"Purr-fect Partners" really did it when Dudley has entered Snaptrap's lair to retrieve the chew toy that he's been trying to chase after. In the process, he takes down the bad guys, only leaving Snaptrap, who has grabbed the toy, behind. You'd Expect: Since that he has taken his toy, Dudley will take him down for that and then he gets it back. Instead: He only grabs it and laughs maniacally with Snaptrap for a few seconds before he escapes in the escape pod.
The matter of the Chief taking in Dudley as a TUFF agent. You'd Expect: For Keswick (who is the smart one) to point out that putting an idiotic dog with an only sane cat together on the same page is a bad idea, not after his idiocy has led her getting injured and letting Snaptrap get away. Instead: The partnership is put together and it's a train wreck. Eventually, they got better when their teamwork defeat Snaptrap.
In episode "Doom-Mates" where Kitty kicks Dudley out of her apartment through a slide to her giant litterbox after getting fed up with his ways of protecting her from the Chameleon. Suddenly, a knock on the door came and it's Dudley. You'd Expect: Kitty should take a hint that it's the Chameleon in disguise since Dudley is still on the slide down to her litterbox. Instead: Via Puppy Eyes, she lets him in, and what do you know, it's the Chameleon in disguise on her door and getting his chance to kidnap her through this.
"Mall Rat" has Snaptrap being released from jail and is claimed to be redeemed. Only Kitty remains unconvinced by this. You'd Expect: Until she gets proof of her claim, she has to play along with his attempts of giving out his goodies to everyone in Petropolis. Instead: She started ruining everything that he has given out to them; muffins, sunshine, thinking it's his evil devices. As a result, everyone in Petropolis started to hate her for it, even the agents in TUFF. Luckily: As soon as everyone (including her) is trapped in Snaptrap's mall, it turns out Kitty's right; he's not redeemed after all.
"Share-a-Lair" would have one when T.U.F.F. and D.O.O.M. are launching missiles on each other's hideout due to a field agent in their organizations stating that one is declaring war on the other when in fact they're weren't. You'd Expect: Each of the organization will have a spy to keep a close eye on the field agent if he's trying to make false alarms or so. Instead: They don't and started to blow up each other's hideouts until they are forced to share an apartment room. Even Worse: Their idiocy ended up being a plot orchestrated by the Chameleon, wanting revenge on T.U.F.F. for putting him in prison and D.O.O.M. for not inviting him on a social event together.
In "The Wrong Stuff", Kitty is going out with her former partner, Jack Rabbit. The problem is, Dudley doesn't trust him so he attempts to follow them, but is caught every time. Finally had enough of this, she decided to join his new organization, S.T.U.F.F. While being seated on a chair, Jack admitted of how he drains information of super agents' brains and sell it to super villains. You'd Expect: She would take a hint of this, concludes her business with him, and leave S.T.U.F.F. so that she could warn Dudley about Jack. Instead: She thinks what Jack said is a joke. That is until he cuffs her to the chair that is, so cue My God, What Have I Done? moment when she finally realize Dudley's right about distrusting Jack.
"Frisky Business" has Dudley's mother Peg leaving him in charge for 3 days by himself. Next thing is that Dudley would do some things she forbids him to do. You'd Expect: Someone from the neighborhood should call a babysitter for him or a social service to verify if he could take care of himself. Instead: Nobody does on the above. As a result, Dudley ended up being a wreck like sleeping during the job, not wearing proper clothing, and putting the house on a big mess.
In "Doom and Gloom", Larry points out to Snaptrap the reason his plans keep on getting foiled is because he kept on revealing them to the T.U.F.F. agents. You'd Expect: That Snaptrap to realize that Larry may have a point in all this and considers in taking his advice. Instead: He sends him to the shark tank for the remark, resulting in him quitting after he can't his abuse anymore. You'd Expect: Both Ollie and Francisco to call him out for this. Instead: They just run off with Larry just to avoid in taking turns being thrown to the shark tank. As a result, Larry becomes a more dangerous villain without telling anybody of his evil plans. Whoops.
