The Pajama Diaries is a syndicated comic strip created in 2006 by Terri Libenson, an artist who has also done work for American Greetings. It is narrated by Jill Kaplan, a wife of a loving husband and working mom of two young girls in a Jewish family somewhere in Ohio done in real-time fashion, where the characters age with the progressive years of the series and deals with varying topics from the everyday silliness and dramas of life to social commentary. The Pajama Diaries is carried by King Features Syndicate.
- Jill Kaplan: The modern, multitasking mother of two girls and wife of Rob Kaplan. She is descended from Sephardi Jews. Jill works at home as a web designer, and often has to balance her job with her home life. She is an emotional type, and a bit of a self-confessed control freak, especially when it comes to her daughters. Every now and then, her teenaged subconscious voice of reason, or in certain cases, unreason, '80s Jill, appears in the bathroom mirror to voice her opinions. Often, 80s Jill brings along old friends from days gone by. Jill also has a brother, yet to be introduced, that lives out of state.
- Rob Kaplan: Jill's easy-going, yet bluntly honest husband, of Russian Jewish background, father to daughters Amy and Jess, and devoted to his family. He is a semi-independent IT contractor who works outside of home. If he has a fault, it is that he has a constant libido that sometimes Jill finds irritating.
- Amy Kaplan: The elder daughter of Rob and Jill. She is currently in junior high and just entering adolescence, and has become infatuated with Lisa Day's eldest son Danny. In the spring of 2013 she completed her bat mitzvah. She is set on being athletic, independent, and outdoing Jess. Amy acts as Jess' substitute parent when their Mom and Dad are debating whose turn it is to take care of them.
- Jess Kaplan: Amy's playful, gifted younger sister who's now a tween. She enjoys playing with dolls, watching TV, and listening to Hannah Montana. Jess acts as Amy's substitute parent when their parents are debating whose turn it is to take care of them.
- Lisa Day: Jill's best friend and the mother of three children: sons Danny and Noah, and third one yet to be identified. Early in the strip two of the children were named Matthew and Katie. Lisa has a struggling marriage and recently separated from her husband. In the fall of 2013, Lisa is studying to be a teacher and is a student teaching in Jess's school.
- Nanci Raymond: Jill's friend who is an assertive and ambitious mother of teenaged twins. Her current second marriage is to David, the elderly father of a former beau. In November 2013, she learned that she's pregnant with David's child.
- Grandma Sophie: Rob's old-fashioned Polish grandmother who enjoys reminding Jill about the virtues of being the ideal homemaker. Jill finds these reminders annoying. Grandma Sophie tells of leaving Poland when she was a little girl before World War II while the remainder of her family perished in the Holocaust. Every Yom Hashoah she lights a candle for them in their memory.
- "Perfectville": The "perfect" next door neighbours across the street from the Kaplans. They do everything right, seemingly without effort, from their pristine lawn to their always appropriate housewarming gifts. Perfectville refers mainly to the overachieving, African-American mother (real name is yet unknown). Despite her friendliness and well-meaning advice, Jill is both envious and amazed by her neighbour's ability to do it all and to do no wrong. In helping Jill to prepare for Amy's bat mitzvah party, Perfectville reveals she was once a CEO for an advertising agency until her firstborn came and she decided to give up the working world for motherhood, plus that she got fired for blowing a $2-million account of one of her former firm's clients and has recently launched her own party-planning business.
- Jill's Mom: A widowed retiree residing in Florida with her live-in companion, Harv at a retirement community. It is unclear whether the relationship is romantic or not. She often complains of the ailments related to old age to Jill with grotesque details.
- Deb Lowell: Another friend of Jill and working mother. Was part of her circle of friends early in the strip, but has not been seen since.
- Harper: A friend of Rob and a bachelor looking to settle down. Was part of the Kaplans' circle of friends earlier in the strip, but has not been seen since.
There are three books containing collections of The Pajama Diaries strips, including bonus strips. They are currently published by TJ Studios.
- The Pajama Diaries: Déjà To-Do! (2011) ISBN 978-0983327202
- The Pajama Diaries: Having It All...and No Time to Do It (2013) ISBN 978-0983327233
- The Pajama Diaries: Bat-Zilla (2013) ISBN 978-0983327264
Heaton, Michael (2009-03-23). "Ten Minutes with 'Pajama Diaries' cartoonist Terri Libenson". The Plain Dealer. http://www.cleveland.com/pdq/index.ssf/2009/03/ten_minutes_with_cartoonist_te.html. Retrieved 2009-03-27.