Will è un padre single divorziato, sua moglie ha lasciato sia lui che la loro bambina Sophie, l'uomo cerca di coinvolgere gli altri genitori dell'asilo a prendere parte a più attività ricreative, ma gli altri genitori single non sono interessati, loro formano un gruppo: Angie, madre di Graham, Douglas, dermatologo attempato vedovo della moglie e padre delle piccole gemelle Emma e Amy, Poppy che è la madre di Rory, e infine Miggy, suo figlio Jack è solo un neonato ma dato che è un giovane ragazzo padre si è aggregato al gruppo per imparare a fare il genitore.

Dato che Sophie, Rory e Graham andranno a fare un pigiama party a casa di Emma e Amy, Will decide di cogliere l'occasione per aiutare Douglas dato che non ci sa fare molto con questo genere di cose, in realtà Will vorrebbe avere un amico e spera di trovarne uno proprio in Douglas sennonché i due non hanno praticamente nulla in comune.

Mentre i bambini giocano insieme Rory inavvertitamente uccide il porcellino d'India delle gemelle, ma le bambine sembrano indifferenti alla cosa. Angie non accetta che Graham abbia stretto un legame così forte con Will, infatti sembra che si senta più a suo agio con l'uomo di quanto lo sia con la sua mamma.

Miggy non ha idea di come far addormentare il piccolo Jack, su questo argomento Douglas si vanta di aver gestito bene la cosa insegnando alle gemelle, quando erano neonate, a dormire senza coccolarle, affermando che le donne al contrario non hanno abbastanza forza di carattere perché coccolano troppo i bambini.

È Halloween, e Will organizza una festa a casa sua alla quale prendono parte i suoi amici con i loro figli, Sophie invita un ragazzo, Carol, e questo mette in agitazione il padre, che comunque cerca di accettare la cosa.

Will si trova molto bene con la pediatra di Angie e Graham, ma Angie è preoccupata che questo rovinerà le possibilità di Graham di essere incluso nell'elenco per il vaccino antinfluenzale. Miggy cerca di aiutare Will a gestire la situazione con la dottoressa Dewan dandogli consigli. Intnanto Douglas si ammala e mentre delira per la febbre rivela accidentalmente a Rory che gli piace Poppy.

Graham e Rory devono participare alla recita scolastica su "Grease", con Graham come protagonista e Rory con una parte di secondo piano. Poppy e Angie vengono coinvolti e cercano di fare appello all'insegnante di recitazione per apportare modifiche. Nel frattempo, Will non è pronto a dire a Sophie che sta vedendo il dottor Dewan, così, segue il consiglio di Douglas e mente a Sophie.

Will incoraggia Angie a riscoprire la sua passione per la musica heavy metal prendendo lezioni di chitarra. Nel frattempo, il resto della banda riflette sulle passioni romantiche e Douglas corteggia la sua cotta con l'aiuto di Miggy, mentre Poppy si sente legata sentimentalmente ad un musicista.

Will è entusiasta di diventare rappresentante così da utilizzare questo evento come trampolino di lancio per la sua campagna contro gli smartphone e convincere i genitori a non comprare troppo presto i cellulari ai bambini. Per Dewan le cose non vanno come sperato... Nel frattempo, Douglas è convinto che il suo rivale, Mark, abbia rubato la sua preziosa penna...

When Owen shows up unexpectedly on Christmas Eve with a gift for Angie, she desperately seeks out help from Will finding a present for Owen last minute. While doing so, Angie learns how bad Will is at giving Sophie good Christmas presents, or so it seems. While Graham begins to doubt the existence of Santa Claus altogether, the group worries Miggy may still believe in him. Meanwhile, Douglas invites Poppy, who is dealing with her first Christmas without Rory, to compete in a series of cutthroat Christmas-themed competitions.

Will rifinisce gli ultimi dettagli della sua immagine pubblica prima dell'audizione per fare il meteorologo in televisione. Intanto Angie va in missione per ricevere delle scuse da Emma e Amy.

