Greg and Jarvis try to convince Omar to finally patch things up with Keith; sparks fly when Keith runs into Jackee at a record store while Jarvis reconnects with his old assistant Danni during a protest against his arrest.
Keith bravely challenges Omar to a boxing match to salvage his manhood while Jarvis and Greg are caught in the middle. Jarvis comes up with a plan to finally win back his money at Eugene's next poker tournament.
Omar and Naomi are called to Caleb's school to meet with his Principal. Keith is frustrated with his new gig, photographing local rapper Lil' Day Day. Eugene plays matchmaker and gives relationship advice on his radio show.
Greg lands a job at a middle school and has an instant connection with Principal Wanda; Keith and Jackee get to know each other over an afternoon picnic; Kevin doesn't get a warm welcome when Jarvis introduces him to Eugene at his Cigar Lounge.
Omar and Naomi have an intense discussion about organized religion. Keith is nervous when he has to meet Lil' Day Day at a sketchy music studio to collect payment. Greg and Wanda have a rendezvous at a local bar outside of work. Jarvis and Lisa's conflict comes to a breaking point.
Omar and Eugene take Caleb on a guys trip to the great outdoors which proves to be too much for Eugene to handle. Keith takes beautiful photographs of Jackee for her birthday. Greg and Wanda begin to mix business with pleasure while Jarvis pays Danni a secret visit at a motel.
Keith doesn't approve of his Mom beginning to date again. Greg embarrasses Wanda at Omar's housewarming party. Jarvis finally finds out the person responsible for harassing him and Danni.
Things don't go as planned when Keith takes Jackee on a date for her birthday. Omar gets some unexpected news from a past acquaintance and Jarvis confronts Kevin about his true ulterior motives.
Omar, Greg, Keith and Jarvis reminisce about their childhood and give Omar advice on his marriage troubles.
Omar finally attends church and gives a powerful testimony that shocks everyone. Keith vulnerably professes his feelings for Jackee through poetry. Jarvis learns some truths that changes everything he thought he knew about his family history.
Omar learns some shocking information about Bianca; Greg gets out-hustled by an unwanted house guest; Keith notices his neighborhood is changing and blames his local councilman; Jarvis visits the man who claims to be his father.
Omar, Greg, Keith and Jarvis attend the Annual Quintessential Gentleman's mixer; Keith ruins the vibe when he confronts his local councilman over his rising rent.
Omar witnesses Naomi out with another man; Greg sets a bad first impression when he meets with Chef Williams; Keith meets Jackee's parents for the first time.
Greg makes himself a little too comfortable during date night at Jarvis' house; Jarvis confronts his parents about his past; Omar's late-night meeting with Bianca comes to an unexpected end.