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I've seen lots of these games recently and thought I would make my own spin on it.

January: You and Y have a snowball fight with X as the judge.

February: X and Y throw a surprise party for you.

March: Y makes you cry and X cheers you up.

April: You and Y play a sport together with X as the ref.

May: You can choose what you want to do.

June: You and X go to the beach.where Y gets pinched by a crab, drenched, and other assorted misfortune befalls them.

July: You and Y go swimming in X's pool while X acts as lifeguard. You almost drown, X saves you, and you reward them with a hug. Aww...

August: You and X are in a play while Y watches.

September: You and Y are sick while X acts as your nurse.

October: You scare Y with X each in whatever costumes you choose.

November: You and Y eat a Thanksgiving dinner that X made especially for you.

December: X acts as Santa and delivers presents to you and Y.

Y's:

Monday: King Sombra

Tuesday: Trixie

Wednesday: Sunset Shimmer

Thursday: Gilda

Friday: Discord

Saturday: Diamond Tiara

Sunday: Flim & Flam

X's:

1: Princess Celestia 2: Luna 3: Rarity 4: Scootaloo 5: Sunset Shimmer 6: Apple Bloom 7: Sweetie Belle 8: Your choice

9: Daring Do 10: Pinkie Pie 11: Derpy 12: Dinky Doo 13: Soarin 14: Cheerilee 15. Big Mcintosh 16. Shining Armor

17. Twilight Sparkle 18. Berry Punch 19. Nurse Redheart 20. Spitfire 21. Fleetfoot 22. Babs Seed 23. Lyra 24. Bon Bon 25. Spike

26. Your Choice 27. Coco Pommel 28. Cadence 29. Braeburn 30. Trenderhoof 31. Fluttershy

So in my case, since I get to choose, Rainbow Dash saves me from drowning while working as a lifeguard while I swim with Trixie. I like this a lot!