"I'm never gonna..."
- Pam when she's engaged to Roy. You can't help but feel awful for her when she's in that toxic relationship. And just after she calls off her engagement with Roy, she has to deal with the pain of watching Jim date Karen. She gets back with her ex-fiance out of loneliness, after he's spent all season trying to earn her back, but when she does, he's insensitive about her art-work, and furiously makes a scene when he discovers she kissed Jim. It's at this point Pam learns to gain courage and honesty, starting with cutting off Roy for good.
- Phyllis can be one whenever she's picked on by Michael.
- While he is normally a creepy idiotic pervert, one Cold Opening has Kevin going out of his way make chili for everyone in the office, proudly declaring that it's his greatest skill. As soon as he walks in the door (after carrying it up the stairs due to a broken elevator) he trips and spills it all over the carpet. Seeing the big guy trying in vain to scoop it all back into the pot just makes you want to give him a hug.
- Kevin also seemed pretty Woobie-ish in the episode where he and Andy protested to get their parking spots back, while at the same time Kevin deals with his fiancee breaking up with him. After they win the parking situation at the end, Kevin says with a warm smile, "It's just nice to win one."
- Kevin again, when he explicitly compares himself to an alternate future version of Jim that had never gotten together with Pam.
- And yet again, when Michael makes him eat the butt of a piece of broccoli.
- Andy has some Woobie elements too.
- Erin is an orphaned Pollyanna who just wants everyone to like her, but she seems to have been fleshed out into a full-fledged woobie as of "Secretary's Day". She had a cringe worthy Heroic BSoD when she found out that Andy and Angela used to be engaged: her breathing pattern became irregular, she pulled her hair to her face, and started yelling.
- Erin: In the foster home, my hair was my room.
- Turned up to eleven when Michael lands a devastating blow during an argument in "Viewing Party" (though in fairness, he picks up on the mistake uncharacteristically fast and immediately moves to fix it).Michael: I'm not your dad!
Erin: (cue massive teary doe eyes)
- Jim and Dwight had their moments. Jim during the lowest points of his pining for Pam; Dwight after Angela dumped him (especially when, after he defeated the computer in a sales competition and Angela didn't care, Pam, who had been impersonating the Dunder-Mifflin computer network as part of a prank, sent him an instant message admitting its defeat. Dwight cries).
- Young Michael on the videotape in "Take Your Daughter To Work Day" (which goes a long way towards explaining parts of his adult personality): "I want to get married and have a hundred kids, so I can have a hundred friends, and no one can say no to being my friend."
- When then turns into a painfully hilarious moment when the kids and crew are struck silent by this, complete with the Muppet Expy doing a subtle Jaw Drop.
- Young Michael wetting his pants at his mother's wedding definitely qualifies as well- as does most of his childhood to be frank.
- Michael is especially woobie-ish in "Stress Relief: Part 2", as the only Jerkass thing he does is giving everyone a well-deserved comeback speech. He finds out that he causes stress for everyone in the office, and, because he genuinely wants them to be at peace, hosts his own event for them to speak their mind. Instead of giving him opinions, however, they flat-out insult and mock him, and he ends up leaving in tears.
- Even Angela gets in on it at one point, when Dwight gives her the news of her cat Sprinkles having died (via Dwight euthanizing her no less!). Pet owners can relate.
- Jordan, every time she interacts with Dwight.
- Even Gabe occasionally slides into this territory. He's extremely awkward and uncomfortable to be around and can admittedly be an uptight jerkass at times, but it's hard not to feel bad for him sometimes. He regularly gets made fun of, insulted, and body-shamed, and even his own girlfriend tells him that she doesn't like touching him and hates the sound of his voice. Not to mention the scene where Erin breaks up with him on stage in front of everyone at the Dundies.
- Brian the sound guy has to simultaneously endure losing his job and getting divorced. Adding to that is the fact that he's fully aware his crush on Pam is one-sided and you really have to feel for him.
- Toby throughout the series whenever he's picked on by Michael and especially in the series finale. Almost everyone else has some kind of a happy ending except for him. Dwight fired him a year earlier and he tries to make it as a novelist in New York. He tries to re-connect with Nellie but she rebuffs him. At the forum for the documentary, an audience member asks them if they find their life feels pointless now that they're no longer being filmed and he automatically says yes. When crying while dancing with Pam at Dwight's wedding she asks is it her or Nellie, and Toby cries "It's everything." However, the series finale does end with a Hope Spot for him, as he seems to have a more positive outlook by the end of the wedding and accepts his former coworkers' invitation to go out drinking.
- Stanley, considering that he (understandably) is very unhappy with his job, mostly thanks to Michael constantly making him the butt of jokes, and even tells the audience in the episode "Stress Relief, Part I" that he can't quit since he's "too old" to find a new job and he doesn't have enough money saved up to retire. On top of that, in the same episode, he nearly dies of a heart attack, thanks to Dwight's appalling "fire drill" (which causes fear and panic in all the employees).
- Holly. Being a Distaff Counterpart to Michael who's notably not a Jerkass, when first introduced, it's immediately clear she's this. There's many points where she's humiliated or mistreated in front of others, either because of her poor mannerisms, a misguided prank, or being victim of someone else's Jerkassery. She says early on that she was bullied in middle school and implied that it continued after that, and her reaction to things, quietly standing still taking whatever embarrassment or mistreatment she's suffering, really do a good job conveying such.
- Helene Beesley (Pam's mother), whose husband decides to leave her, and later dates Michael, only to have her heart broken by him on her own birthday, simply because he thinks that she's "way too old" for him, even stating that he feels as though he's "robbing the grave" to her face! Poor Helene really didn't deserve any of that insensitivity from Michael!
