The Dis-Engagement Dinner
Season 5, Episode 5
Air date September 28, 2015
Written by Shawn Simmons
Directed by Ashley Rickards
Episode Guide
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The Dis-Engagement Dinner is the fifth episode of the fifth season, and it aired on September 28, 2015. This episode marks the second episode of Awkward directed by Ashley Rickards, who plays Jenna Hamilton. 


Jenna's forced to throw Tamara a party to celebrate her fake engagement. Meanwhile, Gabby reveals a secret about Matty that send Jenna in search of the truth.


Cast and Characters

Main Cast

Recurring Cast

  • Erinn Westbrook as Gabby Richards
  • Niko Pepaj as Sergio
  • Cayden Boyd as Brian 
  • Brando Eaton as Adam Walker


  • Olive and the Dukes - “The One That I Gotta Have!”

(scene: Jenna and Tamara talk at Tamara’s party)

  • Rebecca Jade and the Cold Fact - “Further Again”

(scene: Jenna talks to Adam, Gabby and Brian at Tamara’s party)

  • Kid Sister - “Leave the Lights On”

(scene: Jake talks to Matty during Tamara’s party)

  • Iris - “I’ll Wait for You”

(scene: Jenna talks to Matty to try to find out what Gabby was talking about)

  • Kid Sister - “Heartbreaker”

(scene: Brian talks to Jenna about being unsupportive of Adam and Tamara)

  • HAERTS - “Heart”

(scene: Jenna makes up with Tamara for what she said at the party)

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