SpongeBob wakes up, stubs his toe, and starts crying. He rips his favorite shirt and starts crying again. He goes downstairs and hears a sad song on the radio, he cries again. At work, he flips a Krabby Patty, which lands on the ground when, SpongeBob until over again golden patties. Mr. Krabs startles him. SpongeBob then cries once again. Squidward gets irritated of SpongeBob's crying and he yells at him. SpongeBob then cries. Sponge bob says "You yelled at me".Squidward tells SpongeBob that he cries too much, SpongeBob denies it. Squidward then pulls up a TV and plays a video of a trillion tears and millions of places where SpongeBob has cried over those years. He then makes a bet with SpongeBob that he couldn't last until midnight without crying. After the bet is made, Squidward follows SpongeBob home to make sure he cries, and tries to make SpongeBob cry over things like a beautiful sunset, sad news stories, sad news stories with funerals, a sad song on the clarinet, and a sad bedtime story. Amazingly, SpongeBob manages to hold in his tears until midnight, despite all of Squidward's best attempts, and after midnight, SpongeBob cries all over Bikini Bottom like crazy. Squidward comes over for a slumber party the next night, and the episode ends with Squidward crying and screaming and SpongeBob comforting him.
The title card is identical to Pickles, but it is a bit zoomed-in more.
Squidward's line "I just threw up in my mouth a little," is a reference to the movie Dodgeball: A True Underdog Story.
On the radio, if you listen carefully, the announcer said the song was by Eely Dan. This is an obvious reference to the jazz rock band Steely Dan. Also the next song was by Lionel Fishy. This is also a reference to Lionel Richie.
The radio announcer also states that the song's name before "Sad Songs" was Aja, a song by Steely Dan on the album of the same name and a song called "Sad Song" by Paul Williams.
During the slideshow Squidward made of SpongeBob's breakdowns over the years, SpongeBob wore his Krusty Krab hat in all of the clips even though most weren't set at The Krusty Krab.
This means that Squidward might have made the slideshow up.
The Bikini Bottom Men's Choir made another appearance in this episode.
Drama Link O - "And finally, sad news for Mermaid Man & Barnacle Boy fans. They will only be showing the Mermaid Man & Barnacle Boy episodes 7 times a day, instead of 8 ..." (then SpongeBob changes the channel)