Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).
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“When I first got into sales, I had no idea what I was doing. I was in my early 20’s, and I was a retail cell phone rep at a big electronics chain. I was eager to do well, so I made sure to listen to advice from my new managers and coworkers. One of the things my supervisor at the time said was to always try to relate to the customer, no matter what they were talking about. He was a super smooth guy who could charm anyone, and I’d watched him in action and was always impressed with how well he controlled the conversation. 
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During my second or third month on the job, this friendly guy came in looking for a family phone package for his wife and kids. From what I remember, he was an engineer, or did something that had to do with computers. So we were talking and I was showing him our phones, and somehow we got on the topic of Star Wars, and I reflexively said that I loved Star Wars even though I’d never watched a single one of them in my life. 
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All of a sudden, his eyes light up, and he starts talking about the movies in detail, and I’m nodding along and smiling, figuring this was going well. Then, he starts asking me about what I like. And at first I was able to play it off, but then he starts digging a bit, and I say “Oh, it’s been so long since I’ve seen them,” just trying to get him off my case. But he refuses to change the topic, and starts getting serious with his questions, and I’m super awkward by this point, stuttering over my words. Finally, he lets me off the hook and goes back to asking questions about the phones, but by that point, he wasn’t friendly at all anymore. 
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He thanked me and said he’d come back if he had any more questions and left without buying anything. To be honest, I was glad to be rid of him. I’m still in sales, but I make it a point to never, ever pretend I know something that I really don’t know. Oh, and I’ve still never seen Star Wars” 
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Anonymous, 30    Colorado 
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"I was working for a medium-sized software company a few years back, and we were pitching another medium-sized company in person. My sales engineer was running late, but while we were waiting, I joined the four prospects in the conference room. They were joking around and talking about milking cows in Vermont, and I thought we had a good rapport, so I said that line from the movie Meet the Parents: 'I have nipples Greg. Can you milk me?' I have no clue why I said it but as soon as it came out, everybody just went silent. Needless to say, the rest of the presentation was super awkward, and my poor sales engineer was probably wondering why there was so much tension, but we actually ended up closing the deal, and they kept it professional even though I was super embarrassed."
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Anonymous, 37  Phoenix, AZ
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“I’m not sure if this is an actual Sales Fail, because it wasn’t my customer, but back in 2006, I was working in the mortgage industry, and a woman I worked with was doing a refinance for this guy. Everything was over the phone, so she’d never met him in person. 
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Anyway, one day, she needed him to sign some documents, and it was very time-sensitive, so we didn’t have time to FedEx them to him and wait for him to send them back (back then, we were using fax more often than electronic signatures etc.). The guy lived about twenty-five minutes from our office, but she didn’t feel comfortable going there, because he would make inappropriate comments to her over the phone and ask her about her personal life and whether she was single. Anyway, the manager decided it would be safer to send one of the guys over there, and I was still relatively new and didn’t mind getting out of the office for a bit, so I volunteered to go, and the woman actually let me take her brand new BMW to make the drive. 
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“So I pull up to the house, and it’s a pretty run down ranch on a side road, but nothing too horrendous. When I get to the door, I hear classic rock blasting at basically full volume. Eventually, the guy comes to the door, his eyes are totally glassy and bloodshot red, and he invites me in and offers me a beer (which I declined). So we go to the couch and I give him the documents to sign and he lays them out on the table. The music is blasting, there are empty beer bottles everywhere, and I see what looks like white powder residue on the coffee table. 
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“This guy can barely pay attention as I show him where to sign, and keeps trying to get me to talk about my female coworker instead. I look over, and see a black handgun on the side table next to him and start looking for the back door, in case I need to make an escape. I was truly getting myself mentally ready to have to fight for my life, when the guy looked at me, dead serious, and said, “Why are your pupils so big dude?” Then there was just this tension-filled silence for what felt like an eternity before he burst out laughing, which quickly devolved into a coughing fit. Then he sees me looking at the gun and offers to let me hold it, but thankfully doesn’t pick it up. Finally, I convince him that I’m in a hurry and get him to sign the paperwork. 
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“After that, I got out of there as quickly as possible, and, from what I understand, he ended up completing his refinance without any further issues. I got out of the industry less than six months later, but I’ll never forget going to that house.”  
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Anonymous, 38