|“||It only counts if you saw a nipple.||”|
Although he does seems to be Gretchen's boyfriend, he does go to the Old Orchard Mall and Cady's get-together with Taylor Wedell. Karen Smith says he does this to make Gretchen jealous. Jason was seen making out with Gretchen in Cady’s bathroom.
On the very first day of this school year, Jason encounters Cady, jokingly asking her if her 'muffin is buttered'. This annoyed Regina, who told him he's a skeez, that he should go home and shave his back.
Jason later appeared in the audience of the Winter Talent Show, where he, along with his friends, made fun of Damian's performance. After the Plastics took the stage and performed their signature Jingle Bell Rock dance, Gretchen accidentally kicked the radio into his face.
Jason has also said that Cady might even be hotter than Regina.