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- Season 5 overviewAug 31, 2015-May 24, 201624 episodesSeason 5 episodes1. Prank Amateurs Aug 31, 2015
- Jenna hears a disturbing secret that threatens her resolution to stop thinking about Matty.
- 2. Short Circuit Party Sep 7, 2015
- Jenna causes an accident at school with surprising results; Matty deals with the fallout.
- 3. Jenna in Wonderland Sep 14, 2015
- Jenna gets a taste of popularity while Matty struggles with being shunned.
- 4. Now You See Me, Now I Don't Sep 21, 2015
- The senior yearbooks are released; Jenna is depressed when she sees her superlative.
- 5. The Dis-Engagement Dinner Sep 28, 2015
- Jenna is forced to throw Tamara a party for her fake engagement; Gabby reveals a secret about Matty.
- 6. Don't Dream It's Over Oct 5, 2015
- Tamara accuses Jenna of sabotaging relationships, so Jenna confronts her ex-boyfriends.
- 7. The Big Reveal Oct 12, 2015
- Jenna wants to tell Matty the truth.
- 8. An Indecent Promposal Oct 19, 2015
- Prom season arrives at Palos Hills High School; Jenna receives some surprising news.
- 9. Say No to the Dress Oct 26, 2015
- Jenna refuses to let a series of obstacles ruin her chance at having a dream prom.
- 10. Reality Does Not Bite Nov 2, 2015
- The prom takes unexpected turns.
- 11. The Graduates Nov 9, 2015
- When Sadie Saxton is forbidden from walking at graduation, plans go awry.
- 12. Holding on and Letting Go Nov 9, 2015
- Everyone tries to make the last night of high school count.
- Jenna's newfound confidence is shaken when she discovers she is not the only one who has changed.
- 14. Wtf Happened Last Year? Mar 22, 2016
- Jenna reveals what happened in the last year, including the freeze between her and Matty.
- 15. The Friend Connection Mar 29, 2016
- Jenna refrains from a new relationship; Tamara throws a chic birthday party for Sadie.
- 16. Best Friends For Never Apr 5, 2016
- Jenna hooks Tamara up with an internship but finds that working with friends can be a disaster.
- 17. Fireworks Apr 12, 2016
- Jake secures shifts for Jenna and Tamara at the country club; Sully's plans for a party.
- 18. Digging Deep Apr 19, 2016
- Jenna and Matty continue to rekindle their friendship while they throw a party for Jake.
- 19. Girls Gone Viral Apr 26, 2016
- Jenna must decide between success at Idea Bin and her friendship with Matty; Jake hooks up.
- 20. Misadventures In Babysitting May 3, 2016
- When Jenna volunteers to baby-sit, Matty helps; Tamara and Sadie are in over their heads.
- 21. Living in Sin May 10, 2016
- Jenna takes things with Luke to the next level; Tamara's debt comes back to bite her.
- 22. Home Again, Home Again May 17, 2016
- A fight with Luke pushes Jenna to sign up for her camp reunion and towards reconnecting with Matty.
- 23. Second Chances May 24, 2016
- Help from Luke lands Jenna an important meeting at SCU; Tamara comes clean to Patrick.
- 24. Happy Campers, Happier Trails May 24, 2016
- Help from Luke lands Jenna an important meeting at SCU; Tamara comes clean to Patrick.