In the past, we see a blissful morning that Jack (Milo Ventimiglia) and Rebecca (Mandy Moore) spend in bed. Afterward, he takes her to her parents’ home and her father, Dave (Tim Matheson), asks Jack to go out for a round of golf with him. Jack reluctantly agrees. He doesn’t have the clothes or clubs he needs for the outing and feels embarrassed when Rebecca’s dad insists on buying him both. To make matters even more awkward, some golf friends offer to let Jack and Dave join their double. They talk shop and Rebecca’s dad pressures one of his friends to give Jack a job offer. Jack grows uncomfortable and so he starts drinking—a lot.
Afterward, Dave confronts Jack about his drinking and says he should have taken the interview. Dave tells Jack that his dad was poor, too, but he worked hard so he could join a nice country club and create a nice life for himself. He tells Jack that he sees Rebecca’s future clearly, too, but he wonders if Jack can envision himself in this world.
When they arrive back at Dave’s home, Jack tells him that he’s going to marry Rebecca and Dave responds by saying that he’s never going to be good enough for her. They square off against each other until Rebecca comes outside and tells Jack she’ll take him home.
In the more recent past, when the Big Three is 11 or so, Jack sees Randall (Lonnie Chavis) watching Tiger Woods on TV and offers to take him golfing. They chat on the putting green and Randall tells Jack that he’s the first black kid to ever be on the debate team. Jack tries to reassure him that he’ll be successful no matter what and tries to relate to him, saying that people used to make him feel uncomfortable because he was never rich enough or had the right job. Randall grows frustrated because his father doesn’t understand that he’s talking about race, not privilege.
Later, Randall tries to explain it to his dad. Even though Jack feels uncomfortable on a golf course, it’s worse for Randall. At one point, he wouldn’t even have been allowed on the course because of the color of his skin. Randall also points out that Jack and Rebecca let him quit karate, where there was a strong black community, but they haven’t allowed him to quit traditionally white sports.
Afterward, Jack tells Rebecca what happened, and she tells him that Randall is still trying to find his place in the world. So, the next day, Jack tells Mr. Lawrence (Brandon Scott) that if his son is asking complicated questions about his role in society, he’d appreciate a heads up. He also invites him to dinner at the Pearson home.