A 26-year-old person wrote to advice columnist Prudie, expressing concern about their father's upcoming remarriage. The father is set to marry a woman who is two years younger than the letter writer. The writer is worried the woman may be motivated by financial gain and is considering how to make their father see the potential mistake he is about to make. The writer’s concern centers on whether the new partner is genuinely in love or has other, more self-serving reasons for the relationship. Prudie and co-host Lizzie O’Leary discussed the concerns, noting that the letter writer may not have a close relationship with their father, which could influence their perspective. They acknowledged the difficulty in determining whether the woman is a "gold digger"—a term used to describe someone who enters a relationship primarily for financial benefit—or if she is genuinely in love. They suggested the letter writer could gently question their father about the relationship, focusing on how the new partner treats him and how he feels about the relationship overall. The discussion also considered the possibility that the assumption of the woman being a gold digger might be sexist. They emphasized that the letter writer should observe the interactions between their father and the new partner, and if necessary, frame any concerns around specific behaviors rather than making generalizations. They noted that if the woman is kind to the father and brings joy to his life, it could be a positive outcome for both him and the letter writer. The hosts also suggested that the letter writer consider the potential for a fun and positive relationship with the new stepmother. They acknowledged that adults, including parents, have their own desires and issues, and unless there is evidence of abuse, the father should be allowed to make his own choices. They advised the letter writer to be non-judgmental, so that if the relationship does not work out, the father does not feel defensive or need to hide it. They also suggested discussing financial plans with the father while he is still young and healthy. Finally, they concluded with a light-hearted note that weddings in the first five years post-college are often the most fun, suggesting that the letter writer might have a good party in their future.