19-year-old Olive St. James is excited to be babysitting her little sister, 6-year-old Clementine. But Olive finds herself having to be the disciplinarian when Clementine disobeys Rachel’s instructions and then lies to Olive about it. Note: counting Jesse as a character because he appears in a flashback conversation.

Leah Healy has graduated high school, and assumes she had received all her gifts. But then her mother Becky surprises her with the best gift of all. Cw: death

Three part story. Jesse and Rachel had always known they had wanted a family of their own, but decided to wait a while after Rachel gave birth to Kurt and Blaine’s daughter, Maya. However, things don’t always go according to plan.

Sequel to “Annie St. James.” Annie St. James, now 19, and her brother Jesse have been helping Jesse’s friend Tyler direct his original musical. They’re as close as they’ve ever been but then Annie makes a request that surprises Jesse. Cw: mentions of addiction, eating disorder and also (likely) some language.

6-year-old Olive St. James is having Grandma Day at her school and she’s not looking forward to it, as she doesn’t have anyone to take her.

14-year-old Olive St. James is excited to be cast as the lead in the school play. Even more exciting is that her half-sister Maya Hummel-Anderson, 15, will be doing stage crew and they’ll get to spend a lot of time together. But soon, it becomes apparent that someone wants to stop the show from opening. It’s up to Olive and Maya to find the culprit and save the show.

Maya Hummel-Anderson is spending the weekend with her biological mother Rachel, as well as Rachel’s husband Jesse and their daughter Olive. When Maya asks Rachel for help with a school assignment, she wonders why Rachel gets so upset after reading her essay. Cw: death

16-year-old Olive St. James is excited to do a theatre workshop led by none other than her mother, Rachel. However, she soon realizes that being the teacher’s kid is not all it’s cracked up to be.

Jesse and Rachel have some exciting news for Jesse’s little sister, Annie. T for some language, implication of sex. Also Cw for mentions of addiction/eating disorders. Playing around with the concept of the Annieverse and Oliverse being one AU. Enjoy!

Holden is surprised and dismayed when his mother, who he hasn’t talked to in months, invites Holden, his younger sister Mary (OC), and their significant others for dinner one evening. After the disaster that was Debbie meeting Mary, Holden is not optimistic about the gathering. Cw: language and reference to pregnancy loss.

AU where Mark and Becky had a daughter Leah. While Jackie is babysitting her great nieces Leah, 11 and Harris, 4 - she wants them to make Father’s Day cards. Leah gets upset, as her dad has just recently passed away. Cw: death of a parent

Rachel is out of town, which means Jesse gets to spend some quality time with their 12-year-old daughter, Olive. But during that time, Olive experiences a pretty big change, something her mom would be much better equipped to help her with. Jesse just wants to support Olive in any way he can. Can he figure out how to do that?

Jesse and Rachel have some news to tell their 13-year-old daughter Olive but they’re not sure how she’ll take it. Rated T just in case (sex references and possibly some language)

AU where Wendla doesn't get an abortion and has her and Melchior's daughter, Ada Lise Gabor. Wendla wants to tell the almost four-year-old Ada the truth about Melchior Gabor, the man who she sometimes gets to visit and play with, but pressure from her bitter mother, as well as the fact the couple remains unmarried, weigh heavily on her mind.

Kurt and Blaine want to go on vacation, so Rachel suggests that their daughter Maya, conceived with Rachel’s egg donation, spend that time at the St. James' house so she can bond with her half-sister Olive (Rachel’s daughter with Jesse) despite their history of not getting along.

A collection of snippets from the life of Jesse’s little sister. Annie, like her brother, is also a performer and is tired of living in her brother’s shadow. Cw: addiction, eating disorders, and car accident death. May add additional characters from the show besides Jesse. Enjoy!

*I’ve never written a fic like this before so bear with me* Rachel forgave her husband years ago for the egg incident, but can’t help but think how easily he got off. She knows the perfect punishment, but it’s a bit old-school. Awkward chaos ensues. Consensual spanking between two adults occurs so do with that information what you will. Some swearing as well.

Leah Healy is a big sister at 23 years old. Despite the multitude of events leading up to this moment or the rollercoaster of emotions she’s experiencing right she could not be more ready to take on this new role.

A collection of stories about Jesse's little sister, Annie, at various points in her life. Annie St. James is tired of living in her older brother's shadow and truly just wants his approval. Language. Also Cw: discussion of addiction, eating disorder, and death by car accident. May add additional characters from the show besides Jesse later on. Enjoy!

AU where we meet Holden's little sister, Mary. She's about ten years his junior and enjoys embarrassing her brother. This story will be a collection of moments where she and Holden interact, as well as her interactions with his colleagues and girlfriend. Enjoy! Cw: Language