"Pilot": When Troy meets Jeff, he calls him "Seacrest" and indicates since Jeff says he is a Spanish tutor, that Jeff can do all his homework for him. In order to calm the study group down, Jeff compliments them all including saying to Troy that astronauts want to impress their high school prom king. Later, Troy is impressed with Jeff's answer to Troy's dilemma on whether to wear his high school letterman jacket or not.
"Spanish 101": Troy is excited to see Jeff enter the study room and greets him with "word them up!".
"Introduction to Film": Jeff convinces a number of those in the study group to join him in Professor Whitman's "easy A" class including Troy. In his first day in class, after seeing how easy it is Troy reaches out to Jeff for a fist bump. Jeff reciprocates but says "never again". Later, when Jeff catches Troy and Abed dancing in the study room, Troy says they are krumping. Jeff disagrees and shows them how it is done.
"Social Psychology": Troy calls Jeff "Doctor Doogie Seacrest" and that he thinks he is better than everyone else because he is 40 when he and Abed are making fun of students outside the study room not knowing they can hear them. Jeff says he isn’t 40, that everyone can hear their insults and calls them morons.
"Football, Feminism and You": Initially, Jeff supports Troy in turning down an opportunity to play quarterback for the Greendale football team. However, after the Dean puts Jeff on the college recruiting posters, Jeff convinces Troy to play in order for the posters not to be used. This causes a conflict with Annie which makes Jeff feel guilty. He tries to get Troy to quit football at a pep rally but Troy is OK playing because the standards at Greendale are so low there is no pressure on him. Troy passes wisdom to Jeff by saying he should accept he is at Greendale and relax.
"Introduction to Statistics": Troy asks Jeff to leave the faculty Halloween party to help Pierce and then acknowledges Professor Michelle Slater as "pretty hot". Later, he catches Jeff with Slater in front of Borchert Hall and gets him to save Pierce from his fort of chairs.
"Home Economics": When Jeff is kicked out of his condo, Troy says he'd offer for Jeff to stay at his place but his Dad is kind of racist.
"Environmental Science": The study group tries to get Jeff to talk to Chang about easing up on homework. Jeff dissuades them but it is Troy who points out Jeff is convincing and gets him to relent. When the group finds out Jeff is partying with Chang to get good grades for himself only, Troy says Jeff has a weird forehead.
"Comparative Religion": Troy helps Jeff get ready for a fight with school bully Mike Chilada by teaching him the Forrest Whitaker stare and "what's up?".
"Romantic Expressionism": Jeff tells Troy (in secret) a number of things about Annie to make Troy interested in her. After Troy blows his attempt to attract Annie, Troy yells at Jeff (and Britta). Later with the study group present, Troy says that Jeff got "weirdly specific" when describing Annie's body.
"Physical Education": When Abed does an impression of Jeff (with Jeff present), Troy compliments him on it. Troy then asks why Jeff isn't in billiards class which prompts an angry eruption from Jeff.