Timeline:
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Red VS Ruby
At the beginning of her story, Red is a naive, sweet girl. As her Enchanted Forest Story is explored, we see Red mature from a naive girl to an overall much more steadfast, strong woman who never loses her core qualities of being warm, compassionate, selfless and loyal, be it towards friends or friends-to-be.

When we meet Ruby in Storybrooke, she is more akin to a rebellious teenager than the persona we have seen before, while under the influence of the unhappy end curse. She wears provocative clothing and heavy make up. Although we don't see much of it onscreen, other characters provide commentary or glimpses of Ruby being sexually very active, flirtatious and not in the least ashamed or even overly subtle about it, much to her grandmother's eternal suffering, eschewing hard work in the process when she assumes it's a punishment rather than a sign of trust in her capabilities. Ruby is easily discarded as a shallow good-for-nothing party-girl at first glance. However, some of her core attributes remain despite the much more forward, snarky and outspoken personality.

Both personalities have merged together when the curse was broken, leaving her with the strengths and weaknesses of both - fully aware of who and what she is, often ashamed for it but strong enough not to show this, friendly, flirtatious, always willing to help, selfless and self-hating, sweet and snarky. She accepts who and what she is - but that does not mean she likes it most of the time.

Human VS Monster
Already settled with near crippling self-loathing, as a consequence of the time bubble curse Ruby has lost her balance with and therefore control of her werewolf form. At her current canon point she believes that she once again hurt someone while transformed, and considers herself a monster deserving of punishment and even death. A lot of her usual characteristics are currently overshadowed by this, and it will take learning to control the wolf again for her to find her balance and true sense of self once more.

Empathy VS Temper
At her core, Ruby is a person who feels for other people, and will reach out to them based on that. She's seen preparing people's favourite foods without being prompted if she feels they're in need of a pick-me-up, and reaching out to friends and strangers who seem down on several occasions. Long before the show's events, as per the events of a canon novelization, she has even found it in herself to forgive the girl who tormented her in her youth.

On the flipside of that, as empathetic as she can be to others in need of compassion, someone rubbing her the wrong way will easily become the target of her temper. Her patience for friends is near endless, her patience for people she's not close to can be non-existent at times, and while she might not bite immediately, she will certainly begin barking fast. If you meet her with anger and snippiness, she'll quickly respond in kind, defensively lashing out, rise to bait and get annoyed fast. This trait is directly tied to her wolf - OUAT canon describes werewolves as "emotional" creatures, meaning they feel deep and strong, whether it be positive or negative.

Found Family & Pack Mentality VS Distrust of Outsiders & Grudges
As a werewolf, Ruby likes to keep her core people close, checking in with and following along with those she cares about, practically adopting them and the people they care about into a familial unit. This is in part inspired by the losses she's suffered, having once had a large family that was reduced to just her and her grandmother before her 13th birthday. And on the other hand, ever since temporarily finding a place in her thought-to-be-dead mother's pack, Ruby has learned the value of such close-knit dynamics. The happiness and wellbeing of the core members of her found family unit are paramount to her.

On the flipside of this, Ruby is wary of people she's not close to, keeping them at emotional arm's length even while being perfectly friendly, or being outwardly hostile to them, depending on where her found family stands on the matter. And while she can show empathy and mercy to people who wrong her, the matter is quite different when her "pack" is wronged. Ruby has killed her own mother for trying to go after Snow White, Ruby's best friend, and is extremely weary of Regina for having hurt her friends on several occasions, even when working alongside her. She holds grudges against people who have wronged people she cares about much more fiercly than people who have wronged her.

Protective Loyalty VS Blind Spots
While it might take time to get past Ruby's well concealed barriers, once she's decided to be invested in a person, her loyalty to them is unquestioning and knows practically no limits. Early on in the show we see her just give away her beloved classic car to a pregnant girl as a means of escaping a bad situation, and similarly she would rather be alone and defenseless than endanger Snow White while fleeing from a mob hunting the wolf. And while Ruby hates hurting people as the wolf, she does use her wolf form several times to fight against the Evil Queen's soldiers who threaten the wellbeing of her friends, stopping at nothing to protect them. That loyalty often extends to the people her loved ones care about too - Snow White is her best friend, and Ruby's protective loyalty shifts to include Prince Charming the moment he's in the picture.

This loyalty, however, can become blinding to her. She can get caught up in being protective, blindly risking trouble or repercussions for herself without second thought, for example by blatantly lying to law enforcement to protect someone she believes in need of that protection. Ruby can be downright carelessly giving to the people she values, offering endless support, backup, and unquestioning loyalty perhaps even against her own better interest. This also means that she can easily let the opinion of a loved one dictate how she feels about other people.

Caretaker & Helping Hand VS Self-Care & Self-Sacrifice
Ruby will go to greath lengths to take care of her friends, listening to their troubles and offering emotional support as well as backing up their endeavors. She rallies behind her friends' causes, encourages them on their path, and reaches out when she sees someone in need of help getting back on their feet - when Storybrooke is freed from its curse, Ruby immediately backs David (aka Prince Charming) in his efforts to organize the townspeople, backing his attempts at leadership, assisting where she can, and openly showing and stating her support in his decisions. Shortly thereafter, she spots a woman she's never seen before in the diner, Belle, and listens to her troubles, before immediately taking it upon herself to give Belle a place to stay and assist her in finding a job within the span of a 10 minute conversation.

