Here are Equestria's known long-lost lovers: Cranky Doodle Donkey and Matilda Donkey. Cranky might be crotchey old grouch of a jack who's reluctant to loosen up, but he has a kind heart. And to even out his temper, his donkey damsel wife, Matilda, will always lift her sweetheart's spirit.

A long time ago, Cranky was a handsome young jack who found true love when he first met the beautiful jenny, Matilda, at the Grand Galloping Gala. It was a very magical night for them. After the Gala, Cranky came to Matilda's room, but didn't find her, though Matilda left him a note which he never saw. He spent the rest his years going from town to town searching for her, until he finally conceded and came to Ponyville to retire from his search, growing despondent, cantankerous, and "cranky." Matilda, however, left Cranky a note telling that she was moving to Ponyville, and she waited for him there the whole time. However, they would soon be reunited… but not in a way either donkeys expected.

When Cranky arrived in Ponyville, he was greeted by Pinkie Pie. The hyperfriendly pony loved nothing more than making ponies smile, but Cranky would not even smirk. In fact, the grumpy jack was more annoyed by Pinkie's attempts with being his friend. After Cranky revealed his lifelong journey searching for his "special friend" (and after accidentally ruining his scrapbook that contained the only physical reminders he had of said friend, Pinkie Pie remembered that Matilda has some of those same items in her scrapbook, and so she brought her to back to her "Doodle." Overjoyed to be reunited with his long-lost love, Cranky smiled for the first time in years, and thanked Pinkie for reuniting him with Matilda and accepted her friendship. The two donkeys were back together again. Then a year later, they would seal the deal with a wedding!

Of course, on the day they would be married there was a bit of a hiccup. It was supposed to be the day after, but thanks to Derpy there was a ridiculous misprint on the invitations. To make things more complicated, a bugbear was on a rampage in Ponyville, and the Mane Six, including Pinkie Pie — who was to serve as the due-to-be-wed's wedding planner — were fending it off! With the six mares occupied, the other citizens were left to prepare the wedding themselves. In the confusion, Matilda got her mane done at the spa, where she met Cranky's groomsman, Steven Magnet the sea serpent. Meanwhile, Cranky, after complaining to Derpy for the wedding get misdated, lost his toupee before the ceremony. Fortunately, Steven gave him a replacement made from his own beloved moustache. The wedding soon took off (however, the Mane Six were accidentally locked out by Derpy after defeating the bugbear). Mayor Mare presided over the wedding. And so the two donkeys became husband and wife. And this time, they will never be apart again.


This was the first time I made vectors of both Cranky and Matilda. I had to improvise here and there, but I believed this interaction works perfectly. The sentiment really fits them. :nod:

Sorry for changing the subject, but I wish we got to see more of Cranky and Matilda when they were young adults (that, or at least more donkeys). I'll see if I can make vectors of them.

There are more Hearts and Hooves Day pics like this to come, so be ready. Heart Love Happy Valentines Day Being silly together is so much fun … Heart Icon (Happy Valentine's Day!)