This page lists instances when characters have cried for one reason or another.
Episode
Reason
Take This Job and Squeeze It
Cried because she had to get a job to pay off her credit card debt.
The Big Sickie
Cried after poking herself in the eye with a mascara brush intentionally so that she could convincingly cry while telling a story about Jen's "aunt" being in the hospital.
A Lime to Party
Cried because Big Steve was about to move The Big Squeeze to a strip mall due to low sales.
The (Almost) Graduate
Cried because she got herself locked in the lemon and when Jonesy got the job she was dreaming about at Albatross & Finch .
Later in the episode, she cried again after remembering what happened.
The Khaki Girl
Cried when Tricia beat her out for the Khaki Girl title.
Cecil B. Delusioned
Cried after a boyfriend broke up with her.
Cried again because she wanted to get Nikki to submit to a makeover.
6teen: Dude of the Living Dead
Cried because her boyfriend got turned into a zombie and he stood her up when he asked her to prom.
Going Underground
Cried because she regretted breaking up with Talon .
Deadbeat Poets Society
Cried after being called "The Fart Girl."
Fish and Make Up
Cried when she and Nikki got into a fight, which ended with Nikki harshly saying that she and Caitlin aren't friends anymore.
Cried at Fish 's funeral, both because Jude's friend had died and because she was sorry about fighting with Nikki.
Major Unfaithfulness
Cried when she got a "red mullet" hairdo, and out of fear when she thought that her boyfriend was going to think that she cheated on him when she got a haircut from a different sylist .
Waiting to Ex-Sale
Cried when Tad broke up with her following a fight they had.
The Hunted
Cried when her date stood her up, only for her to learn that Nikki did it out of revenge.
The Lords of Malltown
Cried after breaking up with Billy .
Cried when she found out that she paid for Jen's date with Carl .
Smarten Up
Cried at the end of a romantic comedy.
Cried when Josh broke up with her.
Dirty Work
Cried when she found out that her new makeup wrecked her skin.
A Crime of Fashion
Cried when she was arrested after she was falsely accused of stealing a halter top from Albatross & Finch .
Girlie Boys
Cried after realizing she was putting on weight at Chocoholics' Anonymous.
Snow Job
Cried after Steph accused her of being a stalker and told her to leave him alone.
Later in the episode, she cried when Coach Halder mentioned penguin suits, which reminded her of a humiliating incident involving her and Steph.
Sweet 6teen
Cried because Tricia sabotaged her birthday party.
The One with the Cold Sore
Cried when she found out that there was a cold sore on her lips.
6 Teens and A Baby
Cried because she was covered in Emma's barf.
Blast From The Past
Cried because her boyfriend Spencer dumped her.
Great Expectations
Cried because she thought that Wyatt hated kissing her.
Bye Bye Nikki? Part 1
Cried because Nikki was leaving.
Bye Bye Nikki? Part 2
Cried because Nikki was leaving and because Nikki gave her an incredibly thoughtful goodbye gift.
Vote, Dude!
She mentioned that she forgot to feed her cat for a month, and after realizing it died, she started crying.
Episode
Reason why she cries
Breaking Up with the Boss' Son
Faked crying into thinking Corey cheating on her.
The Wedding Destroyers
Cried many times for several reasons:
The stress of the wedding.
Having to deal with her new brothers .
Accidentally flashing the Garcia boys.
The New Jonesy
Screamed, and cried into submission after she thought she kissed Smithy, but ended up kissing Jonesy.
Over Exposed
Cried twice when she felt humiliated over accidentally flashing Jonesy.
The Journal
Cried when her friends publicly embarrassed her by inadvertently reading her journal to the entire mall.
Whoa, Baby
Cried when she found out that her mom was having a baby.
Great Expectations
Cried after Travis Gibson broke up with her.
Cried when Jade broke up with Jonesy, which reminded her of her recent breakup.
Bye Bye Nikki? Part 2
Cried because Nikki was leaving.
Cried because of how heartfelt Nikki's gift to her was.
Episode
Reason why he cries
Mr. Nice Guy
Faked crying while in drag in order to elicit a compliment from Jonesy as part of Jonesy's training to be a nicer guy.
Fish and Make Up
Cried because Fish died.
Bye Bye Nikki? Part 1
Used a tissue to blow his nose because Nikki was moving away.
Episode
Reason why he cries
Mr. and Mr. Perfect
During a guitar lesson with Wyatt, he had a flashback about how he was tortured and started crying as Wyatt ordered him to play the "A" chord.
Bye Bye Nikki? Part 2
Cried after Jude pled with him for a chance to say goodbye to Nikki.
Episode
Reason why he cries
The Journal
Because he insulted as "self-absorbed lunkhead" from Jen's secret due to her friends reading it.
Episode
Reason why they cry
Over Exposed
Cried when Chrissy announced she was quitting the Khaki Barn in order to work at the Soft Rock Café . Cried when Nikki got an emergency call from Jen to meet in the food court.
Episode
Reason why he cries
The List
Cried after Jonesy threw the titular list into the mall's fountain.
Episode
Reason why she cries
The Khaki Girl
Cried because Caitlin got crowned the Khaki Girl after Tricia threw up all over the photographer.
Spring Fling
Cried (possibly fake tears) after Jonesy broke up with her.
Episode
Reason why she cries
Snow Job
Cried because she dumped Darth Mall right before the big dance.
Episode
Reason why she cries
Midnight Madness
Cried because Chad was leaving her dateless on New Year's Eve.
Episode
Reason why he cries
Bring It On
Is on the edge of tears when she drops Stanley off at Stick It the first time, and comes close to admitting that she needs to cry.
Episode
Reason why he cries
Various
Is seen crying when his mother drags him through the mall.
Episode
Reason why she cries
6 Teens and A Baby
Cried continuously throughout the episode.
Other Characters
Trivia:
Out of all the instances of the main characters, Caitlin Cooke had the most occurrences crying.
Wyatt is the inverse of them all because he had the least occurrences crying, and the shortest length.