On one awful day, Princess Carolyn deals with rejection, deception and loss. BoJack and Diane try to track down Hollyhock's birth certificate.
In the distant future, a cat girl named Ruthie is giving a presentation on her ancestor Princess Carolyn on a specific day.
It starts out in the morning where Princess Carolyn is very happy with her situation; a caring boyfriend, a baby on the way, and a high-end client.
Ralph allows her to have a little sip of coffee, but Princess Carolyn accidentally spills it on her clothes and breaks her necklace.
Ruthie then informs her class that this particular day would suck.
Princess Carolyn plans on getting Courtney Portnoy another acting gig in a movie called Corpse Me If You Can-Can, but this turns out to be a set up as Courtney fires her as manager for the failures of Miss Taken and her and Todd's sham wedding. Determined not to let this get her down, she calls up Mr. Peanutbutter for a possible new acting gig, but Peanutbutter tells her he's busy helping Woodchuck on the election against Jessica Biel and Katrina.
Meanwhile, BoJack has decided to go to the courthouse of Hollywoo to find Hollyhock's birth certificate and brings Diane along as Hollyhock is too busy "counting her teeth". Their efforts turn fruitless, however, as BoJack gets fed up with the long lines and paperwork, and they leave empty-handed.
Princess Carolyn goes to a jewelry store to get her necklace fixed.
Ruthie explains Princess Carolyn’s necklace was a priceless family heirloom from the old country, the one item her grandmother refused to sell despite the family's extremely poor conditions, so that she could pass it down to her descendants to remind them that they came from generations of strong women who always landed on her feet.
While at the jewelry store, Princess Carolyn meets up with Charley Witherspoon, who mentions to her about the offer he made last year to merge companies, but Judah told him she wasn't interested, surprising her. She tries to get Judah to confess to it, but he does not confirm about the situation.
Princess Carolyn, heads over to the doctor's office for a check up on the baby, but unfortunately she had another miscarriage, and the doctor informs her it isn’t likely she’ll get pregnant again.
Her day gets even worse when she finds out her necklace, which she believed to be a family heirloom since her grandmother, turns out to be a fake costume jewelry necklace from JC Penny.After she gets in her car, Princess Carolyn finally breaks down crying. However, she is forced to collect herself when Ralph calls. She lies and tells him everything is ok. Ralph tells her she’s so easy.
At the office, Princess Carolyn starts drinking alcohol when Judah comes in. She confronts him about the offer Charley made, and Judah admits that he was only trying to protect her. Princess Carolyn, however, is angry that he lied to her, and fires him as her assistant.
Princess Carolyn later goes to dinner with Ralph, but is very reluctant to tell him about the miscarriage, eventually deciding to leave after hearing the waiter greeting clients named "miss Carey" or "miss Carrie" and awfully sounding like "miscarriage".
Instead of going to Ralph's place, she returns to her old apartment, only to see Todd's horrifying Clown Dentist practice at work.
Later that night, she drinks heavily at a party with Todd and the clowns when Ralph comes over. An argument happens with Princess Carolyn revealing the miscarriage, and adding in the reveal that this is the fifth one she had throughout her life.
While Ralph wants to try and look for other options to have a baby, Princess Carolyn, feeling as if she failed being his "easy" girlfriend and refuses to give up on trying to get pregnant herself, breaks up with him.
Princess Carolyn goes back to the office when BoJack calls her about the terrible day he had. Princess Carolyn, who herself had possibly the worst day of her life, tells him that whenever she has a bad day she imagines that her future descendant is talking about her in class.
While BoJack points out that all of that is fake, she sadly notes that it makes her feel better.
- Princess Carolyn has another miscarriage, and it’s very unlikely she will be able to get pregnant again.
- Princess Carolyn and Ralph break up.