Will wants to get back together with Mia, but as their relationship progresses, he finds himself having to choose between the "normal" family he's always wanted and the new family he's created with Angie, Poppy, Miggy, Douglas and the kids. In order to get Will to come back to his senses about Mia, Angie kicks him off the babysitting grid and fills the spot with Dr. Mark, Douglas' rival dermatologist, much to Douglas' chagrin. Meanwhile, Graham is nervous to compete in the talent show and relies on Will to calm him down when he gets nervous on stage.

Douglas discovers that Amy is a math genius and is overwhelmed with how much time he has to spend to treat his daughters as individuals for the first time ever; this eventually leads to Emma moving into their private shed to get some space from Amy. Meanwhile, Graham makes a new friend at school, causing Angie to have to spend time with his new friend's mom, Nora, to Angie's chagrin. After Angie meets Nora in person and enjoys spending time with her, Poppy starts to grow jealous of Angie's newfound friendship.

Douglas agrees to babysit the kids on Valentine's Day, but when Graham finds himself in a Valentine's Day emergency and Big Red shows up unannounced, Douglas and Big Red band together to help Graham. Meanwhile, Will and Miggy celebrate "Palentine's Day" together - a day honoring the love of two friends - but when they run into Angie at her second job, they help her finish her deliveries so she can be with Owen on Valentine's Day.

When Poppy's ex-husband, Ron, gets serious with his latest girlfriend, Poppy has to deal with the reality of another woman helping to raise her kid. The secret gets out that Sophie has a crush on Graham, which causes a stir not only in the first-grade classroom, but also between Angie and Will. Meanwhile, Miggy gets cold feet after asking Douglas to remove his tattoo of Zara's initials, and Douglas has to help him realize that his relationship with Zara is officially over.

Seeing that baby Jack is about to walk for the first time, Miggy feels old and tries to recapture his youth by throwing an epic party. When the party doesn't go as expected, he insists that Poppy and Douglas stick around to help him. Angie's boyfriend, Owen, meets Graham for the first time, which doesn't go as well as they had hoped. When Will gets an opportunity to do the weather at 10:00 p.m., Rory tags along and causes drama on the set.

In a magical encounter at the Bachelor mansion, Chris Harrison bestows his wisdom on a frustrated Poppy and Angie, attempting to restore their faith in love and happy endings. Meanwhile, Will saves one of the kids at school from playground injury; and Douglas insists Will capitalize on the glow from this heroic act by getting as much attention from women as possible within its 24-hour window.

When no one bids on "Lunch with KZOP's Will Cooper" at the school auction, Poppy and Sophie scheme together to recruit Dr. Biscuits to bid on Will and play the role of his No. 1 fan. Meanwhile, Douglas attempts to teach a reluctant Angie how to cut back on extra spending and become more fiscally responsible.

To celebrate Angie's 30th birthday, Will throws a big party recreating Ozzfest, which Angie missed in her 20s; but when Angie assumes Owen planned it for her, awkward encounters ensue. Meanwhile, Douglas takes Graham shopping to help him find the perfect gift for his mom, Angie, for her birthday, but a distracted Douglas results in Graham buying a not-so-on-point gift.

Angie and Will dive headfirst into binge-watching a show called "JOUST!" together, but when Will starts to date someone new and ditches his TV-watching plans with Angie for time with his new love interest, Angie grows frustrated. Meanwhile, Poppy and Douglas bond over working on Rory's class president campaign until Poppy finds out about some of Douglas' shady campaign tactics.

After Will realizes he forgot to send in Sophie's deposit for space camp, he must woo the owner of the company, Lance Bass, in order to get her spot at camp back. Meanwhile, the twins' grandmother shows up wanting more time with Amy and Emma during the summer, causing Douglas to spin; and Poppy deals with unwanted old feelings for her ex Ron as she helps him plan his wedding.

After learning that Angie's ex Derek lives near Space Camp, Will convinces Angie to confront him about leaving her when she was pregnant, which results in a rowdy and awkward encounter between the three of them. Meanwhile, Poppy internally struggles with who she truly has romantic feelings for.