The Most Swoon-worthy Love Letters of All Time

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There’s no denying it: Love is in the air. And while romance often takes center stage this time of the year, Valentine’s Day is the perfect occasion to celebrate all kinds of relationships and make sure everyone we love feels it. Roses and chocolates are nice, but sometimes, the best way to tell someone you love them is by, well, telling them! With social media and smartphones, we reach many of our loved ones instantly. But that convenience often comes at the cost of a more deliberate and lasting sort of communication. It’s high time we brought back the lost art of the love letter—or rather, reminded ourselves that the art was never really lost.

True, it’s not often that we sit down, pull out the fountain pen, spritz some perfume on a scroll, and start dashing off curlicued missives to our dearly beloved, but we are still finding ways to put our hearts on the page. Some may take a more conventional approach (see: John Legend’s tear-jerking letter to his wife of over a decade, Chrissy Teigen, on the way their relationship has changed with the years), while others have added their own modern spin to the classic form (see: Lizzo, natch). Read on—and write your own.

1. Best letters of feverish young love

Before he was an American president, a bestselling author, a Time magazine Person of the Year, and (perhaps most impressively) the husband of Michelle, Barack Obama was a gawky young college student—and he was smitten. In the series of letters he wrote to his then-girlfriend Alexandra McNear between 1982 to 1984, we see a side of the former president that didn’t make it into Dreams from My Father or onto the campaign podiums: a side that is self-conscious (referring to himself as “a blathering chump”) and, at some points, downright corny (“My concern for you is as wide as the air, my confidence in you as deep as the sea, my love rich and plentiful”). It’s nice to know that even the greatest minds can go mushy under the weight of young love!

A line you should steal: I trust the strength of our relationship enough that I can show myself with curlers in my hair, my will sapped, my confidence shaken, a bit peevish perhaps, a bit dull.

2. Best letter of enduring love

“I don’t love you like I used to” doesn’t seem like the best way to start out a love letter to your wife of more than 10 years. Indeed, the sentence certainly made Chrissy Teigen raise an eyebrow when she read it on the track list for his album Legend. But in the intimate missive that kicks off the heart-stopping 2023 anthology Black Love Letters, John Legend makes it clear that it’s a good thing for love to change. To the then-pregnant Teigen, he writes, “I needed to tell you how proud I am of how we’ve grown together, how we’ve challenged and taught each other, how our love has evolved into something we never could have imagined when we first met. I don’t love you like I used to.” Too often, we idealize the early days of love with all the palm-sweating and butterflies and anxiety and high drama. Here Legend makes the perfect case for the slow burn: a love that includes household chores, Real Housewives, earth-shattering loss, mutual respect, and—thankfully— a whole lot of change. May we all be so lucky!

A line you should steal: If ever I am strong for you, it’s because I’ve witnessed the strength you already have inside yourself…. Like life, your spirit is persistent.

3. Best letters of brotherly love

You don’t have to be an art historian to know that Vincent van Gogh, painter of The Starry Night, had some serious demons—but he also had a brother, Theo, who loved him: fiercely, unconditionally, and unpityingly. That love is captured, achingly, in the brothers’ near-constant written correspondence; of the 820 letters by Vincent collected in Amsterdam’s Van Gogh Museum, 651 are addressed to Theo.

Today recognized as one of the most brilliant painters of all time, Vincent van Gogh spent his life in poverty and obscurity; he famously severed his own ear, spent years of his life in mental institutions, and died—likely by suicide—at the age of 37. In the eyes of Theo van Gogh, however, Vincent was always a genius. More than that, he was an older brother, and Theo looked up to Vincent, throughout his struggles, with the unabashed pride and admiration familiar to all younger siblings. On the day that his only child was born, Theo writes to tell his brother that he named him Vincent with the “wish that he may be as determined and as courageous as you.”

The world would never know and love Vincent van Gogh if Vincent van Gogh did not know and love Theo, who encouraged his brother to become a painter, tirelessly promoted his work, and offered financial and emotional support to the artist throughout his life. Though Vincent expresses guilt, many times, for his reliance on his younger brother, Theo won’t hear of it: “You’ve given it back to me several times over, both by your work and by a brotherly affection which is worth more than all the money I’ll ever possess.”

A line you should steal: May our love for one another only increase as we get older. I’m so happy that we have so much in common.

4. Best letters of writerly love

If you are looking for a cute, low-stakes way to let your special someone know you are thinking of them, consider taking a page out of the novelist Vita Sackville-West’s book. “I am reduced to a thing that wants Virginia,” Sackville-West wrote to Virginia Woolf in 1926 while vacationing in Milan, the first separation the lovers had endured since their all-consuming affair began. Five years before Sackville-West penned that panting missive, lawmakers voted to criminalize sexual acts "of gross indecency” between women (male homosexuality was already criminalized in Britain), but it never became law out of fear that it might advertise the possibility of same-sex exploration to delicate ladies—as we certainly could never have dreamed of the idea on our own! This failure of the male imagination left Sackville-West and Woolf—both of whom were married to men throughout their affair—in a convenient gray area as lesbian lovers, a position they exploited luxuriantly. Both writers and poets, many of their exchanges are gorgeously lyrical and pulse-quickeningly touching (from Woolf: “Yes yes yes I do like you. I am afraid to write the stronger word”), but a few are downright steamy. Take, for example, Sackville-West’s cheeky line “I regret that you have been in bed, though not with me.” If that’s not the 1930s equivalent of a sext, we don’t know what is.

A line you should steal: You have no idea how stand-offish I can be with people I don’t love. I have brought it to a fine art. But you have broken down my defences. And I don’t really resent it....

5. Best self-love letter

We all know we need to prioritize “self-love,” but what exactly does that look like? If we’re not careful, it can end up looking like a chore—something approaching a New Year’s resolution to eat more kale. Lizzo’s 2019 ballad “Soulmate” reminds us that self-love is not about optimization or hollow affirmations but about romance, with all its indulgence, care, and (yes!) great sex. Self-love means “flowers every Sunday,” wining and dining yourself, and knowing, when you look in the mirror, just how lucky you are to be able to say, “Damn, she’s the one.”

A line you should steal: I’m my own soulmate/I know how to love me/I know that I’m always gonna hold me down.

There’s no denying it: love is in the air. And while romance often takes center stage this time of the year, Valentine’s Day is the perfect occasion to celebrate all kinds of relationships and make sure that everyone we love feels it. Roses and chocolates are nice, but sometimes, the best way to tell someone you love them is by, well, telling them! With social media and smartphones, we reach many of our loved ones instantly. But that convenience often comes at the cost of a more deliberate and lasting sort of communication. It’s high time we brought back the lost art of the love letter—or rather, reminded ourselves that the art was never really lost.

True, it's not often that we sit down, pull out the fountain pen, spritz some perfume on a scroll, and start dashing off curlicued missives to our dearly beloved, but we are still finding ways to put our hearts on the page. Some may take a more conventional approach (see: John Legend’s tear-jerking letter to his wife of over a decade, Chrissy Teigen, on the way their relationship has changed with the years) while others have added their own modern spin to the classic form (see: Lizzo, natch). Read on—and write your own.

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