Tear Jerker / Superstore

• In "Back to Work", Cheyenne (while still on leave) comes in to buy groceries and share pictures of baby Harmonica. The usual antics prevent her from sharing the pictures much, which isn't too bad but does make her feel like her coworkers haven't missed her. The real bad part starts when she tries to sneak her stuff through a register in order to skip the line and is too meek to walk away when other customers starting having her cash them out as well. She tries to sing to her daughter over her cell, but a customer snaps at her to hang up and in a panic, she accidentally packs her phone in his bag. By the end of the episode, she can still be seen stuck at the register and hasn't once been noticed by any of her colleagues.
• At the end of "Lost and Found", Amy confesses to Glenn that her home life is failing because she and her husband realized they were both unhappy with their marriage and their daughter is upset by the situation.
• Mateo saying that he doesn't love Jeff. Poor Jeff and Mateo are both clearly hit hard by it. Even worse is that Mateo only said it to avoid outing himself as an illegal immigrant. He tries to call Jeff during the tornado when he thinks he might be dying, but never gets through.
• Glenn desperately asking Jeff to not make him fire employees who Glenn thinks of as family.
• "Lottery":
  • Poor Myrtle, after being fired from Cloud 9, is stuck collecting cans late at night to make measly profits and spending her nights in cheap motels. She's so happy when Glenn offers her thirty dollars, and Glenn just looks horribly guilty for firing her.
  • At the end of the episode, Amy and Jonah stay out late at the golf course. It's a sweet moment... but not for Kelly, who's trying to call Jonah about the evening together he'd promised her, but isn't getting any response. Then she gets locked in the store and is left all alone.
• Sandra being forced to break up with her boyfriend... all because she lost at a coin toss. Even worse in that they were in the middle of moving in together.
  • And prior to that, she goes on a rant about how she deserves happiness because the universe craps on her so much. Way to Kick the Dog.
• You wouldn't think you'd feel terrible for Marcus, until mid-season 4 when Mateo accidentally finds him living in the back passageway of the store. As it turns out, Marcus has been homeless for some time, and the poor guy looks humbled and humiliated at being caught, leading Mateo to be his Secret-Keeper.
• "Lovebirds," when thanks to a stupid move by Garrett, all of Dina's birds escape their cages and fly out of the store, never to return, and Dina can't run fast enough to do a damn thing about it.
  Dina: Don't let them get away! Come back!!! Lock all the doors, please!!! MY BABIIIIIIES!!!
• "Employee Appreciation Day" ends with Mateo being taken into ICE custody while all the store employees look on sadly. What's worse is that just before this, he is trying to escape the store with Amy and Cheyenne while Dina tries to find them a safe exit. When they realize they are going to be surrounded by agents, Dina regretfully tells them she is sorry while Mateo gives up and allows himself to be taken.
• "Myrtle" is already sad enough given the titular character's passing (much like her actress), but then you add the subplot of Dina finally seeing her Disappeared Dad again and mending their relationship, only for him to blow it with an incredibly hurtful comment — specifically, remarking that it was probably a good thing that he left her since it made her a stronger person. The aftermath is the most vulnerable Dina has been up till this point, and it is gutting.
• "California: Part 2":
  • Amy and Jonah break up prior to her moving to California since she isn't totally ready to get serious with him to the point of marriage. Their final scene together is just them quietly toasting one another from a distance as the other employees watch fireworks.
  • Glenn and Amy have a heartfelt goodbye in Amy's office, crying over the fact they won't see each other every day after decades of working together. They want to hug each other, but due to social distancing, they can only hug themselves.
• "All Sales Final."
  • The entire closing of the store. Despite everything the staff did over the years, despite everything they went through, it still wasn't enough and the majority of them are out of a job.
  • Since her departure, Amy has come to realize that turning down Jonah's marriage proposal was the biggest mistake of her life. However, there's no easy reconciliation right away, as even after Amy tells Jonah this, he still is reluctant to get back together due to how incredibly hurt he was by her rejection.