Once Jack and Rebecca get together, they are inseparable — and insatiable. However, Jack is still having trouble with Rebecca’s parents, especially her dad. Rebecca’s father asks Jack to go out to the country club with him to go golfing. Jack denies him at first but Rebecca encourages him to take this chance to get to know her dad better. On the golf course, Rebecca’s dad is as condescending as ever. “There’s hope for you yet,” Rebecca’s dad says. That’s when Jack heads straight for the alcohol.
Just when things can’t get any worse, Rebecca’s dad continues to stick the knife in. “Do you see yourself here?” he asks Jack. Regardless of whether or not Jack is in the picture, Rebecca’s dad thinks that he’s going to be walking Rebeccadown the aisle at the country club. When Rebecca’s dad and Jack arrive back home, Jack tells him, “I’m going to marry your daughter, Dave.” Dave replies, “You’re never going to be good enough for her, Jack.” Even though Jack stumbles and falls down right in front of Rebecca, her father’s statement couldn’t be any less true.
In the present day, Kate and Toby’s relationship isn’t exactly hot and heavy after baby. Toby asks Kate to go away with him for the night. At the hotel, things don’t get off to the steamiest start. “I just have a lot on my mind,” Toby says to Kate in bed. Kate asks, “Is it me? Are you still attracted to me?” Toby swears that’s not it and brings up their earlier conversation about giving away Toby’s pants. Toby says that Kate’s comment got in his head and he feels like Kate was questioning whether or not he can keep the weight off.
Despite his less-than-stellar time at the golf course with Rebecca’s dad, Jack tries to make sure this isn’t the case with Randall. Randall talks about how Mr. Lawrence says he’s breaking barriers at school by being the first black student on the debate team. Randall is aware that the path to success isn’t going to be easy for him. Jack assures him he’ll be able to do whatever he wants to in life. Jack talks about how he felt like he wasn’t welcome at country clubs back in the day because he didn’t make enough money or have the right job. He admits he stopped playing golf because he let people like Rebecca’s father get to him. “That’s not what I’m saying, dad,” Randall says to his father. Jack says he’s going to do whatever it takes to make sure no one holds him back.
Later, Randall says he doesn’t want to play anymore. Jack wants to know why. “You just don’t get it,” Randall tells his dad. “You felt uncomfortable at a golf course and I probably wouldn’t have even been allowed on it,” Randall says. Jack apologizes for what he said. “I don’t look at you and see color. I see my son,” Jack says. Randall replies, “Then you don’t see me, dad.” Jack finally sees Randall at this moment. He tells Randall that he’ll start to listen better and lecture less. He does say to play the game, even if it means playing up to the competition or play down. Randall takes this advice and remembers it well into the present day. Later, Jack goes to Randall’s school and asks Mr. Lawrence over for dinner. He wants to know more about the man who is having such an impact on his son’s life. Toby and Kate rekindle the fire between them and she reassures him that he can keep the weight off.
Kevin is stalking Zoe on social media and Nicky has no idea what social media even is. Zoe has moved on with a “hot guy,” apparently. At the gym, Kevin tells Cassidy about Zoe and how she didn’t want kids. This surprises Cassidy. “You don’t seem motivated,” Cassidy says. These two flirt up a storm, but Kevin ends up asking one of the girls at the gym out to get back out on the dating scene.
When Kevin and Donna are walking back to Kevin’s place, Cassidy shows up. She had a fight with Ryan and she’s feeling down about it. “I wouldn’t want to be with someone as screwed up as me,” she says. Cassidy walks over and kisses Kevin. They break off the kiss and she begins to walk out but he tells her to stay. They end up having sex together and keep it a secret when Nicky shows up to make a sandwich. Well, things just got more complicated.