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Waypoint is an outgoing, enthusiastic, and adventurous Earth Pony living in Canterlot. Her main hobby is free running, which she also uses in her work as a delivery pony. Her cutie mark is a compass rose, and her special talent is sort of loosely defined as "knowing where things are".
Personality
Waypoint is quite an outgoing pony by nature, not afraid to push her way into a conversation and give her two bits, particularly if she thinks she can be helpful. Though she's often quite talkative, she's slow to make real friends, and values the few she's truly close to very highly. She doesn't keep herself very well-informed on the going's on around Equestria, so she tends not to be very opinionated. She's got very few hot-button topics, but if you happen to bring one up that you oppose her on, get ready for an earful. Her general philosophy is that ponies can do whatever they want as long as they're not stepping on anypony else's hooves, and that's how she lives.
Most of why she doesn't bother staying informed is that she just isn't interested in most news. If it doesn't impact her directly, she doesn't feel like she needs to know about it. She doesn't mind picking up a bit of gossip or hearsay when she jumps in on a conversation, but she doesn't often have much of it to share back, and doesn't put much stock in it. On the other hoof, if the news is something that she can have a direct impact on herself, she's all ears. She loves being involved with things and making change happen, she just doesn't see that as the case with most news stories.
Though she lives in Canterlot, she's not exactly a high-class pony, and neither is her family. She's sort of on the underside of the upper crust. She's not really an important pony herself, but she interfaces with them quite frequently through her work, so she knows how the system works and how to play her part. That is, the part of the silent help, doing what needs to be done but staying in the background while she does it. Every now and then she likes to pretend she's a rung or two higher up the social ladder though, particularly when it comes to attending parties.
Some might think her a tomboy what with her free running and her delivery service, but she's not lacking in femininity. On the contrary, she can be quite the girly girl sometimes. She usually wears at least a little bit of makeup, just around her eyes, and has several dresses for fancy occasions. She eschews them day-to-day so as not to inhibit her on her physical strenuous city explorations, the same reason she typically keeps her mane in a ponytail. She's been known to let her mane down or even put it up in fancier styles for suitably highfalutin affairs, though.
Cutie Mark and Special Talent
Waypoint obtained her cutie mark at a young age when she was on vacation with her family in Manehattan. During a visit to the Equestrian Trade Center, she became separated from her parents. They searched everywhere for her with the help of Trade Center staff before contacting local Guard Ponies. With the authorities on the case, the concerned couple returned to their hotel to wait for news, only to discover that Waypoint (newly cutie marked) had beaten them there.
Being from Canterlot, she wasn't intimidated by the big city and, though she was scared without her parents, she kept her head. After looking for her parents briefly, she decided that the best thing she could do would be to go home: they'd go there too eventually, right? The closest thing she had to home in Manehattan was her hotel room, so she set off for it without a second thought. Despite having never navigated the city before and being so young, she had a distinct feeling about which way she needed to go, and any time she was unsure, a quick pause and a look in each direction seemed to make up her mind without any meaningful cues.
This sense of where she is, where other things are, and which way she needs to go has persisted ever since. She never gets lost, has a knack for finding the fastest way to get somewhere (even places she's never been), and often finds things that others have lost, seemingly effortlessly. She can harness this power if she focuses on it, allowing her to get hunches about where missing things might be or find good restaurants in unfamiliar places.
Hobbies
Apart from searching for conversations to intrude upon, Waypoint likes to help ponies with things. She's got a few unique skills that she's happy to lend to anypony in need, and even if her particular talents aren't required, she'd much rather lend a hoof than sit idly by. She also quite enjoys spending time with her friends, usually just hanging out and chatting, playing games, going to movies or what-have-you. Most of her friends aren't as physically inclined as she is, so these times are probably the most sedate ones that she still enjoys.
When she's not hanging with her friends, she's usually out exploring the city, looking for new sights to see, new ponies to meet, and new challenges to overcome. You can usually catch her testing her limits by scaling buildings, vaulting gaps, and timing herself through common delivery routes. Very rarely will you find her both alone and idle unless she's resting after wearing herself out, a tall task in itself. Her innate sense of where things are comes in quite handy for her free running as well, giving her a good idea of just how far that jump is or whether there's a ledge around that corner without requiring her to double-check. She's learned to trust her instincts (which are rarely wrong) on these things, which enables her to make much quicker times than most ponies, even through areas she's not too familiar with.
Work
Waypoint's main job is as a delivery pony for several major Canterlot corporations. Nearly all of her deliveries are in-town, though she's been known to make out of town trips for things where speed isn't important. This is because while she can't come close to matching a pegasus for getting from town to town, she knows the streets of Canterlot like the back of her hoof, and she can come very close to matching them over short distances in the city with her free running prowess. With no scheduling fees like most pegasus delivery services charge and no full-time wage, she's a much cheaper option with virtually no downside for the corporations that know about and make use of her.
Apart from the deliveries, she's also sometimes sought out for her special skill at finding things. While she's not infallible, her knack for ferreting out lost items can be pretty astonishing sometimes. Most ponies don't understand how she does it, but that doesn't make the CEO who misplaced that vital document, or the sentimental pony who can't figure out what happened to that heirloom her grandmother left her all those years ago, any less grateful when she manages to recover them.
Miscellaneous
Waypoint never actually finished formal schooling. She's never been big on math or science or any other form of book-learning. She knows how the world works and is pretty good with ponies, but she's not a thinker. That's not to say she's unintelligent, she just doesn't bother with a lot of the details. She can read and write, a definite requirement in her delivery field, but she lacks both creativity and imagination, so neither are really pleasurable activities for her.
The one bit of writing that does do quite a bit of (apart from messages that she's supposed to deliver) is messages to herself. She's dreadfully forgetful and the only way she gets by is by writing reminders to herself and leaving them on her nightstand. Unfortunately, unless she has something to write her reminder down right when she learns about something, she often forgets to write herself the reminder later.
She has no siblings, just her father, Wayfarer (a now-retired earth pony sailor), and her mother, Tipping Point (a unicorn accounting consultant who works for several major corporations). She identifies strongly with her father's adventurous background and loves hearing his high-seas stories, but also loves having girl-time with her mother and really appreciates all the help she's given her. Most of Waypoint's delivery jobs with the big corporations are as a direct result of her mother's influence. When reviewing finances, she'll mention how much they could save if they hired on an independent delivery pony for in-town trips compared to a full pegasus delivery service or hiring a full-time delivery pony, and that she has somepony to recommend.
When she moved out of her parents' house, she wasn't well off enough to get an apartment on her own, and still isn't. Currently, she's splitting rent on a 3-bedroom apartment with a couple of ponies who grew up in her same neighborhood, Muscles and Shadow Bell. Muscles is a physically imposing body builder earth pony who's not the sharpest crayon in the box, while Shadow Bell is a diminuitive black pegasus who's very soft spoken and shy to the point of being reclusive. She doesn't get along particularly well with either of them, but at least tries to avoid outright animosity.
Though Waypoing doesn't live with her parents any more, she still quite enjoys visiting them frequently, and it's rare for her to go a week without staying a night at their house. With the nature of her business, she would see her mother almost daily regardless.