." I got the sale and he walked out, but that was the last time I ever tried to make a joke at that job.

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Anonymous       Location withheld