When Chris is asked out to a Knicks game, he must find a babysitter without his ex-wife Shelia finding out. Elsewhere, Gary and Marny find an unusual spot for some alone time. Meanwhile, Nick is in the dog house when he forgets about an important event with his wife, Emily.
Chris invites everyone over for a BBQ to meet his new girlfriend. When Nick learns of Chris' girlfriend's identity, he confesses they share a past. Meanwhile, Gary realizes trouble is headed his way because he forgot his wedding anniversary.
Marny has always wanted a girl and insists on giving it a try but Gary isn't too keen on the idea. Sheila organizes a child CPR class and signs everyone up. Nick and Emily reluctantly attend the class in hopes of proving they are good parents.
Gary's inability to effectively communicate with his son leads to unconventional disciplinary measures. Elsewhere, when Chris faces difficulty getting his son sleep trained, Marny imposes her services. Meanwhile, a school project brings out some unhealthy competition in Nick.
Marny agrees to take care of all four kids for the first time while giving Gary the day off. Elsewhere, the guys agree to help Sheila move out in hopes of retrieving Chris' Giants tickets. Meanwhile, a medical emergency might put Gary's rare day off in jeopardy.
When the President of their co-op board Miss Crane passes away, domineering resident Lydia Allendinger takes her place, much to the guy's chagrin. Utilizing her new found power, Lydia forbids Nick's annual Halloween hallway decorations, which leads Nick to take some drastic measures. Elsewhere, Gary and Marny desperately want to buy Miss Crane's old apartment to expand their living space and conspire to scare off any potential buyers.
Gary enlists Emily's help after complaining to Marny about their messy apartment. Chris and Nick have a situation on their hands when Freddie and Ernie lock themselves in the bathroom. Meanwhile, the guys confront Nick about always being unprepared.
Chris decides to throw Ernie's first birthday, but instead of sticking to a more traditional theme decides to take the party in a different direction. Elsewhere, Garyand Marny decide to get back in shape and begin a strict kale-only diet, which quickly proves challenging. Meanwhile, Sheila copes with the breakup of her relationship.
After a failed attempt to figure out who should spend Thanksgiving with their son, Chris and Sheila decide to spend the holiday together with his friends. Sheila plans a very traditional dinner in hopes of befriending the group. Elsewhere, Gary chooses to spend the holiday waiting in line to buy a brand new television during the Black Friday sales.
Gary and Marny try to spice up their relationship with help from Nick and Emily. Meanwhile, Chris and Sheila can't agree on who should keep their engagement ring.
Chris and Nick argue about who is to blame for Sheila's introduction into their lives. Gary discusses his life before becoming a stay-at-home dad and the origin of his chipped tooth. Meanwhile, Chris and Sheila patiently await the arrival of Ernie's first word.
When Gary learns of his father-in-law's disdain for him, he is willing to do whatever it takes to earn his respect. Elsewhere, with Chris' love life in a rut, he goes on a date with Shelia, prompting a horrified Nick and Emily to try their hand at matchmaking. Unfortunately their good will quickly turns into a competition at Chris' expense.
When Marny begins to feel overwhelmed with the pressures of her job and family, she is forced to lie to Gary in an attempt to find a few moments of solitude. Meanwhile, Chris signs the group up for trivia night. Unfortunately Nick and Sheila's highly competitive nature puts them at odds with the rest of the team.
After a near death experience, Gary and Marny worry about who will take care of their kids if they die. When Emily hastily agrees to be a guardian for the four kids, Nick tries to get out of it by making Emily look like a bad parent. Meanwhile, Chris becomes jealous of Ernie's new male nanny Andy.
Looking to re-enter the working world, Gary comes up with a new business idea much to Marny's dismay. With Chris' personal life in a slump, he decides to reinvent himself and take on an interesting new hobby. Elsewhere, Nick and Emily have a date night, but arrive home to find Chris in a very compromising situation.
With Gary's new career booming, he struggles to juggle both his career and responsibilities as a stay-at-home dad while trying to prove to Marny he can do it all. Meanwhile, Nick and Emily are eager to locate a missing toy that's sound is keeping them up at night. Elsewhere, Chris and Sheila are seriously concerned with Ernie's development after he is held back at his play group.
When Chris and Sheila contemplate having another baby together, Nick vows to do whatever it takes to keep them from getting back together. Later, Nick and Emily plan a divorce party to remind Chris of his horrible past with Sheila. Meanwhile, Marny's younger sister Bridget comes to town and is soon hired as Gary's assistant, much to his dismay.