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.