Between the Swoon and New York City is the twenty-first episode, and also the first part of the 2-hour Season 3 special, and the 73th episode overall. It aired on September 19, 2014.


Jessie meets a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield’s son. Meanwhile, Ravi gets a rare baseball, so Luke tries to steal it, and Bertram has to take care of Zeus, the dog of Mrs. Chesterfield, who doesn't want Brooks dating Jessie. Zuri and Emma, seeing the two dating, want Jessie to date Tony instead.

TO BE CONTINUED In No Money, Mo' Problems


Main Cast

Guest Cast


  • This is the first appearance of Brooks.
  • Jessie starts dating Brooks in this episode.
  • The title of the episode is a reference to the song Arthur's Theme. The original line is "caught between the moon and New York City".
    • The title most likely refers to Brooks being the 'swoon', and Jessie's relationship with him and New York City.
  • The scene where Luke tries to steal Ravi's baseball and is almost crushed by a boulder falling down the stairs is a parody of Indiana Jones. The dramatic theme, the baseball on the pedestal and the boulder all refer to it.
  • It is revealed that each time she gets married, Mrs Chesterfield changes her last name.
  • It's revealed that Brooks is Mrs Chesterfield's son
  • This episode hints that Mrs Chesterfield's hairdresser and most of his husbands are dead


  • On the episode The Talented Mr. Kipling in Season 1 of this show, Mrs. Chesterfield says that she is only 32 years old. But, on this episode, she has a son that's slightly older than Jessie, and Jessie is almost 21 years old at this time. The question is: How old was Mrs. Chesterfield when she gave birth to Brooks?
  • Mrs. Chesterfield is actually Brook's new stepmother.


Jessie logo
To view the Between the Swoon and New York City gallery, click here.


Jessie-Between the Swoon and New York City Promo

Jessie-Between the Swoon and New York City Promo