On the Big Three's 37th birthday, Randall is determined to adopt a baby, but is convinced by Beth that he can honor William's legacy just as well by adopting an older child. Kate attempts to audition as a singer; she first leaves the audition because she sees only skinny women there, but decides to come back and go through with it. She is rejected, not because of her weight, but because of her inexperience. Kevin and Toby argue about how close Kevin is with Kate; Toby says he should be the one Kate goes to; Kevin admits that she originally told him about his father's death. In the past, Rebecca takes the Big Three to a movie, in the aftermath of Jack and Rebecca's argument. Later, Rebecca urges Jack to come home. Jack admits his alcoholism is out of hand. The aftermath of a house fire is shown, while Rebecca sits crying in her car, with Jack's belongings in a bag by her side.
Kevin is invited back for the 100th episode of The Manny, unbeknownst to Kevin, as way to embarrass him for the way he quit. Randall, Beth, the girls, Rebecca and Miguel all make the trip from New York to see the taping of this new episode. Randall begins to second guess fostering an older child because he is worried that whomever they end up with will have issues that are too complicated to handle. Kate gets an offer for her first gig, but because she does not want her mother to criticize or find fault with her performance, she asks both Rebecca and Toby not to follow her. They do, which leads to Kate confronting Rebecca about how she always treated her. When Rebecca looks to Toby for support afterwards, he makes it clear he is on Kate's side, which wins Rebecca's approval. Beth chats with Kevin after the episode is taped, and learns that Randall only risked failure once, in asking her out, which he did with Kevin's help. Beth reassures Randall they can go through with their plan, and with that new determination, Randall prepares to let his children know what they have decided to do. In the past, Kate speaks ill of Rebecca after she brings Jack home. This leads Jack to confess that both he and his father had a problem with alcoholism. Where Jack previously privately overcame his problem by boxing, he allows Rebecca to take him to an AA meeting, which he had previously avoided.
On the set of Kevin's movie, Kate geeks out over the fact that Sylvester Stallone is his co-star. She tells Stallone that his movies made her dad laugh, and shares how hard it has been for her since his passing. He and Kate reach out to Kevin about his grief over that event, but he brushes them off. Kevin's memories of his dad, and his grief over his passing, which he has suppressed for years, come to the forefront, affecting his performance in the scene being shot. Randall, who is bragging about how perfect their home is for a foster child, is thrown when he learns that one such individual, a young girl named Deja, is being brought to their home right away. In the past Rebecca has planned a romantic night for Jack, which allows him to open up about his problems. Meanwhile, Randall, in trying to reach out to his birth parents through an ad, is comforted by Kate and Kevin when a woman claims to be his birth mom for his family's money. In the present, we see Randall talking to Deja and explaining to her that her mother might be in prison for a long time. The episode ends with Kevin relapsing into what might be an old addiction to pain medication.
In the flashback we see that Kate and Kevin have chicken pox, but Randall is yet to be infected. After hearing that the children are sick, Rebecca's mom stops by expectantly. Rebecca, who has a strained relationship with her mother, is not happy about this. She is forced to confront her mother, when Jack also succumbs to chicken pox. The confrontation, which is about how different she treat Randall, ends up with Rebecca calling her a racist. In the present day, Randall takes his daughters and Deja bowling, which leads to a confrontation between him and the father of another young girl who insults Deja. Beth offers to help Deja do her hair, and the two bond as Beth does so. Randall admits to Deja that he has had a problem with nervous breakdowns and has taken up running to deal with his anxiety; he invites her to come with him the next time he does so. Kevin undergoes surgery on his injured knee, and continues to overuse his prescription pain pills. Kate is obsessed with getting in shape for a "singing gig", which turns out to actually be a visit to an OB/GYN for an ultrasound, revealing that she is pregnant.
In present day Kate finally tells Toby that she is pregnant, but orders him to keep all his excitement to himself, as she is very nervous about being pregnant at her age and size. After getting in a fender-bender accident however, she changes her mind and lets Toby proclaim to a random coffee shop, that they are expecting. Meanwhile, Kevin has run out of his proscription medication and frantically calls his doctor for a refill, which he is denied as it has already been filled once more than allowed. This affects his relationship with Sophie, whom he has promised to escort to a charity event and be auctioned of to raise money, as he is absent from the entire event. Randall learns that Deja has been to a violent foster home, which is why she doesn't like to be grabbed. In the past Jack takes Kevin and Randall on a camping trip hoping to improve their brotherly bond. In a flashback from Jack's childhood we learn that he has a brother and that they were in the army together.