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.
The Conners are dealing with the pandemic, and life’s financial troubles loom over the family. Dan is still trying to catch up on back-mortgage payments and avoid a potential eviction, while the Lunch Box is closed for everything but takeout and delivery. Becky and Darlene are both forced to search for additional income at the newly reopened Wellman Plastics plant.
Darlene isolates herself from her co-workers at Wellman Plastics, leaving them with the impression she is an elitist snob, while Louise decides to teach Harris an expensive life lesson. Jackie has invested everything she has into The Lunch Box and is determined to keep the restaurant running no matter what, leaving some family members to question her actions.
Chuck’s new purchase of a boat creates a rift between Dan and his longtime friend. Meanwhile, Darlene hires her first assistant at Wellman Plastics but soon realizes she is anything but helpful, leading Darlene to question her decision. Elsewhere, Jackie is laser-focused on her dream of being a contestant on “JEOPARDY!” and believes the late, great Alex Trebek wants her to go all the way.
After Ben declines Darlene’s proposal, she starts to ponder why she tends to be so negative in life, prompting her to start a journey of self-discovery which leads to Pastor Phil. Meanwhile, newly appointed City Councilman Don Blansky puts Jackie in a tough position as she and Neville are ready to open the new and improved Lunch Box.
Part of Becky’s recovery program mandates she make amends with people she has lied to over the years, leading her to meet up again with former high school friend Mikey to apologize for lying to him about her living a successful life. Meanwhile, Darlene visits with Pastor Phil, and Louise continues planning her wedding.
The Conner home is decked out for Halloween despite the leak in the roof that forces Dan and Louise to cancel their honeymoon. But all is not lost when Becky surprises the newlyweds and takes them on a virtual adventure around the world. Meanwhile, Darlene continues her spiritual journey, and Harris introduces Aldo’s children to the family, where more tricks than treats await.
Darlene continues to navigate her breakup with Ben, and when she and Becky head to the movies and see Ben on a date, Darlene can’t stop herself from interfering and making everyone uncomfortable. Meanwhile, Dan offers to talk with Aldo’s dad, Jesse, when he doesn’t approve of Harris and Aldo’s relationship.
Darlene falls in love with a house she’s looking at, but when the realtor shares she has a better chance of getting the house if she’s part of a couple, she convinces Ben to pretend to be her partner. Meanwhile, Becky and Professor Davis are finding it hard to continue keeping their relationship a secret.
As Darlene struggles to cope with the stress of construction, a serious accident leads her to reevaluate everything and make a life-changing decision. Lou, a familiar face from the past, returns as Mark’s combative contrabassoon teacher, but after he butts heads with Mark, Dan steps in, only to realize that their similarities may outweigh their differences.
The Conners gear up for a megawedding! Jackie and Neville, Darlene and Ben, and Harris and Aldo are planning for a shared big day, but along the way they discover that some of the couples may not be on the same page about their happily ever afters. Meanwhile, Dan and the family have decked out the house for the occasion, but will all six of the lovebirds make it to “I do”?
In an effort to save money, newlyweds Darlene and Ben and Jackie and Neville head off on their joint honeymoon, where their cost-saving measures contribute to a tension-filled getaway. Elsewhere, Dan, Becky, Harris, Mark and Beverly Rose head off for a night at a waterpark, where Harris and Mark bond in an unexpected way as Mark copes with the news that his ex-boyfriend is dating someone else.