"Diary of a Mad Cat" has lot of these moments.
Dudley and Kitty are in a contest called, "Do You Know Your Partner?" and the host questions the former of what is the latter's species. You'd Expect: "Cat" is his answer. Instead: "Squirrel" is what he said which it's wrong. As a result, only the Chief and Snaptrap with their partners Keswick and Larry are going on a trip to Maui, leaving Dudley and Kitty behind. To make it more knowing, the host asks Dudley if he even knows where Kitty lives. So Now You'd Expect: He will remember that he did went to her home once in "Doom-Mates" and therefore, his answer should be that she lives in an apartment with a cat-themed rooftop. Instead: He answered she lives in a statue in the park like all other squirrels, much to Kitty's chagrin.
Kitty is disappointed Dudley doesn't know much about her when she knows much about him. When he retorts on that statement, she reveals how she knows about his favoritism of bacon and the places he visited that sounded like bacon. You'd Expect: He would take a hint that ever since he became a T.U.F.F. agent, she is getting to know him as soon as they're introduced, and should apologize for not thinking straight to her about it. Instead: Dudley callously thinks that Kitty only knows about him much is because she's spying on him from her squirrel-nest, pissing her off that she's going to write down nasty things about him in her e-diary. Ouch.
Guilty that he doesn't know much of Kitty, Dudley has decided to read her diary while she's away helping the Chief, Keswick, Snaptrap, and Larry pack their things up. While doing so, he ended up seeing a bug on the keyboard. You'd Expect: He should flick it off. That way, there will be no accidents in anything that will happen bad in her laptop. Instead: He presses on the keyboard with his hand to get it off. This action caused her diary to be e-mailed by everyone in Petropolis for the villains to read it and mock her for her weaknesses. Way to go, Dudley.
In a fight against Bird Brain, he revealed that Kitty has a secret crush on water delivery guy, Eric. This eventually puts her down. You'd Expect: Dudley to remove the mind control helmet on him. Therefore, this problem should be solved easily. Instead: He plans on punching his face, prompting Kitty to stop him from doing so, which resulted in letting Bird Brain get away with this.
Next, Dudley and Kitty have a call from Keswick that the Chameleon is causing trouble. As they arrive, he started to shapeshift as her mother. You'd Expect: Upon seeing him shapeshifting, Kitty should take a hint about it and just blast the Chameleon. Instead: She hesitated, giving him the chance to tell her off from what she wrote about her mother in her diary. As a result, she lost her confidence to fight and runs away from the fight.
Regaining her confidence to fight after a talk with Dudley, Kitty planned on reading the villains' diaries to see their weaknesses. Then they confront the Chameleon and Birdbrain about it. You'd Expect: They would realize that they were now in either way with their weaknesses known to the two so they just make a run for it before either Dudley or Kitty could take them down from what they learned about them. Instead: They gloat that they don't have a weakness at all. Therefore, Kitty ended up showing a mirror with a bell on Biradbrain and a sadistic gym coach for the Chameleon, taking them down once and for all.
Even Dudley is no better in Sequel Episode of "The Wrong Stuff", "Freaky Spy-Day", when he switches brains with Kitty to keep an eye on Jack. His excuse for wanting to go T.U.F.F. headquarters? He left his sunglasses in the top-secret computer room. You'd Expect: Dudley shouldn't believe of his excuse and continue to suspect him. Instead: Being an idiot, he falls for his excuse and before you know it, Jack is using that excuse to steal the T.U.F.F. agents list and sell it to Snaptrap. Kinda ironic, don't you agree?
When Quacky has turned villain since his second episode appearance, he makes appearances as a villain afterwards and asks Dudley and Kitty to be part of his plans. You'd Expect: They would remember of his action when he tried to blast them to outer space so they shouldn't give him shit. Instead: They fall for it. Every single of his appearances after his second one.