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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.

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):

Red: Rarity

Blue: Cheese Sandwich

White: Nightmare Moon

Green: Babs Seed

Orange: Twilicane (wat)

Grey: Spike

Any other color: Granny Smith

No shirt: Silver Spoon