On the sharp flip side, Ruby is slow to accept help or even ask for it, pushed into doing so basically only when others are in trouble - when wolf time is coming up after the curse breaks, Ruby wants to be chained up so she cannot endanger others, and it's the only reason she confides in needing help. Similarly she's shown at several points in canon to struggle with self-doubt, and only confiding in others when she's either arrived at a solution on her own, or when someone else is affected and in need of help. Ruby has poor self-esteem and a fake it till you make it mentality about many things, and where she easily encourages others, she doesn't believe in herself, despite all she's achieved. And even when help is offered, in her current canon point she is much more prone to throwing herself at an angry mob, believing herself deserving of death and punishment for who and what she is, even though she has friends trying to protect her, people who believe in her. Ruby still struggles with feeling useless and considering herself a failure, just a waitress who amounts to nothing. Most of her friendships seem defined by the problems others have that Ruby can help with, leaving her to fend for herself unless her problems become so obvious she can't keep them to herself.

Being a Rebel VS Being Rebellious
Ruby has a strong sense of right or wrong, particularly when it comes to people she cares about and people she finds worth protecting, going to great lengths to help where she can, which extends to her fighting on behalf of those people and fighting against tyranny and opression.

Those same rebellious, strong beliefs can also lead to her needlessly bristling at authority - Ruby doesn't like being told what to do by people who haven't earned the privilege, and is likely to get herself into trouble as a result.

Easygoing & Flirtatious VS Sharp Tongue & Assuming Negative Intent
Ruby is a people person - talkative, thriving when she can uplift others, and clearly at her happiest when able to engage other people. While she's only ever had one romantic relationship at her current canon point, she's implied and shown to enjoy flirting with others, both in a friendly as well as a very explicit fashion, and always rallies the proverbial troops around her loved ones.

Despite this, Ruby can have a tendency to assume she will be judged, considers herself the peasant among princesses, the girl to hook up with but not take home, and assumes others will dismiss her before giving them a chance to prove her otherwise. When finally confiding in Snow White after struggling with feeling like she doesn't belong, she immediately attaches a 'you probably think this is silly' to her confession. Ruby's self-worth issues are deep-seated and no matter the balance she achieves between her two identities or between herself and the wolf, no matter if she helps liberate castles, save princesses or eventually sits on Snow White's royal council despite her simple origins, this is something she continually struggles with. Tied to that is a habit of finding sharp words for people when she starts feeling defensive.

Shapeshifting (Werewolf)
During wolftime (3 nights: the full moon plus the night before and after) Ruby shifts into the shape of a large black/dark grey wolf at night. She cannot shift at will, but used to have an enchanted cloak that could suppress the shift/force a shift back into human shape. Currently, Ruby is not in control of the wolf, as a curse prevented her from shifting while stuck in a 28 year long time bubble. As such, the wolf will be a vicious beast that can and will hurt others, leaving Ruby with no memory of the night. It is possible for Ruby to regain balance with the wolf, which would mean she retains full control while shifted into the wolf. In wolf form, Ruby is impervious to most weapons with the exception of silver, as well as being a lot larger and stronger than a regular wolf would be (large enough for a fully grown woman to ride her, with her shoulders reaching nearly chest-height when the wolf isn't hunching down low.

Lycanthropy
Ruby is not a werewolf by curse or infection, but by heritage, as her mother was a werewolf too. It's not outright stated but strongly suggested that this bloodline is the strongest and highest ranking among the werewolvesin the Enchanted Forest, with Ruby's mother shown to be the leader/queen of her pack. However, the curse can also be transferred through a bite. At least in case of lycanthropy through bite, the curse fades with age (as seen in Ruby's grandmother). This does not seem to be the case if the curse is transferred genetically. Note: Ruby will not transfer lycanthropy to anyone voluntarily through her bite.

Heightened Senses
Even when not in wolf shape, Ruby has incredibly heightened senses of smell and hearing. It's difficult to sneak up on her as a result, as she could hear a normal person long before they make themselves known. Her scent of smell is refined enough that she can track a person by smell, or sniff out something unusual (like a heart in a wooden box buried in a forest. No really.). What she could tell about other people would be purely based on what other players communicate via narrative or in OOC communication, and only with the express permission of the player, of course, to avoid info-modding.

Canine Understanding
While not being able to speak with dogs and other canines, Ruby has a deep, intuitive understanding of them and what they're trying to communicate. On the flipside, dogs/wolves can tell she's kin.

Speed
Ruby has been Ruby has been shown to be able to run with supernatural speed. Canon does not go into detail, however given that she does not employ this power constantly and it's only ever truly seen when she rushes to physically catch someone about to commit suicide, it can be reasonably assumed that this power is limited, possibly allowing Ruby to have a burst of running incredibly fast for a short distance, therefore giving her more of a speed boost / headstart than making her naturally overall fast.

Weapons
Due to her upbringing in the Enchanted Forest, Ruby is competent enough with bows and crossbows to hunt game. In combat without weapons, she can hold her own enough to at least fend someone off and make a run for it, if she's not surprised/overpowered from the getgo.

Medieval Lifestyle
Due to her upbringing in the Enchanted Forest, Ruby is comfortable living in medieval-esque conditions in a forest including the day to day maintenance of a house, from building a fire to fetching water to providing for the household.

Cooking/Baking
Ruby has inherited her grandmother's cooking skills, who was running a bakery in the Enchanted Forest, and a diner/b&b in Storybrooke. Ruby doesn't consider herself as gifted as her grandmother is, but considering that she's learned from someone who's skills in cooking and baking are borderline legendary in their canon, it can be assumed that she's very good at what she does.

Business
Her grandmother started training her in keeping the books and handling other administrative tasks for the diner, intending for Ruby to one day inherit the business. She's got no degree, but has learned enough on the job to run a business like that.

Headcanons are canon compliant and framed to have no impact on cast mates in games. Mostly they inform how the character is played rather than becoming constant talking points. If ongoing canon reveals information that contradicts the information listed here, the headcanons will be updated/adjusted accordingly.

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