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Season Five (2014) Episode Number Date Aired
Revelations - Kailyn has a baby shower. Chelsea finds out Adam's had a baby with someone else. Jenelle has an abortion. Leah has a tough time coping with Ali's medical diagnosis. 1 January 21st 2014
Love Will Never Do Without You - Chelsea attends her first day back at school. Jenelle meets a new guy called Nathan. Kailyn and Jo argue over her move to Delaware with Javi. Leah takes a break and goes on vacation. 2 January 28th 2014
Keep Your Head Up - Kailyn and Jo have a verbal altercation when she drops off Isaac for a visit. Leah learns that Ali will need a wheelchair. Jenelle and Nathan move in together. 3 February 4th 2014
Working Overtime - Chelsea allows Adam to pick Aubree up from pre-school. Kailyn and Javi go house hunting and put in an offer.  4 February 11th 2014
You Got Me - Corey has a difficult time coping with the news about Ali needing a wheelchair. Jenelle and Nathan discuss having a child. Kailyn starts planning her wedding. 5 February 18th 2014
False Positives - Chelsea throws Aubree a birthday party. Jeremy is taken home after collapsing at work. Kailyn and Jo attend court again. Jenelle thinks she's pregnant. 6 February 25th 2014
These Are the Days - Jenelle receives news that a plea bargain could save her from a jail sentence. Chelsea lets Aubree meet Adam's new baby. Leah, Jeremy and Corey discuss how to handle Ali attending school. 7 March 4th 2014
Breakdown - Jenelle faces a surprise pregnancy. Chelsea has a visition request from Adam. 8 March 11th 2014
Miss You Much - Kailyn discovers her mother will not be attending her wedding. Jenelle continues to argue with Barbara. Chelsea takes Aubree to her first dance class. 9 March 18th 2014
We Belong Together - Leah is furious when Jeremy rejects a local job offer. Chelsea becomes an esthetician school graduate. Kailyn and Javi get married. Jenelle accepts her plea bargain. 10 March 25th 2014
Out of the Blue - Jenelle and Nathan have a check up on their baby. Javi drops Isaac off to see Jo. Adam replies to Chelsea's visitation objection. Leah has a hard time when Jeremy goes away to work whilst Ali receives her wheelchair. 11 April 1st 2014
What You See is Not What You Get - Leah and Jeremy take time to focus on themselves. Jenelle sees a doctor to discuss her pregnancy. Kailyn goes into labor. Chelsea has a difficult time agreeing on visiting times. 12 April 8th 2014
That's The Way Love Goes - Jenelle and Nathan's relationship issues continue. Leah learns what's caused Ali's illness. Javi returns to work causing Kailyn to stress about being home alone with two kids. Chelsea hears back from Adam regarding a visitation schedule. 13 April 13th 2014
Keep It Together - Kailyn's stress levels rise as she tries to maintain a happy family life and marriage. Leah and Jeremy are surprised when Ali voices her opinion on her muscular dystrophy. Jenelle and Nathan learn the gender of their baby. 14 July 16th 2014
When Everything Seems Wrong - Leah has difficulty working whilst being a mother. Nathan must turn himself into the police causing Jenelle to panic about the future. Kailyn invites Jo and his girlfriend, Vee to Isaac's birthday party. 15 July 23rd 2014
Overload - Nathan prepares to go to jail. Chelsea meets her lawyer. Leah begins taking medication to cope with anxiety. Kailyn and Javi visit Jo and Vee's apartment.  16 July 30th 2014
Harder Than It Looks - Chelsea investigates Adam's legal charges from his car accident. Kailyn celebrates her birthday. Jenelle struggles on her own whilst Nathan's away. Leah and Jeremy clash over finances. 17 August 6th 2014
I'll Be Missing You - Jenelle and Nathan reunite. Chelsea hears back from her new job. Leah and Jeremy visit Ali's specialist. Kailyn struggles with loneliness. 18 August 13th 2014
Family Matters 19 August 20th 2014
Bad Behavior 20 August 27th 2014
Cabin Fever 21 September 3rd 2014
Summer Daze, Summertime Sadness 22 September 10th 2014
Co-Parenthood 23 September 17th 2014
Wish You Were Here  24 September 24th 2014
All Grown Up 25 October 1st 2014

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