Self-proclaimed, "prison matchmaker" Chelsea Holmes works with a shy young introvert, Brey, to connect him with two women on the inside. First, Brey has to convince his dad that this is a path worth pursuing. Things heat up for Isa and her inmate boyfriend Devin, but she still struggles to accept Devin's past. Meanwhile, Chelsea fears the worst when her boyfriend goes MIA in prison.
A heartbroken Chelsea moves on from inmate Manuel and onto inmate Michael, quickly forming an intense bond. A still somewhat reluctant Dexter gets his matches from Chelsea and is pleasantly surprised when he finds sparks with an inmate. Brey hits it off with Arlette but is taken aback when she reveals bits of her past. After dealing with Bryce's family drama, a triumphant Aluntra picks up Bryce from prison and the countdown to their long awaited wedding begins.
Things heat up between Chelsea and soon to be released inmate Michael when he asks her to pick him up at the prison gates and to officially be his gal. However, her excitement is short lived when he tells her that he wants to remain celibate while they get to know each other. Isa feels the full weight of dating an inmate as Devin asks her for money for commissary. Bryce is confronted by the fact that his incarceration left his family in shambles.
Chelsea picks up her boyfriend Michael from prison, and wonders if their relationship will survive with Michael on the outside. Dexter wants to visit Yolanda after she is released, but spots some red flags when she hints she'd like him to provide her with some high ticket items. Newly freed Bryce finds out that his family fell apart while he was away. As their wedding approaches, Aluntra worries Bryce will put their needs before hers. And Brey must make a tough decision after finding out Arlette has a violent past.
Michael’s flirty behavior on social media leaves Chelsea feeling “lightweight” anxious. Bryce blindsides Aluntra with his plan to help with wedding costs, but an explosive argument has her questioning their walk down the aisle.
Following a fight, Michael goes MIA so Chelsea flies out to Ohio to confront him face-to-face about the state of their relationship once and for all. Then, while prepping for their wedding, Aluntra and Bryce go to a dinner hosted by Bryce's family where they learn their true feelings about the impending marriage. After being stood up by Yolanda, a concerned Dexter enlists Chelsea to help him find out what happened. And, after a disastrous relationship with inmate Arlette, Brey shares some very surprising news with Dexter about his current love life.
