This is a collection of short stories about the first dates of some of Equestria's couples.

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Button Mash wants to ask the filly named Sweetie Belle whom he has a crush on to be his Special Somepony on Hearts and Hooves Day, but he never seems to have the courage to. Will he ever be able to ask her?

On Christmas Eve The Cutie Mark Crusaders try to stay up to get a picture of Santa Hooves.

Short Story: Cheese Sandwich wants to tell the mare he has liked since he was a colt that he likes her. But how should he? So he asks Rainbow Dash for advice.

Rainbow Dash is excited to be spending her first Hearts and Hooves Day with Soarin, but when he doesn't come or say anything Rainbow gets worried that he has forgotten. So she starts looking for him.

Short story: Big Mac wants to do somthing special for Cheerilee for Hearts and Hooves Day but doesn't know what to do. So he asks Applejack about what to do.

Rainbow Dash find's a note on her door saying to meet somepony at midnight on Christmas Eve and doesn't know if she should go, so she asks some of her friends what should she do.

Cover art by: Nineveh