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Chris and gender
Similar to the topic of faith and the topic of morality, Chris's actual beliefs on gender and how it is classified are more complex than his stated beliefs. For someone so preoccupied with gender identity, Chris displays a staggering ignorance of how either gender typically behaves, and his views of both genders are extremely warped due to him taking the stereotypes he is presented with in television and music at face value.
Chris repeatedly asserts his reverence of women, and seems to have a comparatively glowing opinion of them, stating that he finds women "empathetic". But, as stated at the beginning of the article, the truth is more complicated. While Chris has always preferred female friends, and is known to be far more accommodating of lesbians than gay men, even going so far as to identify as one himself, in truth, Chris has a distinctly sexist view of women. Based on his failed attempts at getting girls at the mall, Chris views females as hyper-sexual, preoccupied with shopping, given to conversing with others for hours, and fixated on getting married and having children. This is highly evident in his female characters in Sonichu. As a matter of fact, In Sonichu #9, he referred to women as another species. This seems to be hyperbole, but considering Chris' abysmal knowledge of the sciences, it is difficult to be sure. His Rosechu character who is a living embodiment of how Chris believes all women behave, has a "personality" which consists solely of the traits listed above, which is considered ironic as Chris constantly tries to show Rosechu with a passion for Women's Rights. Despite trying to portray them as being equal in power to their male counterparts, Chris rarely depicts Rosechus fighting, more often simply leaving them on the sidelines of a battle to wail like damsels in distress, even when their boyfriends are in mortal danger. Even outside battle, they tend to be little more than organic sex toys for the Sonichus.
Chris has harbored a deep hatred for men ever since his teenage years, because he was bullied in grade school (largely because of his bloated ego making him extremely annoying to be around), not to mention the fact that Chris is known to fly into fits of jealous rage whenever he sees a man more successful than him, especially if that man is getting some and he isn't. This gradually blossomed into a general distaste for masculine traits such as body hair; indeed, in his nudes it is apparent that he is surprisingly meticulous in shaving his body hair, certainly compared to other aspects of grooming. He also has stated, as shown in this video, a disgust for "topless men" and encourages men to wear muscle bras so he doesn't have to see their nipples. He even made a (now somewhat outdated) short list of the men he doesn't consider "jerks", which included himself, his father and Santa Clause [sic].
Since becoming a "tomgirl", Chris's misandry has not abated. In recent years he has variously referred to men in general as "barbarians" and "Neanderthals", which, coming from him, are rather ironic accusations for a number of reasons.
Transvestism and transgenderism
It has been speculated for a long time that Chris has had gender issues. In 2005, he created Crystal Weston Chandler, which is widely believed to be a result of his autogynephilia, the fetish of seeing oneself as female. In Christian Weston Chandler's FUTURE MESSAGE, he mentioned that you should try out the opposite gender's toys while keeping your original gender in mind, possibly indicating that he may have been in denial about transgenderism long before becoming a tomgirl. He also wondered what he would be like if he were born a female.
In April 2011, photos were leaked by Surfshack Tito showing Chris dressed in women's clothes. Soon after Chris announced he was a "Tomgirl". Chris being a tomgirl has resulted in him wearing feminine clothes, a brief attempt at piercing his taint, and growing long hair. Despite this, Chris still rigidly maintains he is attracted solely to women.
There is still speculation as to why he has done this. Chris may have believed that joining the female community would aid his Love Quest, which naturally it hasn't, and indeed, any sensible person can see that identifying as a lesbian actually shrinks his pool of potential sweethearts, given that lesbians are a minority group.
However, Chris has recently made several telling statements that indicate he believes that he can use his gender confusion to his advantage. For example, on various occasions, Chris has made statements to the effect of him being "compatible with all women", or that he can "go any way [a woman] desire[s]". Statements like these show that he believes that by identifying as a female while remaining biologically male he can appeal to women of all sexualities, although it remains unclear if this is his main reason for crossdressing, or indeed whether it was a premeditated reason for it at all, or merely an idea he came up with later. This too is pure folly; a willingness to date folks with penises is hardly a given among lesbians, and most straight women would be put off by Chris's crossdressing. Not to mention that both lesbian and straight women alike would probably be put off by the sheer desperation he displays in essentially saying that he'd be willing to change genders just to get laid, and that's without even considering the squalor he lives in, his bizarre, unkempt appearance, or his many personality flaws.
Chris also may have done this in hopes that trolls would stop suggesting he likes "the wrong gender". Some just believe Chris has been TRUE and HONEST and has always felt this way, despite little evidence. Regardless of the reason, the Tomgirl Saga has continued to this day. Despite being self-described as a "lesbian in a male body", and even showing off pictures of him slapping Human Rights Campaign stickers all over his car, Chris still seems to be rendered very uncomfortable by gay men, although he has slowly backed down from his bigotry towards them, possibly recognizing that his disdain for them is irrational even by his standards.
However, being transgender does not stop him from prejudice against other transgenders; during his quest against Jeff/Francine, who is also trans, Chris calls her a "pretty little lady-man", a "he-she", and even "Mistress Jeff" showing that even years into his transformation into a Tomgirl, Chris is still Chris.
—Chris' beliefs on Non-Binary Genders
Given how complicated of a topic gender is to tackle, especially today, people will tend to argue about what classifies as a "gender" and therefore some people might argue that there exists more than two. In Chris' case, believing everything he sees without giving it a second thought, also concluded that there really are more than two genders simply looking at a Facebook post about how Facebook is allowing their users to identify themselves as 58 different genders on September 17, 2016, taking it to mean that there are in fact 58 genders.  The next month, Chris is interviewed on the same topic, and is asked how many genders there are, and simply says there are 58 all because of that same Facebook post. 
In the comic
Chris, already conflicting with his own gender identity, also decided to give his avatar in the Sonichu comics the same exact characteristic since Sonichu 11. Once again, despite looking completely different from his real-life counterpart, decides to draw his avatar with the traits he's always desired since becoming a tomgirl, such as bigger breasts and wider hips, revealing very much of what kind of results Chris wishes to get simply from watching Subliminal Frequency Hypnosis on Youtube instead of saving up his money to get a sex change.
Likewise, Chris decided to change his Sonichu form to a female Sonichu form. The only real difference between Chris' old form and his new form is that his newer form has added breasts; a functioning vagina, uterus, and ovum; eyelashes; the trademark female Pikachu tail; and the color of his shoes change from black and white to turquoise and lime green. At this point in time, Chris-Chan Sonichu's species is highly questionable, given how Chris never implied that his new form was, in fact, a Rosechu, and instead refers to it as simply a "female Sonichu form", and the character is still called Chris-Chan Sonichu. Even though Chris has suggested renaming the character "Chrissy-Chan Roeschu", it still begs the question as to why Chris hasn't decided to make his new form into a Rosechu in the first place, seeing how female Sonichus theoretically don't exist and that Rosechus are essentially the female counterpart of Sonichus. And despite giving the character the new and more logical name, he never implied that he'd do a redesign on the character itself to give it Rosechu traits.
- Mailbag 27 - Is Chris hitting on Bailey Jay?