Soon after, however, Skyler was quickly shown to be a bully within her high school, with Cara (having pulled bullying pranks with her friends in her hometown) joining her and Quinn in their actions. When the time came for their class to nominate someone who Homecoming Princess, Skyler concocted a scheme with Quinn (much to Cara's unease) to nominate classmate Grace Young against Skyler, believing she would easily win the vote due to Grace having Down's Syndrome. However, Grace ended up winning the vote and title of Homecoming Princess, much to Skyler's outrage and dismay.
Later on, Cara revealed to Skyler and Quinn in the school locker room that she had been asked to the dance by her crush Brandon Powers, who also helped Ben Powers (Brandon's brother, who also had Down's Syndrome) ask Grace to be his date and agreed to let them ride to Homecoming with them. Skyler, still bitter over losing the Homecoming title to Grace, angrily refused to let Grace and Ben join their ride, and also joined Quinn in throwing deragatory slurs about Grace, referring to her as a "mongoloid". Eventually, Skyler conceded and said she would let Grace and Ben join their group to Homecoming, due to Quinn reminding her that she would likely lose Brad as her date if she refused. Later on, Skyler and Quinn appeared to begin helping Grace's campaign for Homecoming, helping Brandon and Brad make banners and passing out flyers asking their classmates to vote for Grace.
But in actuality, Skyler was plotting with Quinn to pull their "Senior Prank" on Grace, while also intending to set up Cara to look like the perpetrator. While discussing their plan, the evil Skyler accused Cara of (in her mind) ruining her senior year, while throwing more insults towards Grace and Ben. On the night of Homecoming, Skyler's prank had Grace being crowned Homecoming Princess (a result of Quinn rigging the vote) and being asked to sing a song by Cara (who was reading from cards written out by Skyler). As Cara attempted in vain to stop Skyler, Grace began singing, leading her to be laughed at by her classmates and to suddenly begin having heart troubles. In response to Grace passing out on the stage, Skyler callously proclaimed that the prank was Cara's idea, with Cara's pleas of innocence to Brandon and Ben falling on deaf ears.
After Grace was hospitalized and Cara began facing harassment and isolation at school as a result of Skyler's actions, Cara went with her mother Nancy to confront Skyler and her mother. Later on, Skyler and Quinn joined Cara and her parents to visit Grace in the hospital, bringing flowers and balloons as gifts to her. After expressing shock at the severity of Grace's conditions, Skyler and Quinn revealed to Ms. Young that they was the true masterminds behind the prank and that Cara had no knowledge of their plan, sincerely apologizing for their actions. Ms. Young reacted to the girls' apologies by lambasting them for their cruelty, leading a remorseful Skyler to run away in tears. Skyler was later seen in attendance at Grace's funeral when she succumbed to her heart defect, though her ultimate fate is left unrevealed.
- "No! No way! I don't care how cute it was. Do we look like the Make A Wish Foundation to you? I'm not riding on a short bus to Homecoming!" (Skyler's callous refusal to allow Grace and Ben to join their Homecoming group)
- (Quinn: "It's actually really cool of Cara to draw these up for us.") I know, right? I kinda feel bad about what we're about to do. (Quinn: "Really?") No! I mean, who does she think she is ruining my entire senior year? She's here for like, what, two days and changes up the entire group? And now we're going with not just one, but two....retards...in our Homecoming group! It's humiliating, and she should know better." (Skyler's callous justification for her plot to prank Grace and frame Cara)