Will decides to audition for his dream job as an on-camera weatherman; after Angie discovers that Graham has the word "farts" written on his forehead in permanent marker, she goes on a mission to obtain an apology from the responsible parties.
When Will's ex shows up unexpectedly for Sophie's birthday, Will gets frustrated that she undermines his rules; Miggy and Graham decide to give some items to charity but regret it immediately and seek out help from Douglas to get the items back.
Will wants to get back together with Mia, but must choose which family he wants to pursue; Angie kicks Will off the babysitting grid and fills the spot with Dr. Mark, Douglas' rival dermatologist; Graham is nervous about competing in a talent show.
Douglas agrees to baby-sit the kids on Valentine's Day; Douglas and Big Red band together to help Graham with his Valentine's Day emergency; Will and Miggy help Angie finish her deliveries so she can be with Owen on Valentine's Day.
When Poppy's ex-husband gets serious with his latest girlfriend, Poppy has to deal with the reality of another woman helping to raise her kid; Miggy gets cold feet after asking Douglas to remove his tattoo of Zara's initials.
Seeing that baby Jack is about to walk for the first time, Miggy tries to recapture his youth by throwing an epic party; when the party doesn't go as expected, he insists that Poppy and Douglas help him; Angie's boyfriend meets Graham.
In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie; Will saves one of the kids at school from a playground injury; Douglas insists Will capitalize on the glow from this heroic act.
When no one bids on "Lunch with KZOP's Will Cooper" at the school auction, Poppy and Sophie scheme to recruit Dr. Biscuits to bid on Will and play the role of his biggest fan; Douglas attempts to teach Angie how to cut back on extra spending.
To celebrate Angie's 30th birthday, Will throws a big party re-creating Ozzfest; Douglas takes Graham shopping to help him find the perfect gift for Angie.
Will starts to date someone new and ditches his TV-watching plans with Angie; Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.
Will forgets to send in Sophie's deposit for space camp, so he must woo the owner of the company in order to get her spot at camp back; Poppy deals with unwanted old feelings for her ex Ron as she helps him plan his wedding.
After learning that Angie's ex lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant; Poppy internally struggles with who she truly has romantic feelings for.
The kids are away for the summer, and the gang looks forward to their freedom; Angie obsesses over writing the world's longest email to her ex; Douglas inexplicably ghosts Poppy on their first date.
Will feels like everything is changing as Sophie returns home from camp a seemingly different person; Miggy gets a new temp job at Angie's law firm to help him earn more money to go toward Jack's preschool costs.
Angie goes into a tailspin when her long-absent ex-boyfriend Derek suddenly appears on her doorstep; Angie asks Will and Miggy for help because, despite his faults, she can't resist Derek; Douglas and Poppy try for a romantic second date.
Will is excited to become the coach of Sophie's soccer team; Douglas and Angie attempt to navigate what their friendship looks like now that they are roommates for the foreseeable future.
The kids head to the school for a spooky Halloween celebration with Douglas; Will has a stressful night trying to do too much; Poppy and Angie throw a Halloween party at Douglas' house to try to prove to themselves that they are cool moms.
Angie's one night stand turns out to be connected to the group in an unexpected way; Douglas confronts some family issues with a little help from Poppy; Will attempts to teach Miggy how to work on his disciplining skills as a parent.
Will gets busy cooking Thanksgiving dinner at Douglas' home; Miggy shows up to Thanksgiving dinner with the kids' teacher, Ms. Pronstroller, as his date, and he enlists Douglas' assistance in helping them form a connection.
When Graham brings Douglas' box of 1950s Playboy magazines for show-and-tell, Angie knows she has to give "the talk" to Graham; Poppy tries to become closer with the twins by helping them discover their individual personalities.
When Graham writes a letter to Santa asking for either a white Christmas or to meet his father, Angie goes on a mission to find snow; Rory, Emma and Amy find out that Poppy and Douglas are romantically involved.