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. Stacey returns home for the weekend, and even though she’s in a relationship, heats things up with her high school boyfriend, Mikey.

Jill proposes a way she and Jimmy can get back together in the weeks before Jimmy is set to leave, while Stacey and Mikey start sleeping with each other, rekindling their old flame. Pags is stressed when his recently divorced mother starts dating Stacey’s father, Mr. Ross, notorious for his cheesy commercials promoting his local electronics store.

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 (Sam Vartholomeos) stresses about finding Jill (Caitlin Stasey) the perfect birthday gift, a development in Jill’s professional life may ruin her special day. Meanwhile, Pags (Brian Muller) gets big news about his future, and things come to a head with Mikey (Jan Luis Castellanos), Tammy (Gigi Zumbado) and Stacey (Isabella Farrell).

As Jimmy (Sam Vartholomeos) counts down the days before he leaves for Alaska, Jill (Caitlin Stasey) proposes a romantic week away at her family’s lake house. After receiving the disappointing news about law school, Pags (Brian Muller) tries to salvage his relationship with Julianna while also pursuing a new business opportunity.