PlotJessie introduces the children to Miami Heat player Chris Bosh who is going to be playing the New York Knicks. In order for the Knicks to win, Luke washes out the luck of Chris' socks so he loses. Later on, Chris starts to lose his skills in basketball to Luke's dismay. Meanwhile, a famous fashion designer sends Emma a dress to review on her fashion blog; however, things go awry when Jessie accidentally damages the dress.
- Debby Ryan as Jessie Prescott
- Peyton List as Emma Ross
- Cameron Boyce as Luke Ross
- Karan Brar as Ravi Ross
- Skai Jackson as Zuri Ross
- Kevin Chamberlin as Bertram Winkle
- Chris Bosh as Chris Bosh (Himself Technically)
Jessie: Well I meant Toosh but it's hard to find words that rhyme with "Bosh".Luke: How about "Squash"?
Zuri: "Slosh"?Jessie: I was nine.
- The title references the reality show Say Yes to the Dress.
- Arturo Vitali from The Suite Life On Deck was mentioned in this episode.
- This episode aired on Karan Brar's 14th birthday (January 18,1999).
- Unlike other "It's a Laugh Productions" series, when the camera zooms to Chris Bosh for the first time, a cheer crowd is not heard even though he is a celebrity in real life.
- There are multiple references made to LeBron James.
- Because of the Tipton Tea billboard (Tempest in a Teacup) and the mentioning of Arturo Vitali, it is most likely that one of the characters from The Suite Life 'On Deck may appear on the show.
- Jessie says she met Chris Bosh back when she lived in Texas which in reality is actually where he was born.
- In the scene where Zuri is unzipping the dress, she is pulling on the back, when you can see that it is under Jessie's right arm.
- It is unknown why Jessie couldn't have just borrowed Christina's dress because she would have approved.
- Jessie explained to Chris that he had cheered at her high school. She then says she didn't know what rhymed with "bosh" because she was nine at the time. But a nine year old does not go to high school. Most likely she was in the audience and she was referring to the high school she went to years later.
| To view the Say Yes to the Messy Dress gallery, click here.