Cassie sets up her sister with the most eligible bachelor on campus while Taylor enlists Tony's help to break a forbidden family taboo, despite Robert's questioning.
Robert recruits Tony's help to find a beautiful actress on campus for his latest student film. Rob agrees to a group date with Cassie's sister despite their differences.
Cassie reconnects with an old boyfriend while Rob and the baseball team concoct a plan to change their negative image on the university grounds. Against Robert's advice, Tony signs up for every club on campus except the one Robert is leading.
Cassie's boyfriend isn't impressed with Cassie's latest photo shoot in Vegas and speaks his mind. Rob takes Tony on an adventure in the tunnels under campus not realizing it will bring Tony face to face with his greatest fear.
Rob and Hannah meet on the baseball field where they both experience a mutual, first date. Robert turns the heat up on Tony challenging him to extreme adventure on campus. Cassie asks Taylor to take a leap of faith.
Tony enlists Cassie in his latest prank outside the girl's dorm. Rob wakes up to find his treasured Mustang GT shrink-wrapped while Steve courts Hannah in the library.
While on a self imposed fast of all social media and humour, Tony meets his match on a blind date with hysterical consequences. Cassie and Caelan's relationship reaches new heights when they go skydiving.
Calean has to decide between a great opportunity overseas and his relationship with Cassie. In a haphazard camping trip, Rob & Steve talk about life, love and Hannah. Emily convinces Tony to go underground and conquer his greatest fear.
They're young, Christian and questioning their next move in life and love. Michelle confronts Cassie about her sister's unresolved feelings for her ex-boyfriend Caelan. Tony looks for advice from Robert about his crushing student debt that is holding him back from a proposal. And when Caelan and Cassie's date doesn't go as planned, moving on becomes harder than they both expected.
Caelan and Cassie's conversation ends with an abrupt exit. Later Caelan looks to his best friend Andre for some clarity about his feelings. Cassie's family has as hard time ending their communication with Caelan. Meanwhile, Tony, with the help of his friends (and some goats) tries selling t-shirts to earn money for an engagement ring.
Cassie and Caelan wonder if their romantic past prevents them from just being friends. Robert uses his unique movie-making style to help with a special project. Will Cassie listen to her sister's advice about moving on from Caelan?
During a cabin getaway, Cassie and Kendall open up about their unspoken tension and feelings for Caelan. After Tony gushes about his girlfriend, he asks Cassie what she is looking for in a partner. And will Tony's "Catastrofee" t-shirt finally take off?
Tony's job search brings him to the Randolph home. Caelan is forced to rehash his feelings for Cassie, and who will show up to Tony and Caelan's Lil' Ballers basketball camp?
In the season 2 finale, can Caelan take an important step to bring closure to his relationship with Cassie? Will Tony need to move back to Alaska and put his engagement hopes on hold?