I have a thing for couples who look like opposites; dark and light colors, square and round shapes, and as in this case, short and tall.
 
I headcanon Pipsqueak as having some kind of dwarfism or similar, due to just how tiny he is compared to the other foals at the school. And I also headcanon that Apple Bloom will grow up into a beanstalk, so the result from those headcanons was pretty much inevitable. I just think they look really cute together I also like that they both have reallt different accents, and I think their peronalities work well together.
 
I’ve said it before; I can ship just about anything if I really think about it for more than 2 seconds.
 
I also gave adult Pipsqueak a beard, because I liked the way it looked. I wasn’t sure about his cutie mark, but since there isn’t  
any canon info (yet) I decided that in this version his special talent is seafaring, and his cutie mark is a golden sextant. This is completely based on how his nightmare night costume was a pirate, and how he liked Luna (thus the stars I guess?)