Darlene is in for one surprise after another when David introduces his girlfriend, Blue, at a parent-teacher conference and mentions that Mark and Harris will be spending the weekend with them. Dan hires Becky to help out at work, but they both come to learn that she might need more help than she can offer.
It’s Halloween, the favorite time of year for the Conners, but an email from the school banning certain costumes, including Mark’s, sets off an argument between Dan and Darlene. Jackie introduces someone new to the family at the Halloween party and insists that Dan vet him, only to immediately wish that she hadn’t.
With Mark and Mary’s help, Jackie convinces Dan to build a chicken coop in the backyard so the family can eat organic eggs, but from a bird’s-eye view, it appears that she may have ulterior motives. Becky meets with Andrea for the first time since the surrogacy mishap, and Darlene is forced to deal with a sleazy customer at her casino job.
As Darlene grapples with a life-changing offer from Ben, an unexpected conversation with David turns her world even more upside down. Relationship problems lead Jackie to the bottom of the bottle at the last place she remembers being truly happy. Becky’s hopes of a happily ever after with Emilio are jeopardized when Dan delivers alarming news.
In the wake of Emilio’s deportation, Jackie steps into the role of a paternal figure and creates a meticulous birth plan for Becky; but as the Conners know, nothing ever goes according to plan. Meanwhile, Darlene is tangled in a complex love triangle with David and Ben, and – like her mother – Harris is caught up in a problem of her own.
Becky thinks that Jackie’s new friend Dawn, a restaurant supplier, is only cozying up to her to sell them things they can’t afford for the Lunch Box. Darlene is thrilled when Harris gets into Central Illinois State, but Harris might have found a better offer on her own. When Dan finds himself in an embarrassing situation nursing an injury, Louise tries to help him out.
Dan starts to bond with his younger half-brother but he can’t get over the fact that their father paid for Ed Jr.’s college education, something he refused to do for Dan. Jackie hits it off with a fun married couple, so much so that they “invite” her into their relationship. Harris and Mark do not react well to the news that Darlene is trying to have a baby with Ben.
Harris is the boss of Darlene after her mom, desperate for money, gets a job at Price Warehouse. Jackie decides to take her “thrupple” relationship with Ron and Janelle to the next level. Everyone makes fun of Ben’s appearance after he shaves his beard in an attempt to appear more clean-cut to potential advertisers for the magazine.
Bev is back from Arizona and has come to the realization that she’d like to use her finances to spread happiness. She has decided to fund Mark’s tuition to a prestigious coding camp, while Darlene tries to convince her to give the money to Harris instead. Dan realizes how much he misses Louise, and Becky persuades him to visit her on tour
Dan and Louise take their relationship to the next level and come to appreciate the complexities of aging. Meanwhile, Darlene spends the night in jail and hands off parenting duties to Ben. Mark and a friend work on a class experiment that leaves them both with hickeys, and Becky contemplates marrying Emilio.
Darlene and Ben go apartment hunting as they take on the next step in building their life together. Jackie and Becky take Beverly Rose on a road trip to Mexico to meet her father for the first time while Dan reluctantly shares his financial troubles with Louise as he struggles with the pending foreclosure of the house.