Jazz tells her parents she wants gender confirmation surgery before she finishes high school, but learns there may be obstacles along the way. Meanwhile, Jeanette struggles with the reality of the twins going off to college.

A bottom surgery consultation forces Jazz and her parents to process a troubling diagnosis. Meanwhile, Jazz confronts her friend Mya's brother, who's struggling to accept his sister's transition; and Jazz unwittingly finds herself on a date with a transgender boy.

Jazz goes to Pennsylvania to explore more options for her bottom surgery. Meanwhile, Jazz and Jeanette agree to participate in Grandpa Jack's presentation on transgender issues, but worry they may be confronted by hate like at last year's town hall.

While Jazz continues the search for a doctor to perform her dream bottom surgery, tensions flair as she battles with Jeanette over going to therapy to deal with her social anxieties. Meanwhile, the family plans huge surprises for Jazz's upcoming sweet 16.

Jazz leaves her comfort zone and tries "Dating in the Dark," and hopes it's a good way to get to know someone before revealing she's transgender. Meanwhile, Jazz and her parents attend a pride parade and meet a survivor of the Orlando nightclub shooting in 2016.

Jazz helps her transgender friend Lynn deal with bullying from her own mother; Jeanette struggles with the medical decisions Jazz is facing and decides to go to a support group; Jazz hopes for a call from the boy she met at Dating in the Dark.

After three bottom surgery consultations and no clear path forward, Jazz and the family head to San Francisco hoping a final consultation will give them good news; Jazz takes on conservative host and transgender bathroom rights critic Tomi Lahren.