I saw a lot of versions of these. Decided to do one myself. Deal with it.
January: You have a crush on X. Then Y breaks up with you.
February: You helped Y cooking breakfast for X.
March: X gives you a hug, and Y is jelaous.
April: You, X and Y go treasure hunting.
May: You and Y sing a song for X.
June: You, X and Y go to the beach.
July: You and X pull a prank on Y.
August: Y is now your teacher.X is now your classmate.
September: You and X go back in time and meet the young Y.
October: Go trick-or-treating with Y to X's house.
November: Play videogames with X and Y.
December: Go skydiving with Y and fall on X.
1: Fluttershy 2: Sweetie Belle 3: Applejack 4: Derpy 5: Doctor Whooves 6: Twilight Sparkle 7: Flash Sentry 8: Diamond Tiara 9: Apple Bloom 10: Bon Bon 11: Rainbow Dash 12: Button Mash 13: Discord 14: Cheerilee 15: Scootaloo 16: Big Macintosh 17: Lyra Heartstrings 18: Amethyst Star 19: Mr. Carrot Cake 20: Vinyl Scratch 21: King Sombra 22: Rapidash 23: Pinkie Pie 24:The Headless Horse 25: Splitfire 26: Major Mare 27: Queen Crysalis 28: Princess Luna 29: Fluffle Puff 30: Prince Blueblood 31: Octavia
Y (color of your shirt):
Blue: Cheese Sandwich
White: Nightmare Moon
Green: Babs Seed
Orange: Twilicane (wat)
Any other color: Granny Smith
No shirt: Silver Spoon