These are the emails you regret sending

Ever pressed ‘send’ only to realise you’ve sent an email to the wrong person? Or fired off a ranty text after a few wines that you'll regret the next morning? At least you're not alone, read on...

This month, Netflix drops new film Desperados, a comedy hooked on hopeless romantic ‘Wes’ (Nasim Pedrad) who heads to Mexico to delete a drunk email she sent her boyfriend, before he can read it. While most of us haven’t travelled quite that far, it’s something many of us can relate to (right? Right?!). Here are the biggest clangers you (anonymously) told us about...

Wrong number

“When this guy kept asking me out, I told him I was dating a male friend in secret (who I was absolutely not dating). Only I accidentally sent the text to the friend, by accident. The chap who kept asking me out had the personality of a prawn and so my plan was to let him down gently. My male friend was very, very confused but understood thankfully. He actually came out about six months later, which probably explained why he was so understanding about it…”

Selfie shame

“I once sent a pouting selfie of myself as an attachment to a job application, clicking the wrong image on my laptop’s desktop. The worst part is, I didn’t twig at all until the interview (which miraculously I was still invited to) when I saw the photo stapled to my CV. Looking back, I did think it was strange they asked me for my CV twice, but at the time I put it down to my prospective boss being disorganised. I didn’t get the job, but we did have a laugh about it in the interview, at least.”

Faking it

“Back in 2012 my sister and I were running a fashion and beauty blog. Back then, blogging was still fairly new so there wasn’t much detail about how to collaborate with brands and sponsored content. When we were approached by a digital marketing agency about including links within our posts for payment, we were pretty naive. So when an employee sent over an invoice to pay us via BACs, we - not knowing this was actually totally legit - were suspicious. So we contacted the company she worked for, saying somebody was sending dodgy emails and 'pretending to work for them'. They didn’t respond to that (I imagine questioning their authenticity irked them a little!) and we got paid thankfully. I still cringe about that now.”

Hen do horror

“A few years ago I was invited to my friend Amy*’s hen do, the details of which were all top secret from Amy. Only when I received the email, aghast at how expensive it was (we’re talking hundreds of pounds, which as a student I just couldn’t afford) I forwarded it to my cousin Anna*, to moan about it. Only of course, autofill meant I sent it to the bride instead. Not only was I slagging off her hen do (pretty awkward) but I’d also unwittingly told her all of the details, too. I didn’t end up going after that.”

Email evidence

“When I was working for a video streaming company overseeing international projects, I acted as communication between the sales reps and technicians. At that time, we employed a technician Mark*, whose days were numbered as complaints had been filed. He was working on a project for the Singapore office, whose Sales Rep, Eugene* was concerned about the delivery. Eugene voiced his concern to Mark, who didn't reply. The next morning, I found three emails in my Outlook inbox: the first was from Mark, asking how to recall Outlook emails. The second from Eugene, demanding to have Mark fired. And here’s the third: Mark was so upset about Eugene questioning his capabilities, he embarked on a racist rant about the Singaporean-born Sales Rep to me directly. But Mark hit the reply-all button, which included Eugene and his colleagues. Within minutes, I restricted Mark's access to the company and called for a disciplinary hearing. He was fired within 24 hours. I'm glad I had the authority to initiate immediate action, racism needs to be stopped.”

Sweet effort

“On my first day of work as a PA at a new company, my boss asked me to send an email round to the office (around 40 or so people) about a charity bake sale. Only every time I tried to send it, with myself in cc, nothing arrived. I must have tried ten times over the next hour, completely perplexed, before the office manager quietly came over and flagged that “perhaps everybody knew about the cake sale now”. To my horror, I realised I’d managed to organise my emails by ‘oldest first’ which meant I hadn’t spotted the (many, many) emails I’d been sending had sent just fine. To everybody. Multiple times.”