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Michael

Cutie marks are kind of representational or nebulous, they aren't always literal. So Pinkie's is balloons, but her special talent is making other ponies smile and throwing celebrations/being a party planner. Applejack's special talent is working with apples and on the apple farm. It is explained more a bit later on, but that's the gist of it. (it's also explained a bit in the episode but I figured I'd clarify)

Awkward Segway

The episodes aren't always in chronological order. Seasons 1 through 3 all take place over the course of a single year, so even some season 2 episodes take place before some season 1 episodes.

Jeff Spencer

and here we meet the best ponies and the worse. the CMC are the best just 3 kids looking to see where they belong and Diamond Tiara and Silver Spoon the trash of MLP they do get better WAY further in the show but yeah other then angel bunny these 2 are so hated this point in the series. as for scoots she is dashies #1 fan they don't share much at this point in the show but it evolves later in the show. also the names yeah... some parents hated their kids no lie but they do grow into them. oh and fun game for you if you wanna try it. not sure if ya drink booze if not choose your favorite drink and drink everytime they point the camera at their asses. if its alcohol you will be shit faced quick.

Pinkie_applepie

These are two of my favorites! So glad you enjoyed them as well!

Thine Tiny Equine

Continuing off another user's comments, Seasons 1 and 2 are pretty out of order. It's not worth trying to piece it all together, too much to juggle. There are a few season 2 episodes that we know take place right where you are though (after 14/15), though that's about all I know about. Post season 2 all of the episodes are in order though. For the sake of sanity, remember that MLP starts during the first days of summer and season 3 starts in summer, putting all of seasons 1 and 2 in the course of an exact year. Which works really well! 52 episodes, every episode takes place in its own week.

Sammy

silver spoon's cutie mark is a reference to the saying "born with a silver spoon in their mouth" meaning born very rich and spoiled. i don't remember if diamond tiara has a reference aside from "spoiled princess" theme lol