"Kiss and Tell"
- Alternate Aesop Interpretation: The intended Aesop of the episode is that you should wait until you are older to do certain things such as kissing, but it can also be read as "if you want something from someone, ask them for it directly instead of Hint Dropping." James only realizes that D.W. wants a kiss from him when she outright tells him that she does.
- Alternate Character Interpretation: Did D.W. only want a kiss from James so she could live the fairy tale Emily told her, that a kiss from a boy would turn her into a princess, and James was the best choice to fulfill it because he chose her song to be played at naptime? Or does she legitimately have a crush on him?
- Broken Base: Depending on who you ask, the scene where James kisses D.W. is either a Heartwarming Moment, or Squicky because the characters are only about four years old.
- Hilarious in Hindsight:
- Two years before this episode aired, the album "Arthur's Really Rockin' Music Mix" included a cover of "Brass in Pocket" by Pretenders, a song which tells of the female singer's attempt to get romantic attention from a man, sung in-character as D.W. This episode's premise is D.W. trying to get a kiss from a boy.
- D.W. being turned into a frog (in a fantasy sequence) after kissing James is funnier considering the plot of The Princess and the Frog, which came out six years after this episode's airing and also involves the protagonist turning into a frog from kissing someone.
- Squick: For some, the entire premise of the episode: a four-year-old seeking a kiss from a boy in a romantic context, and eventually succeeding.
- Toy Ship: This episode is where the "Jadora" ship originated, in fact.
