Kate, Toby (Chris Sullivan) and baby Jack are back home, but the tension between them is still palatable. Toby feels it and asks Kate what’s going on, so she admits that she saw the text from Cara, his CrossFit friend. (Ya know, the one that says she’s here if Toby needs to talk about his relationship issues?) Toby assures her they’re just friends and she decides to let it go. They hug and she says she just wants to get past this.
Meanwhile, sticking to his promise of landing a wife and a baby ASAP, Kevin hires a matchmaker and goes on a plethora of dates. One’s too smart for him and one’s even racist.
In order to get past their relationship lull, Kate decides to throw Toby a Jimmy Buffett themed surprise party and enlists Kevin and Madison (Caitlin Thompson) to help. Once they find the perfect ugly Hawaiian shirt for Toby to show off in front of his CrossFit friends, Kevin and Kate go to get a cup of coffee. He tells her he’s giving up on his match-making service and going to rely on the universe to find him a wife. And that’s when he spots a woman named Lizzy (Sophia Bush) who he can’t take his eyes off of.
They meet, hit it off and go to have lunch. Their chemistry is incredible but then she drops a bomb: She lives in Chicago. But Kevin is already smitten, so he tells her he’d love to whisk her off on a proper L.A. dream date. He says he has to make some calls and since she told him she loves John Legend, we suspect that’s probably who he’s about to call. And, yep, it turns out Kevin was able to secure the entire Hollywood Bowl and a private performance with John Legend just to make Lizzy smile. Damn, Kev.
While Kevin’s falling in love, Kate and Toby are falling apart. They barely speak at the surprise party and afterward they have a come to Jesus. Kate asks him why he switched gyms without telling her and he admits that Cara his CrossFit friend tried to kiss him. He wasn’t into it though and got away fast so that nothing more would happen. But this doesn’t explain why Toby has been avoiding Kate and their home. Finally, he says the reason he doesn’t want to be home lately is because Jack’s condition makes him sad. Kate doesn’t know how to react to this—she’s hurt, she feels alone, she’s offended. So, she takes Jack and goes into the other room.