The Return of Hydro-Man: Part 1 - S5-E7
Stupidity: When Spider-Man is working in the lab, he uses his webbing to barricade the door shut so no-one interrupts him. When Debra Whitman shows up and asks who is in there, he identifies himself as Peter Parker. When he is finished with his work, he leaves out of the window so that by the time the security guards break the door down, he has vanished. Since he used his webbing to keep the door closed, it would be pretty easy for Debra and the security guards to figure out that Peter is Spider-Man since Spider-Man's webbing is at the scene and Peter seemingly vanished into thin air.
Six Forgotten Warriors Chapter 4: The Six Fight Again - S5-E5
Stupidity: When the Kingpin has acquired all six keys required to access the doomsday device, he gives every member of the Insidous Six a key and promises them a share in the spoils, despite knowing that one of them is a traitor. He even acts dumbfounded when the Chameleon reveals himself to be the traitor moments later.
Chosen answer: Felicia and Peter's friendship in this series was depicted as being on-again-off-again. At this point in the series they may have been on good terms. Plus Felicia is a wealthy socialite and Peter and Mary Jane's wedding was a big event due to Wilson Fisk paying for all of it.
Phaneron ★