Letter Bomb

Breaking up is hard to do right. Especially on paper.

Book cover

What makes a great breakup letter? As is the case with so many hypothetical questions you never thought about before, there is a new book that thinks it has the answer. In Hell Hath No Fury: Women’s Letters From the End of the Affair, editor Anna Holmes presents a compendium of eight centuries’ worth of breakup missives by both historical figures (Anne Boleyn, Mary Wollstonecraft, Edith Wharton) and everyday women (plus the requisite number of Sex and the City writers). The book is a godsend—but probably not for the reasons Holmes originally intended.

As literary anthologies go, Hell Hath No Fury is pretty heavy sledding. In too many of the thematic chapters—the Tell Off, the Unsent Letter, the Goodbye, and so on—readers slog through boring or tangential historical documents, followed by excruciatingly banal modern-day writing. (Take Kim, 27: “I realize that I didn’t do a good job of giving you space this week. I was so bewildered by your not calling. … You seemed so sincere when you were telling me all about your childhood and the issues around your father’s death.” This after two dates with a man she met on But as a how-to—or rather, how-not-to—manual, the book is downright indispensable. After all, there’s nothing like watching Sylvia Plath and Simone de Beauvoir fail to write truly great breakup letters to convince you not to try in the first place. Here’s why:

1.The odds of succeeding are bleak. Reading Hell Hath No Fury, it quickly becomes clear that there are an almost unlimited number of ways a breakup letter can fail. Self-pity, stridency, pettiness, arrogance, appalling grammar—the beach is littered with all sorts of sharp rocks that can puncture a letter before it even pushes off. In contrast, the epistles that still leap off the page and grab you by the throat (even decades or centuries later) share just one common attribute: There is a little kernel of something in each great letter— be it eloquence or dignity or grief or humor—that you can imagine made the recipient think, “I’ve made a terrible mistake.” (Typing these words, I can almost hear a chorus of women’s voices chanting, “I didn’t write it for him, I wrote it for meeeee,” but the fact remains that not one of the letters included in Hell Hath No Fury begins “Dear Self.”) Now for the bad news: Of the 149 letters included in this collection, by my estimation there were only nine that unequivocally contained that kernel of greatness. Nine. That’s a failure rate of 94 percent.

2.You can’t rewrite history, not even with the backspace key at your disposal. What a nice idea to think you could somehow shift the balance of power in a relationship with one last letter; what a shame that this is apparently impossible. Too many of the modern-day Clarissas in Hell Hath No Fury got themselves into demeaning relationships with jerks, then composed breakup letters as futile, last-ditch attempts to get their swains’ reprehensible behavior on the record. Take the missive by comedian/writer Lynn Harris that insists “… not calling me when I went home to my parents to PUT MY DOG TO SLEEP? … By the way, I broke up with you that weekend, the dog weekend. By myself. I just didn’t get around to telling you until you, you know, had a moment.” This is a pretty squirm-inducing read even with the self-deprecation; the book’s more pleading passages, like this one written by Australian artist Stella Bowen to Ford Madox Ford in 1928, are downright mortifying:

 … I think public opinion—for what it is worth—would be softened if we announce that our relations remain cordial, and if I might continue to know what you are writing, etc., and be able to give people some news of your career. … If it ever becomes known that we separated on account of R. I should like it also to be known that you wanted not to break with me outwardly, and that it was I who wished to end it all.

3.If you feel a pressing need to reach for the good stationery, you probably shouldn’t. In one of life’s annoying little ironies, like starlets being able to borrow Harry Winston jewelry, the best breakup letters are penned by the women who least need to write them. In other words, those who have already moved on. Unlike the frantic revisionism above, the most affecting writing is all anchored by a certain dignified inevitability. When TV producer Cindy Chupack clarifies her unreciprocated feelings for a friend, she’s clearly given up on winning his heart:

So … if you do just want to be friends, let’s just be friends and not do date-like stuff, because then I end up wanting to kiss you, and then you don’t, and then I just feel stupid, which is not helping me … meet other people who might actually want to kiss me and date me, which is something I rather enjoy.

Even Zelda’s letter to F. Scott Fitzgerald in which she writes “I love you anyway—even if there isn’t any me or any love or even any life—I love you” is devastating because of its naked acceptance that the good times are all gone. The best “it’s over” letters all have but one message—”it’s over.” Or, as novelist Kate Christensen puts it in the signoff to her elegant letter, “There’s so much more to say but I can’t say any more. Writing this letter about ending it with you is just another way to keep it all going, when what I need to do is sign off, and get out.” 

4.Do you really want to give him an excuse? Sometimes dignity is no object—and there are definitely letters in Hell Hath No Fury that are memorable for their sheer, unadulterated vituperation. That doesn’t necessarily mean you want to write one. In what is probably the book’s funniest entry, pseudonymous writer “Lola Fondue” delivers a 51-item list to an ex, beginning “1. You have B.O. even after you shower” and only getting meaner from there. Should her boyfriend “Ira” ever become a serial killer, this letter will no doubt be introduced in the insanity defense as Exhibit A. Reading Agnes von Kurowsky’s letter to Ernest Hemingway (“I know that I am still very fond of you, but, it is more as a mother than as a sweetheart”), all of his subsequent womanizing and misogyny suddenly seems more understandable, if not justified. The cruelest of all the letters in the anthology are the “Dear John” letters sent to servicemen—the literary equivalent of grenades. (“Honey if you ever intended to marry me I wished you could have done so before you left. … You see Harry darling I’m afraid it’s too late now—as I am already married.”) No wonder one GI mentioned in the book remembered another soldier standing up during a firefight and allowing himself to be shot after opening one of those. Even if the best your ex can manage in peacetime is stepping in front of a taxi, is that really the outcome you were looking for?

5.Once it’s out of your hands, a breakup letter has a life of its own. In case there’s anyone out there who still needs reminding: That e-mail in which you blame yourself for the “trouble” you two had in bed can be forwarded on to a thousand bond traders—or your parents. The letter detailing exactly how you’d like to mutilate his new girlfriend could resurface in the natural sequel to this anthology, ’Then She Just Wigged Out on Me, Man’: Letters Received From Women at the End of the Affair. Or, worst of all, pouring out your heart could result in the most chilling scenario of all—hinted at only once in Hell Hath No Fury, in this fictional breakup letter scene from Nabokov’s Mary:

[He] tore up each portion and threw the scraps to the wind. Gleaming, the paper snowflakes flew into the sunlit abyss. One fragment fluttered onto the windowsill, and on it Ganin read a few mangled linesourse, I can forg
ove, I only pra
hat you be hapHe flicked it off the windowsill into the yard smelling of coal and spring and wide-open spaces. Shrugging with relief, he started to tidy his room.