Breakups are tough. They're rife with unanswered questions, with things unsaid. Except when things are said. Enter the breakup email.
"Some are like autopsies," said Anna Holmes, founder of Jezebel and editor of an anthology of famous break-up letters from women titled Hell Hath No Fury.
Holmes explained that these kiss-offs come in all shapes and sizes. Sometimes the writer is looking to determine the cause of death of the relationship, or using the email as a form of catharsis and therapy. Other varieties include the "I want you back" missive and the self-aggrandizing "Here's what's wrong with you and what's right with me" letter.
"Whatever feeling you can possibly feel at the end of the relationship can be reflected in these letters," she said.
That means break-up emails are often filled with raw, uncensored emotions and often sent off into that black hole known as the Internet, where a single sentence lives forever.
Recently, an unfortunate OKCupid user sent a long and critical email to a girl he'd been on just three dates with explaining why the two wouldn't be seeing each other anymore. His e-mail ended up on Gawker.
"You have to assume when you're writing this sort of thing that 10,000 people are going to see it," Holmes said. "Once you send it there's no going back."
So if you must put your feelings into words -- and it's okay if you must -- think carefully before you put them into an email, and even more carefully before you send. Holmes suggested having a trusted friend look over your letter first.
Otherwise it might end up here, cataloged in our slideshow of horrible breakup emails that got away:
After just three dates, this OkCupid user made a laundry list of reasons why he no longer wanted to see his online match, even suggesting that she move to the other side of the country, where he thought she'd fit in better. Gawker dubbed him the creator of what "may be the most annoying online dating break-up letter ever." Read the full text here.
Possibly the first preemptive break-up letter to gain internet fame came from one Bryan Winter, who supposedly contacted the recipient after meeting her out dancing. She is said to have replied asking for some basic information about him, such as his last name. His over-the-top reply, which you can read in its entirety here, made its way around the web and caused such a stir that it was covered in the Washington Post (which tried and failed to track him down).
Jezebel's collection of "Crap Emails From A Dude" includes this gem from a guy who'd been seeing a woman for two months before breaking up with her. In his Dear Jane email, he decided to flaunt the sexual escapades he'd had with other women while dating her. Read his full email here.
The purple prose of this "I want you back email" ended up in the hands of the intended recipient's husband. Don't miss the full original Facebook message, and the husband's priceless reply.