Season 5

When Phillip makes a shocking decision, Jeremy rethinks the way he handled the recent argument between them. Everybody is worried about Phillip's safety, and Jeremy wonders if his tough love did more harm than good. Mr. Brown goes through a breakup.

Leah wants to try for another baby; when Jeremy plays hard to get, Leah hatches a plan to seduce him; Mr. Brown has to babysit Kimberly's grandson who appears to be the perfect angel, until he reveals himself to be a mischievous handful.

When Efe's foundation offers free D.N.A. tests, Karen participates and discovers something; Leah employs Two Hunks and A Trunk to spur Jeremy into action to complete his "honey-do" list.

Vinny's nightmare makes him want to get saved; Mr. Brown does the baptizing, while Lindor is up to his neck in everyone's IT needs.

Jeremy and Leah hatch a plan to make Philip realize his worth and get out of his toxic relationship. Meanwhile, Anastasia lands a big audition that could help her get back on top.

Cora has been contacted by an old crush from high school who shows up, and to her surprise, he proposes; Leah gets concerned when Jeremy starts coming home later than usual and spending time with single friends she's never met.

Sandra has been ghosting Lindor because she moved on to a new college boy so Lindor uses the family to try and win Sandra back; Mr. Brown writes his first gospel rap hit Drippin' Jesus and immediately releases it.

Reginald shocks the Pleasant Days crew when he begins behaving in uncharacteristic ways; Efe knows why but struggles to keep Reginald's secret; Karen challenges Vinny to a cook-off.

Vinny's weed smoking is making him a bad role model for Philip, so he attempts to rehab his image by volunteering at Cora's church; Cora lands a date with a promising gentlemen.

Philip gets caught watching porn by Leah, Jeremy brushes it under the rug causing a major rift between he and Leah because of Jeremy's betrayal. Efe encourages a role reversal exercise that brings all of Jeremy and Leah's,thoughts to light.

Sandra wants to switch her college major, but she's afraid to tell her parents.

Sandra utilizes her social media skills to help Anastasia launch a PR campaign to rehab her image, but they find out Anastasia's longtime actress rival is fueling a smear campaign against her.

Jeremy and Leah can't seem to see eye to eye on how to spend their unexpected and welcomed I.R.S. refund check. Anastasia and Vinny have their hands full trying to help Theodore study for science.

Leah shocks Jeremy with some baby-making trends she wants to incorporate into their daily routine, but he finds them annoying and unnecessary; at the same time, Sandra and Philip take charge when a possible social media ban threatens their status quo.

When Jeremy sees a throwback photo of him and his best friend and college roommate, he reminisces about his college days and decides to track him down to reconnect after many years.

Anastasia needs to write and perform an original monologue but is running out of time and has to swallow her pride and get Mr. Brown's help, whom she just called an amateur.

Jeremy enters a charity boxing match, only to find out his opponent is Leah's wealthy ex. Mr. Brown hires someone huge and unexpected as his trainer. Meanwhile, Reginald is on a quest to regain his youth and solicits Philip to give him a new look.

Jeremy and Leah wonder if Leah has infertility issues, so they visit a doctor to get tested. But when the tests come back that both Leah and Jeremy have fertility issues, they have a decision to make.

Jeremy helps Vinny track down who stole his mouth-watering ribs, and Phillip acts tough to win over Chilecia's brother, a former gang member.

After suffering chest pains, Vinny is upset to learn he must be substance-free for 24 hours, and Phillip, after procrastinating too long, uses AI to write a school paper for him.

Anastasia gets an opportunity of a lifetime, but it comes at a cost she isn't sure she can afford. Meanwhile, Mr. Brown and Cora help Philip with his prom-posal to Chilecia.

Sandra goes helicopter parent on Philip when she notices he's playing with fire. The crew organizes to give Reginald the surprise of his life.

A shocking truth is revealed as Jeremy and Leah force Phillip and Sandra to come clean; Mr. Brown takes a deep dive into conspiracy theories.

Reginald must face a daunting truth with his son Brandon; Vinny starts a business venture that throws Pleasant Days into a chaotic spiral.

Jeremy and Leah are forced to put their foot down upon receiving disappointing news concerning Phillip.