4 of the most romantic love letters to be sold at auction

Here at H&T, we’ve seen a number weird and wonderful items, from Fabergé eggs to livestock. But one of the most fascinating pieces of memorabilia we’ve seen so far has to be a letter written by Princess Diana, less than a month before her tragic passing.

When deciding on items to pawn, many people don’t consider this type of memorabilia, but letters have the potential to be incredibly valuable. In fact, if the piece is written by an important figure, or has particularly interesting content, it may even be able to fetch six figures at an auction. And when it comes to captivating content, nothing is better than a love letter. To celebrate Valentine’s Day, we’ve rounded up four of the most romantic and valuable love letters to be sold at auction, which should give you plenty of inspiration to pen your own love letter for February 14th.

Tupac Shakur

In 2020, a selection of love letters written by the iconic American rapper were sold at Sotheby’s dedicated Hip Hop auction. The recipient of the 22 letters was Tupac’s high school sweetheart, Kathy Loy. Tupac was just 16 when he wrote the majority of the letters, which gives us a glimpse of his life before he became the legendary rapper we all know today.

The 22 letters span the length of their young love, from their first meeting to over a year after their break up. His talent can be seen throughout the notes, even at such a young age. He wrote in a lyrical style in a number of sections, with one of the letters reading, “I love you now more than ever, want you now more than before, No one compares to you, the one that I adore.”

The letters give us a true insight into his character, showing him to be a sensitive teenager who experienced insecurity just like the rest of us. In one note he even admits that he considered giving up rapping before he made it big. These letters are truly touching, so it’s no surprise that they managed to sell for an impressive $75,600 (£55,558.06).

Joe DiMaggio

This American baseball star’s love letters weren’t just deemed as valuable because he was the author. The recipient was another 20th century American idol: Marilyn Monroe. After finding out that Monroe wanted a divorce, DiMaggio wrote, “I can tell you I love you seriously, way deep in my heart, irregardless of anything.” This letter alone sold for a staggering $78,125 (£57,413.67).

This wasn’t the only of Monroe’s letters sold at auction either. A note she penned to her third husband, Arthur Miller, was sold for $43,750 (£32,151.66) at the same auction. Other mementos of the American icon auctioned off at the same time include a silk overcoat, a bra, and a black beaded necklace.

Frida Kahlo

Frida Kahlo is one of the most renowned artists of the 20th century, and it’s easy to see why. Her variety of self-portraits are considered by the art world to be fantastic forms of self-expression. But Kahlo didn’t just express herself through painting. Her love letters to Spanish artist and writer José Bartoli show the Mexican national treasure had a way with words too.

The notes included a great selection of poetic and romantic lines like, “since I fell in love with you everything is transformed and is full of beauty… love is like an aroma, like a current, like rain.” The collection of letters spanned over 100 pages, and included other mementos, such as photographs and drawings. They were put up for auction by Bartoli’s family and sold for a grand total of $137,000 (£100,680.61).

Leonard Cohen

Any Leonard Cohen fan knows just how romantic, yet heart-breaking, his lyrics can be. And his love letters are no exception. He penned a number of romantic notes to his muse and former girlfriend, Marianne Ihlen, which were sold at auction for $876,000 (£644,127.18).

She was Cohen’s inspiration for a number of his most popular songs, including “So Long, Marianne”, in which he even references the letters they sent one another. Among the letters are poems which many have deemed to be drafts of lyrics used in some of his music.

The pair kept in touch until the very end, with Cohen’s writing to her shortly before her death in 2016: “And you know that I’ve always loved you for your beauty and your wisdom, but I don’t need to say anything more about that because you know all about that… Endless love, see you down the road.”

If you’re looking to make a romantic gesture to your special someone this Valentine’s Day, hopefully the letters above give you some inspiration. Looking for a meaningful gift to go alongside your love letter? Make sure to check out the selection of men’s and women’s jewellery here at H&T, including rings, necklaces,earrings, and more.

Opting for a romantic getaway instead? Be prepared by getting your travel money at H&T beforehand for the best rates.

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