Pam the Pillow (ex-girlfriend)
Pam is a pillow that Jay routinely has sex with. She was introduced in “Pillow Talk”. In that episode, Jay believes that he impregnated her, which is a problem because he is thirteen years old, while she is forty. Pam expresses concern at his age, but Jay assures her that he’s willing to take care of their son, whom he names Scorpion. Scorpion is born with a trucker hat that has a weed symbol on it. This causes Jay to doubt if he’s the father of the child. Pam then reveals that Jay’s brother, Kurt, is actually Scorpion's father. This does not deter Jay from willing to care for Scorpion. The guilt is too much for Pam to bear, however, so she leaves.
Her next appearance is in the season 2 episode “Am I Normal?”. Jay and Jessi stumble across her as they hitchhike. Pam tells Jay that she misses him, and that the truck driver uses her for lumbar support, much to her horror. She and Jessi don’t get along, with the former accusing the latter of being jealous. She and Jay recount the good times they had together. Jay makes her promise to take good care of Scorpion.
Jessi Glaser (ex-girlfriend)
Jay has had a crush on Jessi for some time in season 1, and has been flirting with her since at least “Girls Are Horny Too”, with her often expressing annoyance at his crude personality. In “The Head Push”, Jessi french kisses Jay after drinking some Cotton Candy Brandy. She makes him promise not to tell anyone about their kiss. The two officially begin dating in “I Survived Jessi's Bat Mitzvah”. In “The Pornscape”, Jessi, fed up with her parents fighting, decides to run away and elope with Jay. The pair are then seen hitchhiking in the season 2 premiere. During their trip, Jessi ends up meeting Pam. Jessi then becomes disgusted upon learning about Jay’s sexual relationship with his pillow. This is when she begins to doubt their relationship.
The moment that broke the camel’s back for her was when they were making out in a motel, and Jay wanted her to engage in his fantasy where he is a forty year old magician and she is presumably thirteen. This thoroughly disturbs her and they have a fight about it, Connie further worsens Jessi’s fears about the relationship by telling her that she’ll end up as “one of those weak women who goes for bad guys with stupid brains and garbage dicks!”. All of this prompts her to break up with Jay, and the feeling is mutual. When Andrew and Nick find out about their breakup in “What Is It About Boobs?”, Jay calls it “fake news”.
Despite having entered a relationship with him, Jessi was hesitant to be known as Jay’s girlfriend, whereas Jay, on the other hand, wanted to introduce her as his “very serious girlfriend“ right away.
Suzette the Pillow (ex-girlfriend)
Jay meets Suzette in the season 2 episode “Am I Normal?”, at the motel where he and Jessi stay at. After he fights with Jessi not wanting to participate in his fantasy, a group of motel pillows immediately begin seducing him. One of them, Suzette, assures him that because they’re motel pillows “[they’re] down for anything”, which intrigues Jay. Suzette’s next appearance is in “The Department of Puberty”, where she confronts Jay about cheating on her with Brad. She questions his sexuality and demands that Jay get rid of Brad. Eventually, she takes a liking to Brad and ends up having relations with both of them.
In “My Furry Valentine”, Jay celebrates the holiday with them. Personality-wise, Suzette is classy, and her dates with Jay involve a fancy dinner, with her complimenting his magical prowess. Jay struggles with dividing his attention between Suzette and Brad. The pressure becomes too much for him, and he gets rid of them with a magic trick, stating that he needs to take a sex break in order to “collect [his] thoughts and figure out who the fuck [he is]”, thus ending his relationship with them.
Unlike with Jessi, Jay hadn’t interacted much with Matthew prior to their relationship. When he did, it was mostly to trade insults. The first instance of Matthew’s attraction to Jay was in “Requiem for a Wet Dream”, where the former described the latter as a “sexy Neanderthal”. Because he believed himself to be straight, Jay did not give any previous indication that he liked Matthew.
This all changed in “Smooch or Share”. At the class sleepover, Nick, Andrew, Missy, Jay, Devin and DeVon decided to play Smooch or Share, a combination of Truth or Dare and Spin the bottle. The game took place in the teacher’s lounge, where Matthew happened to be. On Jay’s turn, the bottle lands on Matthew. Matthew assumes that Jay doesn’t want to kiss him because he’s a boy. Jay clarifies that Matthew’s gender doesn’t have to do with it; he doesn’t want to kiss Matthew because he hurt his feelings. Jay ends up briefly kissing him anyway to avoid being burnt by coffee as per the game’s rules.
Later, after the kids banish The Shame Wizard and go wild, Jay and Matthew sneak off to the bleachers. Jay confesses that Matthew was his first “guy kiss” and confirms that he liked it. In turn, Matthew admits that Jay was his first kiss. Jay then initiates a second kiss that’s really more of a make out session. In “The Department of Puberty”, Jay approaches Matthew at his locker to discuss their relationship. Jay denies that their kiss meant anything to him. Matthew assures him that it’s a “one time thing”. He also makes a comment that implies that he believes Jay is in denial of his sexuality. Throughout this conversation, Jay is uncharacteristically flustered. This encounter eventually leads him to explore his sexuality with Brad the couch cushion. After some reassurance from Coach Steve, Jay accepts his attraction to Brad, and by extension, guys in general. It isn’t until “Cellsea”, in season 3, that Jay would identify as bisexual.
While Matthew has dismissed any interest in Jay, it is unclear if Jay has feelings for him.
Brad the Couch Cushion (ex-boyfriend)
Brad doesn’t appear to Jay until “The Department of Puberty”, after Jay made out with Matthew. Jay essentially uses Brad to explore his sexual attraction to other guys. This upset Suzette, who accuses Jay of being gay, to which he denies, since he still likes her. Eventually, Suzette warms up to Brad and Jay commences a relationship with both of them.
In “My Furry Valentine”, Jay celebrates the holiday with them. Personality-wise, Brad is athletic, and his dates with Jay involve hitting up the gym. Jay struggles with dividing his attention between Suzette and Brad. The pressure becomes too much for him, and he gets rid of them with a magic trick, stating that he needs to take a sex break in order to “collect [his] thoughts and figure out who the fuck [he is]”, thus ending his relationship with them.