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Twilight Sparkle - Known a few, crushed on them pretty hard. Too chickenshit to do anything. Anyway, a fun lot if you can get them to trust you but they do need their space. That said, gain the trust and attention of bookish girls isn't easy.
Fluttershy - In case my above statement about being chickenshit didn't clue you in, I'm a Fluttershy, only one I know actually, for the very good reason that two socially aversive people are very unlikely to reach out to each other. Also, I'm a guy just to be sure.
Rainbow Dash - Rainbow Dash, as the ambitious tomboy, is a character type I saw less and less of as I got older. Always saddened me a little, I kind of envied the confidence and openness without the insistence of opening people of of the Pinkie Pie.
Applejack - Actually, most of the Applejacks I've met have been guys, though there have been ladies as well. Never really form a lasting friendship with any of them, though I will say they were a joy to work with.
Rarity - IRL, Raritys kinda annoy me. Not that the ones I've met were bad people or even overly obsessed with fashion/appearance, just wildly divergent interests.
Pinkie Pie - They also really annoy me, though often do my best to hide it. The ones I've met often try really hard to be cheery and to spread that cheer around. Which is all well and good except they tend to get a little too close and, well see the Fluttershy entry.
Eh, just a brief bit piece about people I've met that showed some of the character traits. Here have a random macro