On the night of his college graduation, Jimmy falls back into the arms of his ex-girlfriend Jill, much to the concern of his friends and parents who worry restarting this relationship may derail his future plans as a nature photographer.
Jill proposes a way she and Jimmy can get back together in the weeks before Jimmy is set to leave, while Stacey and Mikey rekindle their old flame. Pags is stressed when his recently divorced mother starts dating Stacey’s father.
After breaking up with Jill, Jimmy finds inspiration in a different style of photography, while Artie is dreading Jimmy’s departure for Alaska. Meanwhile, Stacey suspects Mikey may have eyes for Tammy, while Jill battles her overbearing mother Lana.
Jill and Jimmy decide to be chaperones on a blind date for Pags, hoping they can just be friends. With Stacey back in the city, Mikey and Tammy make a plan.
While Jimmy stresses about finding Jill the perfect birthday gift, a development in Jill’s professional life may ruin her special day. Meanwhile, Pags gets big news about his future, and things come to a head with Mikey, Tammy and Stacey.
As Jimmy counts down the days before he leaves for Alaska, Jill proposes a romantic week away. After receiving news about law school, Pags tries to salvage his relationship with Julianna while also pursuing a new business opportunity.
Jimmy and Jill brace for an awkward reunion. Pags looks to Tammy to help his sister’s band find a drummer for their big concert. Stacey has issues with Jill’s new, married boyfriend.
Stacy scores a big audition for a Broadway show, only to be hit on by the director. After his parents demand he make life changes, Mikey decides to propose to Tammy. Artie’s plans of a father-son project may be in jeopardy with Jimmy’s work opportunity.
When Jimmy introduces his family to Maya, an unexpected development upends Jimmy’s future. Jill celebrates her birthday with Henry, who dazzles her with a night to remember. Meanwhile, Stacey gives Luke a second chance.
Pags tries to convince Tammy to join Wildfire as record labels show interest. Mr. Ross attempts to make peace between Jill and Stacey. Maya gives Jimmy disappointing news, while sparks fly between him and Jill. Mikey jumps back into the dating game.
Jimmy has an encounter with Jill, who has a big interview with a prominent fashion designer. Pags’ jealous streak causes trouble when Julianna gets an opportunity to work with her ex. Genie auditions a new song she hopes to perform for Wildfire.
Jimmy and Jill are unsettled about the future, especially when Jill gets a new opportunity. There’s a major rift in the band, for which Tammy thinks she understands the real reason. Stacey has the biggest audition of her life.
