The Saddest Love Stories Of All Time

Tales of romance proving how strong real love can be

With Valentine’s Day just around the corner, we are reminded of the greatest love stories of all time. Cleopatra and Mark Anthony, Romeo and Juliet, Pocahontas and John Smith – they all had one thing in common – yes: passion, love, lust but most notably tragic endings.

Maybe that’s why they continue to remain as the most memorable ones.

Here are a few more saddest love stories from history and legends to tug at that hopeless romantic heartstring of yours.

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2. Orpheus & Eurydice

saddest love story ever

Painting by Ari Scheffer (1795-1858), public domain image.

In Greek mythology, Orpheus, being the son of a muse, was able to play the lyre beautifully to the point that nothing could resist his beautiful melodies. Soon after he fell in love with a woman of unique beauty and grace, Eurydice, whom he married and lived happily with but only for a short amount of time. One day while Eurydice was wandering in the forests with the Nymphs, a shepherd – Aristaeus became beguiled by her beauty and started chasing her. Startled, she fled and tumbled into a nest of snakes, receiving a fatal bite to her leg.

After Eurydice’s death, Orpheus one day decided to descend to the underworld to see his wife. He managed to use his talents to charm his way through the underworld and present himself in front of Hades and his wife, Persephone, unharmed. Orpheus played his lyre again, this time melting Hades’s heart.

Hades told Orpheus that he could take Eurydice back with him but under one condition; Eurydice would follow him while walking out to the light from the caves of the underworld, but he should not look at her before coming out to the light or else he would lose her forever.

Thinking it was a simple task for a patient man like him, Orpheus was delighted. Orpheus thanked the gods and left to ascend back into the world. At just few steps before reaching the light, Orpheus became anxious as he could not hear Eurydice’s footsteps. He feared that the gods had tricked him so he turned back to look behind.

Eurydice was indeed behind but because of Orpheus’ stare, she vanished for the second time. Drenched in sorrow and guilt, Orpheus vowed to never love again.

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