The One Email You Should Never, Ever Have Sent

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You know you've sent it: that angry, emotional or stingingly passive aggressive email to a friend/partner/parent/boss that gives them a piece of your mind. And chances are you've woken up the next morning in a haze of regret, wishing you could go back and hit un-send.

Although the general consensus from researchers is that electronically voicing our frustrations in the heat of the moment is a bad idea, that doesn't mean we're not still doing it. Mic recently asked 20-somethings to dish about that one email they truly regretted sending — and it turns out that nearly everyone has a story to tell.

Sending an email is a way to voice the frustrations you wouldn't IRL. Many of the emails we regret sending are sent to people in positions of power, like a landlord or a supervisor at work. "She would constantly change her mind and I would have to start over with little time," Kyle*, 22, told Mic of his boss' management style, which ultimately led him to send her an impassioned missive after he quit the gig. "I basically accused her of emotionally abusing me the whole time and being unreasonably impossible to work with." 

He also told her her work was "crap," which prompted her to fire off an equally aggressive reply. "The emails went on and on for two days. We were basically having an 'I'm right you're wrong' argument over all of this," he said. "It was just too much."

After all was said and done, only discomfort and awkwardness remained. "I deleted the emails due to my embarrassment," Kyle said. (Shockingly, he wasn't fired.)

Meanwhile, Robbie*, 27, most regrets an email he sent to the landlord of his first shitty New York City apartment. "There were roaches, they had a weird cat that I foolishly offered to take care of and the place was falling apart," he said. He found a new place after a month, and got very drunk before electronically sending his moving out notice. "I wrote something like, 'Vermin are unacceptable in any living space,'" he told Mic. "And then, 'Fuck you and fuck your dilapidated shit-hole of an apartment. I'M OUT! P.S. your cat is gross.'"

Martin*, 26, sent an impassioned email to his psych professor after he accused him of cheating on a take-home quiz. "I [actually] cheated," Martin said. "He was totally in the right. But it didn't stop me from getting extremely defensive."

Source: Mic/Getty Images
Source: Mic/Getty Images

Email my heart: When emotional emails mix with our romantic entanglements, the results can be even more cringeworthy. Selena*, 26, said she once sent, "a 1500-word missive to an ex boyfriend I hadn't spoken to in months that he just never responded to. It was raw as fuck, and I'm shocked that we even manage to have a cordial relationship now."

Fifteen hundred words is no joke, but Margaret*, 23, had an even more epic tale to tell:

She once wrote a 10-page "prose-poem" for a class about a friend she had secretly hooked up with once who subsequently ghosted her when his ex-girlfriend found out. While there was never any intention to show it to him, when alcohol got involved one night, she couldn't help herself. "I wrote him an email being like, 'You treated me like shit, you owe me an apology. And against my better judgment I'm attaching this story I wrote about us."

They ultimately decided not to be friends.

Source: Mic/Getty Images
Source: Mic/Getty Images

Us, uncensored: There are many reasons why psychologists advise us to cool off before hitting send on our email immortalized rants. Friendships, relationships and even jobs can be lost just because we wanted to blow off a little steam. This is not to mention the embarrassment that some who we talked to reported feeling after they went through with it. ("The shame and regret I felt the next morning wasn't worth it," said Robbie.) In fact, research shows that sending angry emails only succeeds in making us angrier.

While it's true that letting our raw, unedited feelings show in Gmail may not always be the most productive choice if we're looking for some form of resolution, there's also value in sending an angry email purely as a means of validating our feelings, however irrational or over the top they may be. After all, as a 2013 study reported, bottling up our negative emotions can actually be harmful for our health.

Maybe angry emails are one of the few places in which we can actually set our spirits free — in long form, with the luxury of multiple rounds of edits, spell checks and dramatic out-loud practice readings to really bring the argument home — without worrying about how "appropriate" our emotions are.

While it's probably never a good idea to sweep our anger entirely under the rug, there are also more productive ways of expressing it than type-screaming "FUCK YOU!" at an ex-landlord. But man, does it feel good to press "send."

*Names have been changed so subjects can speak freely on private matters.