When she's caught kissing her new boyfriend in the elevator, Maya asks Finch not to tell Jack anything. But when Finch cannot keep the news to himself, Maya admits she has a new beau, but still says nothing of his age. However, when Jack comes across them at a local bar after work, he's stunned to discover that he and Maya's boyfriend Tom are nearly the same age. Meanwhile, Nina's flirtatious behavior sends a handsome window washer to the hospital after a nasty fall. Though Nina tries to hide her involvement in the accident from the police, she can't keep from telling Elliott. As Nina heads for the hospital to comfort the injured man, Jack notes the irony of Maya's dating Tom after complaining about his being married to a younger woman. As Maya and her dad seek understanding as to why they're at odds, Elliott weighs in on Jack's side, claiming that Tom is too old. And after turning to Finch for advice, Jack concludes that never getting the blessing of Allie's dad for their marriage has caused him to disagree Making an appointment with his father-in-law Frank, Jack is intent on getting his approval for his marriage to Allie. However, when Tom arrives unexpectedly to reveal that he's decided to break up with Maya, Jack gets to spend a few moments in Frank's shoes. And even though he tries to be magnanimous by offering his own blessing to Maya and Tom, Jack still finds it hard to accept. Finally, as Nina's hospital visit causes even more problems for the hapless window washer, Maya learns that Tom is breaking up on Jack's advice.