I remembered someone saying genderbend Gord stole Pinky's design and honestly, they were basically two sides of the same coin divided by gender roles, sexism, patriarchy, and other backwards practices. Bully was set in early 2000s small, American town with the technology and infrastructure still behind by a decade or two. It was safe to assume they would be leaning more on conservative values, evident in many dialogues from various characters where genders were brought up in taunting manner such as "come back here and fight like a real man" (Gord) or "you hit like a girl" (Gary) and straightforward insult "you filthy democrat" (Derby). Of course, there was countless other evidence which reflected the time and place Bully was set but those lines were just a few among many. However, the main focus as of current would be on the preps because the characters we're discussing were both from said clique.
First, their similarities. Gord and Pinky were born from affluent families, 'close' to Derby, and joined the prep clique. They were also both brunettes with short hairs who were spoiled rotten by their fathers. Last but not least, both Gord and Pinky were attracted to the less fortunate people AKA anyone below their (family's) tax bracket, hence why Jimmy was able to romance them. Interestingly, despite having what was essentially the same attraction, the game presented it in a very different manner.
For Pinky, she got the help of a new, mysterious bad boy with outrageous rumors surrounding him, because she's a Princess and she liked him. Unexpectedly, Pinky found a great dating partner in someone she shouldn't be involved with—Jimmy was blunt, got into fights a lot, and was not afraid to stand up for himself. But most of all, he came from an 'impoverished' and broken home. However, Jimmy also showed up on time, brought her bouquet of flowers, held her hands, and took the time to win a teddy bear for her. This contrast, especially for a teenage girl who was practically sheltered and spoiled, provided its own excitement. My absolute favorite part of the Carnival Date was that it was one of (if not) the only time where the two basked in the joy of normalcy, two teenagers spending time together, not worrying about the future—a brief escape from their chaotic daily life. Overall, the game presented this in a positive and romantic light. There were no consequences that followed, indicating Derby hardly cared about what Pinky was doing with another boy. I could go on and on about why Pinky's quests made her the best and most bittersweet girl in the game but it'll be explained later.
For Gord, he was having fun with an attractive girl who was notorious for cheating behind her boyfriend's back with countless boys. All while knowing about Johnny's hot temper and severe jealousy, which she explicitly enjoyed watching him or other boys fight for her. It was obvious the game presented her in a negative light and we're also supposed to see Gord's affair with her to be negative because Jimmy was on Johnny's side at the time. There weren't many details on what their dates entailed except a few suggestive dialogues alongside automated flowers and kisses in a quest where we took pictures of them. What we knew for sure, Johnny cared about Lola, so much that he taught Gord and his friends a lesson, which led to the events of The Rumble where the preps and the greasers fought each other. The consequences were quite severe and clear. Gord and Pinky, while both were attracted to the poor enough to date them, had strikingly different presentations and outcomes. Pinky's affair was presented in an overall encouraging and bittersweet sense, the outcome was inconsequential to the plot. Gord's affair was presented in a discouraging and scandalous manner, the event leading to nearly the entirety of Chapter 3. Pinky was a spoiled but sweet girl who got stood up by her date. Gord was a rakish idiot who laid his hands on someone's girl.
Why was it so different when in essence it was the same thing? Well, it would be too easy to say because they're all different characters with different dynamics. The other answer was because the game centered around Jimmy, despite all the crap he had gotten throughout the game, he still prevailed—it was a power fantasy of sort. Imagined if you dated the girlfriend of the richest boy in school who happened to be interested with poor people. Gord and Pinky said poor people were more real, which I believed was due to their inherently classist and pretentious upbringings to act as if they were above everyone because they had exorbitant amounts of money and power over other people. This led to them developing a certain way of thinking and speaking which affected on how they interacted with others—hence it was their way of admitting that rich people were fake, superficial. They had their lives practically set by their parents, Pinky was going to marry Derby in the future while Gord was studying to be a lawyer. To them, the ordinary people, did not follow the same standards and strict future their parents set in store, hence they had broader place to grow and be their own individuals—something which I assumed they weren't able to have, was it worth owning a mountain of wealth if you were to live like a finch trapped in gilded cage?
Now, the important question, how much did gender roles affect them? From a general standpoint, Pinky was exempted from fighting in the story because she was a girl. At best, she watched others fight and cheered on them. In comparison, Gord actively joined fights and pranks. Moving onto a more exclusive distinction, which was unique to the preps—keeping the blood pure. Both Gord and Pinky accepted this practice in a casual manner, treating it as if it was normal in the first place. However, while Gord thrived, Pinky openly disliked being bound to Derby. Gord said, in his unused voice line, that his father had more mistresses, implying affairs was the norm, even something to brag about. This might be why Gord was described as a rake because he respected and possibly looked up to his father, if his father did it then it must be fine. Pinky, on the other hand, felt as if she was responsible for her parents divorce. I found it rather disturbing how young her stepmother was and why she dressed up like her. My theory was that Pinky's father lost his wife during childbirth and his daughter grew up to be her spitting image. He projected the feelings he had onto Pinky and later, his new wife. Pinky thought that her step mother dressed like her, when in fact, she dressed like her late mother.
Both Gord and Pinky were spoiled by their fathers but had different expectations. Gord's father wanted him to continue on his footsteps while Pinky's father wanted her to be married off to a rich husband. Gord was encouraged to get a job, be a lawyer. Pinky was specifically told not to worry about work, she simply had to marry a person of significant wealth. This gave her little to no financial autonomy in the future, unlike Gord where it didn't matter if he would be divorced, he made money and if he lost a few, he would be able to recover with given time. It didn't matter if he lost a trophy wife, he had mistresses and was more than able to make one of them his new wife. Pinky didn't have such an option. She's dependent on her husband, if they divorced, Pinky would be left with just her family's inheritance. For simply being born a girl, her options were far limited than a boy's. It can be said about girls in general but at least they had the freedom to pursue a career or a person they truly loved, which Pinky lacked.
Pinky spent her teenage years mingling with people beyond her reach, grasping at normalcy and authenticity she wouldn't be able to feel in her usual setting, Jimmy was akin to a dream come true, raw and honest, it was unlike any she ever experienced before. I assumed Gord had similar sentiments with Lola, while she may not be in love with him, she enjoyed his attention. The main difference between Gord and Pinky was that, Gord would be able to pursue Jimmy into adulthood, Pinky wouldn't. Why? Because one was raised to be the heir of the family while the other was raised to be a political tool, a drastic difference simply over their assigned genders. Pinky would treasure her time with Jimmy, keeping the cheap teddy bear until the color faded, away in a special box, deep within her closet. Meanwhile, all Gord had to do was chase after Jimmy with determination. They needed a lot of talking for sure but the point was that he had a chance without risking his status, she didn't. If their genders were switched, Gord would be more similar to Pinky and Pinky would be more similar to Gord.