This story is a sequel to Know your Mare

Pipsqueak, how the years have gone by. They've watched you grow from an eager young rapscallion into a handsome, strong stallion. All the while they've been moved, touched, and all around attentive... And what they've noticed is that you don't have a girlfriend! And as your guardians, that's something that won't be stood for. Even if they must ravage all of Ponyville, they WILL find a girl just right for their little Pippy.

Editor: TheNoodleGod2012 and Meester

Art done by: Egophiliac

Let's just say your luck with the mares isn't all that great, two months in Ponyville and you've had your heart stomped on more times than you can count. That coupled with the fact you've lost your job, your house, and have barely enough bits to feed yourself means your life isn't exactly going so great. And after another botched attempt at a relationship you're ready to swear off of the whole dating game for good.
But after a night of drunken debauchery you awaken to find yourself in the service of Ponyville's premiere fashionista, you're willing to forget your previous pledge to the single life after she proves herself to be the kindest and most generous pony you've ever met, but only time will tell if she'll be your future lover or the next in line of a long list of mare's who you'd rather forget.