Diary of a Teenage Girl Books in Order

Sixteen-year-old Caitlin O'Conner records struggles with family, friendships, school, and romance in her diary. As she questions who she wants to become, her growing interest in Christian faith changes how she approaches teenage life.

Caitlin O'Conner starts a summer job and prepares for a church mission trip to Mexico. Her new faith commitments compete with loyalty to her pregnant best friend, Beanie, as she weighs friendship, romance, and responsibility.

Caitlin O'Conner begins college hoping for a fresh start, but her roommate's behavior challenges her Christian convictions. Homesickness and difficulty fitting into campus fellowship leave her questioning where she belongs as she tries to build an independent life.

During her senior year, Caitlin O'Conner weighs a mission trip to Mexico against her parents' college plans. Questions about romance and misunderstandings surrounding Beanie's relationship with an African American boyfriend challenge Caitlin's faith, friendships, and understanding of prejudice.

Freshman Chloe Miller resists pressure to fit in while searching for an identity and questioning faith. Josh's younger sister channels her interest in music into an all-girl Christian band called Redemption, bringing her beliefs into school and friendships.

Chloe Miller's band Redemption wins a recording contract and tours with Iron Cross. Life on the road brings exhausting demands, while Laura's increasingly strange behavior leaves Chloe worried that her bandmate may be using drugs.

As Redemption attracts attention, Chloe Miller must distinguish genuine friends from people drawn to the band's success. A Nashville scout offers new possibilities, but music, school, family, and misplaced generosity complicate her growing confidence.

Chloe Miller and her Redemption bandmates juggle school, friendships, and a demanding music career. A crush on Iron Cross's lead singer and the responsibilities of their Christian ministry complicate Chloe's efforts to keep her priorities straight.

Caitlin O'Conner accepts Josh Miller's proposal and begins planning their wedding during her final college year. Family expectations, money, and friends' troubles complicate preparations as she considers what her faith means for the marriage ahead.

After a speeding ticket, Kim Peterson writes an anonymous advice column for her father's newspaper to regain driving privileges. Answering other teenagers' questions forces her to confront her own uncertainties about faith, identity, and life's meaning.

Kim Peterson struggles to understand faith while her mother faces advanced ovarian cancer. Her friend Natalie's prayers and her developing relationship with Matthew bring further questions about belief, intimacy, and the choices she wants to make.

Following her mother's death, Kim Peterson faces her father's job loss, family arguments, uncertainty about Matthew, and Natalie's pregnancy. These overlapping troubles test her faith as she searches for stability in a life that keeps changing.

Kim Peterson's senior year brings a friend's pregnancy, a letter from her birth mother in Korea and questions about taking in a cousin. Still grieving her mother, Kim must weigh family responsibilities and difficult advice against her developing faith.

Fifteen-year-old Maya Stark's glamorous life hides isolation and her mother's drug use. When her savings disappear and her mother faces prison, Maya moves in with relatives, forcing her to reconsider independence, identity and where she might belong.

Maya Stark's summer brings a job, boyfriend, and hybrid car, along with an opportunity to write an environmental newspaper column. She tries to reconcile her commitment to living green with Christian faith and difficult youth-group relationships.

Maya Stark considers early graduation while a hostile cheerleader, misunderstandings with her ex-boyfriend, and her mother's coming prison release complicate her life. Unexpected musical opportunities force her to weigh ordinary teenage life against a more glamorous future.