The Incredibly True Story Of The First-Ever Diamond Engagement Ring

How the iconic symbol for love really started.

Last updated on Oct 26, 2023

Man proposing to a woman Bmywuk | Zorana Djordjevic | VladGans | Getty Images 

When Sotheby's first announced the auction of a 24.78-carat fancy intense pink emerald-cut diamond with rounded corners, flanked by two shield-shaped white diamond side stones and set in platinum, in 2010, it was expected to sell for between $27 million to US $38 million.

Much to the auction house's delight, the ring, which had previously been sold to its former owner by jeweler Harry Winston in the 1950s, sold to diamond dealer Laurence Graff for $46 million, making it "the most expensive single jewel ever sold at auction at the time." Naturally, the lucky new owner named the magnificent beast the Graff Pink.


While we firmly believe that neither the size nor the price of an engagement ring has any bearing on the worth of a marriage proposal, the history of how we came to associate them with betrothals is undeniably fascinating.

Considering this got us thinking about some other interesting engagement rings and proposal stories, which, for better or for worse, have grabbed our attention in the past.

RELATED: The One Marriage Proposal Video You Need To See (Involving A Bus And A Robot)


Here is the true story of the first diamond engagement ring — plus 4 more weird and notable proposal stories:

1. The first diamond engagement ring was given to Mary of Burgundy by Archduke Maximilian of Austria in 1477

Legend has it that in 1477, Archduke Maximilian of Austria — the future Holy Roman Emperor Maximilian I — was the first man to present his beloved, Mary of Burgundy, with a diamond engagement ring (apparently at the advice of his court counsel).

"Maximilian," the story goes, "set off for Burgundy after arranging a proxy marriage. But he was an impoverished suitor, thanks to Austria's penchant for war. So, it is said, as he traveled through his native land, villagers pressed upon him gifts of gold and silver that enabled him to secure a diamond ring for Mary."

The gold ring, set with diamonds in the shape of a letter M, is currently housed in the Museum of Profane Treasury, part of the Museum of Fine Arts in Vienna.

The two remained married until Mary's death — which unfortunately came only five years later after she fell from her horse. She was just 25 at the time.


Despite their roots dating back to the 15th century as a symbol of life-long love, diamond engagement rings only became popular in the U.S. in the early 19th century.

They first began gracing the index fingers of American women in the 1910s and 1920s, when diamond rings came to serve as a sort of collateral meant to replace the protections women had previously been offered by "Breach of Promise to Marry" laws.

Engagement rings lost favor as the economy suffered during the 1930s, but that all changed in 1947. Copywriter Frances Gerety coined the phrase "A Diamond is Forever" for what would become the De Beers diamond company's widely popular advertising campaign, encouraging post-Depression era men to enhance their betrothals with pricey, sentimental rings and surprise proposals.

Just like that, a star of a sustaining trend was born.


RELATED: 18 Comforting Signs He's The One

2. On a less romantic note, the engagement ring that had to be "passed"

Simon Hooper, 28, from the UK, wanted to propose to his girlfriend. Unfortunately, Hooper chose to steal a ring rather than buy one.

While the jeweler was distracted, Hooper quickly swallowed the ring, which police later found by passing a metal detector over his stomach. Not to be deterred from his mission, when confronted with the evidence of the ring inside of his very being as shown in an X-ray image, Hooper insisted what they were seeing was merely a piece of foil he'd accidentally ingested.

Hooper was jailed for 12 weeks. As for the ring, police staged a three-day vigil outside of Hooper's jail cell awaiting its ... emergence from his chosen means of storage.


3. The one that almost got away

Nothing says romance like a proposal on the world-famous bridge, right?

As he knelt on one knee and opened the ring box while proposing to his girlfriend on the Brooklyn Bridge, Don Walling could only watch in horror as the ring slipped from his fingers and into the traffic below. In a moment of admirable determination, Walling sprang into the road in search of the ring ... and found it!

Of course, the victory meant having to dodge motorists, pedestrians, and a suicide prevention squad who thought Walling was trying to kill himself as he climbed down onto the main road.

The band was tarnished and bent, but the diamonds, and the couple's relationship, remained intact.


RELATED: 5 Subtle Signs Your Boyfriend Is Planning To Propose To You

4. The mysterious Chopard Blue Diamond ring

Natural blue diamonds are extremely rare, and the Chopard Blue Diamond ring features an oval-shaped 9-carat center stone set in an 18-carat white gold band encrusted with smaller diamonds.

While images of this bad boy are hard to come by, as is any record of current ownership of this particular gem, the late Princess Diana was gifted something similar upon her engagement to Prince Charles: the 12-carat blue oval sapphire surrounded by fourteen diamonds that adorn the finger of the Duchess of Cambridge (and future Queen of England), Kate Middleton.

5. Wal-Mart to the rescue

Since we're such suckers for heartwarming news, we're going to throw in another lost-and-found story for you.


After Arkansas newlywed Haley Reep Wagnon reported that she'd lost her 1.26-carat diamond engagement ring in a Wal-Mart parking lot, police scoured surveillance videos and spotted a 6-year-old girl picking it up from the ground.

“I saw a little girl pick up the ring in the parking lot, but I don't think the girl was trying to steal the ring and I don't think the family with her was even aware,” Detective Todd Crowson told reporters at the time. “She probably didn't even know that it is a real ring.”

They were able to identify the girl and her family from footage of the family vehicle, and just a few days later, the family happily returned the lost ring to a delighted and much-relieved Wagnon.

RELATED: How I Planned My Best Friend's Flash Mob Marriage Proposal


Denise Ngo is a freelance web writer and editor specializing in love, dating, and relationships. She is the Managing Editor of Loverish and a writer for PopSci.