Tibby Rollins

Family

Tibby's parents are described as former hippies. She was born when they were 19, and she apparently spent much of her early life swept up in their various adventures; her father was, at turns, a writer for a socialist newspaper, a public defender, and an organic farmer, while her mother was a sculptor. Eventually, her mother became a real estate agent and her father became a corporate lawyer. They settled down in a suburban house with Tibby and her two younger siblings, Nicky and Katherine, who are respectively thirteen and fourteen years younger than her. Tibby often feels like an outcast in her own family, viewing herself as a leftover of her parents' former life. As a result, she resents her younger siblings and tries to distance herself from them during the first two novels.

Friends

Tibby's best friends are Lena Kaligaris, Carmen Lowell, and Bridget Vreeland. She has known them all since birth. She also befriends Bailey Graffman and has a guinea pig Mimi who both die at the end of the first novel.

The Sisterhood of the Traveling Pants

Stuck at home in Bethesda, Maryland while her three friends went to Greece, Mexico and South Carolina, she decides to make a "suckumentary" about people she considers to be "lame," among them her coworkers at Wallman's and Brian McBrian, a fellow high schooler who spends most of his time playing Dragon Master at the local 7-Eleven. At Wallman's, Tibby meets twelve-year-old Bailey Graffman, who is dying of leukemia and is eager to help Tibby with her movie. Bailey, afraid of not having enough time to truly understand people and, in turn, be understood, looks beyond appearances and finds the true worth in each of Tibby's documentary subjects, allowing Tibby to do the same. Bailey dies at the end of the novel and Tibby decided to make the documentary about the summer she had with Bailey

The Second Summer of the Sisterhood

Tibby takes a course in filmmaking at Williamston College. She tries desperately to impress Alex and Maura, two of her classmates. In the process, she ends up shunning Brian (who has become one of her closest friends since the end of the first novel) when he visits her and makes a video which upsets her mother. In the end, she realises that Brian is her true friend, and Alex and Maura are phony. She makes a touching video about Bailey, and Brian and her mother forgive her.

Girls in Pants: The Third Summer of the Sisterhood

Brian asks Tibby to the senior dance at their high school, and she says yes. After the dance, at a picnic table, they exchange their first kiss, and Brian reveals his feelings for her. The next morning while thinking about Brian, Tibby forgets that her younger sister has been trying to get an apple from a tree outside her window. She opens the window, and her sister accidentally falls out. Tibby becomes depressed and blames herself, so she avoids Brian.

Eventually, though, she comes to terms with her problems. Tibby ends up helping deliver Carmen's half-brother, Ryan and becomes his godmother. After that, she finds Brian, and together, they strip off their clothes and jump into the city pool, marking their start as a couple.

Forever in Blue: The Fourth Summer of the Sisterhood

Brian, Tibby's now long-term boyfriend, visits her and announces that he's been admitted to NYU, where she studies. Afterwards, they get drunk and have sex for the very first time. They discover that the condom broke, leading Tibby to suspect that she may be pregnant. Although she later finds out that she is not, she breaks up with Brian. Lena's younger sister, Effie, then seeks her out and asks her permission to go out with Brian.

Tibby begins to doubt her decision to break up with Brian and becomes terribly upset. Lena then goes to Tibby's house to comfort her. They talk about their relationships and both come to a revelation, that they only fall in love once. Tibby meets Brian at the site of their first kiss, the picnic table, and apologizes for letting her fear ruin their relationship. They enter a new stage in their romance. This results in Effie taking the pants out of anger, and accidentally losing them in Greece.

Sisterhood Everlasting

Ten years following the last sisterhood book, Tibby has moved to Australia with Brian and now has almost no contact with the three other girls. Soon after moving to Australia, Tibby learns that she is not only pregnant but she is also diagnosed with a terminal disease. She keeps the pregnancy a secret from the sisterhood and her family, as revealing it will also reveal the disease. Nearly two years after giving birth to her daughter, Bailey, she calls her "sisters" together for one last trip to Greece. Disaster strikes when she suddenly dies in a swimming accident on the shores in Greece leaving her sisters, Lena, Bridget, and Carmen, devastated and assuming that she had taken her own life.

It is revealed through the novel that Tibby was suffering from Huntington's Disease and aware that she was going to die, even though her death by drowning was an accident. When she invited the girls to Greece she was going to reveal this and give them letters to help them move on. It is later revealed that she discovered she had the disease when she found she was pregnant with her daughter Bailey. Her final gift to Lena, Carmen, and Bridget is willing them to move on because life is too short.