Valentine Adelaide (full name Valentine Vivien Adelaide) is a 26 year old Hitman for the Lammergeier Syndicate. He's a man who crossdresses, and identifies as male despite appearances. His attire of choice most often is a Victorian-era styled maid dress. As with the rest of the syndicate, he wears black leather gloves. His weapon of choice is a katana (named Julia) due to his lack of depth perception and a preference for blades. His syndicate alias is "Black Widow".

Personality wise, Valentine can be best described as unhinged and flirty, yet carefree. He says he doesn't care what people think of him, so he'll openly lay anything he's thinking of on the table and not stress over judgement. Speaking his mind with little filter is just how he operates. He often uses flirting as a weird way to communicate and doesn't always mean what he actually says. He's just trying to be friendly. People who are around him long enough know to just brush him off. Despite those oddities, he's a social butterfly and gets along with most everyone he talks to, so long as they don't judge him for who he is. He likes people (mostly), he likes having fun with them. But if they push his buttons, he's easily "bratty" and short-tempered with a low tolerance level. Even though he seems to be a little airheaded sometimes, he's sharp as a tack and is an expert at analyzing people-- one of his assets as a hitman. He'll pick up on things that not even the smartest around him (Boss, usually) notice and use it as an advantage.

Though true that he's a full-time crossdresser as a personal fashion choice and for comfort, he also uses it to feed his own perversions. Valentine especially likes the attention he gets from it... But only of the positive variety. He hates the feeling of wearing mens' clothing and pants, only wearing them when absolutely necessary for a hit. Besides them being tight and constricting to him, he remarks that it "doesn't feel like Valentine". He's been this way since he was a child, even if he couldn't actively dress how he wanted full-time until later. He's still very traditionally masculine in other aspects despite appearances (like a deep voice and frat-boy behavioral tendencies).

He has a serious penchant for one of his bosses in particular, Aurelio. He calls him Boss, along with other nicknames. Valentine is often seen around him, clinging to his arm with a wide smile across his face. They both have a long history together, with Valentine initially being hired as his apprentice. He wishes a lot of romantic and sexual things with him, but is pushed away due to their work relationship and other factors. The two are together enough to have him be considered as Aurelio's bodyguard, especially on occasions where he needs his protection. As much as he's rejected, he says Aurelio is the only man he'll ever truly love. But he's just happy to be with him regardless as his best friend and apprentice, as much as it frustrates him. Even just a brief description of their relationship scratches the surface of his "deep feelings" for Aurelio... Which is something he'd say and call romantic. They have an inseparable bond and are rarely seen individually. He's just a little obsessed with him... Just a little.

He doesn't have a right eye, the area covered with a patch. Incessant toying and prodding objects into the remaining socket is something he mindlessly does as a bad habit and does to scare others, though it's also a fetish of his. Due to assorted things being pushed too far in, the result has been brain damage to his frontal and temporal lobes. Though, he could care less about that part, even if it makes his mental health issues worse. If you ask him how he lost it, he avoids the question with a blunt answer. (It's a very sore subject.) He's more prone to migraines for various reasons, and when they happen they tend to be disabling.

Valentine has psychosis and shows signs of other unknown mental illnesses, often not understanding his own mortality, and at times reality itself. He'll have bouts of aggression where he's bitey and irritable, but they're erratic and not long-lived. He has a short temper with a few things that will instantly make him fly off the handle. And other times, he'll detach himself from the ability to feel emotions, seemingly catatonic and not receptive to even the things he loves. He occasionally has delusions, more often semi-realistic than not. He isn't a person that regularly feels afraid of anything, but in those moments even Boss can scare him from paranoia. In the midst of an episode he won't be "aware" of the unusual things he's saying or doing, and will have a foggy memory of it once it ends. He refuses to see a doctor or get medicated for it, having bad experiences with medication in the past. He remains undiagnosed for anything else. He can't feel much in terms of empathy besides when its directed at Aurelio. Because of this, at times he doesn't understand what he's doing wrong, the consequences of his actions, or how others truly feel. The emotional disconnect between himself and others continues to enable his behavioral issues without the ability to learn in sight.

Valentine's perception of pain and pleasure are mixed. Unable to tell the difference, he willingly throws himself into compromised positions to seek the thrill he's craving. With his job as a hitman, Valentine isn't afraid of things like death, but is drawn to it to a detriment at times. He enjoys the blood and gore of it, and even likes being on the receiving end. Though of course what he can do with those fantasies can't often safely be enacted. Aurelio does his best to curb his lack of impulse control and general defiance, but he can only do so much, especially when he thrives off of negative attention for an excuse to retaliate. He's Valentine's biggest support when it comes to his mental health issues and refuses to abandon him even if he frequently acts out. Deep down the reason why he acts the way he does isn't purely from mental illness, it's just the kind of person he is... Along with other troubling issues from his past shaping who he is in the present. Basically, he went from being a problem child to a problem adult.

Due to his mental issues, hobbies, and job, he lives his unpredictable life to the fullest, never knowing when it may end. And despite all of his shortcomings he enjoys the time he spends alive, especially when it's with a man he finds cute, like Boss.