S1 E5: Even Playboys Get the Blues

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Even Playboys Get the Blues

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Dan and Jared’s friendship continues to grow as Jared properly introduces Dan to the Blues. Listening to a local singer, Dan learns about Jared’s war experience. Leaning into his depression, Dan inventories his situation, rations his points, and attempts to make amends.

More from season 1

E1: The Arrival

Ambitious executive Dan Kinney arrives in Florida for business only to discover that his big financial investment has tanked, setting off alarm bells with his firm, family, and authorities. In denial and locked out of his accounts, Dan relies on travel points to stay at a posh beachside resort until the scandal blows over. He charms guests and irritates employees until a drunken outburst threatens to land Dan on the streets.

A man in a suit sitting indoors covers his face with one hand, looking stressed. A blurred figure is in the foreground, and a large plant and staircase are visible in the background.

E2: The Age of Aquarium

Desperate to fix his situation, Dan enlists a spy to uncover intel from his New York firm. Under strict rules from the hotel manager, he sneaks out to explore St. Pete/Clearwater. At the local aquarium, a sexy staff biologist enlists his help in a unique animal interaction.

A man and a woman are sitting closely together, both smiling softly. The woman has her head resting on her hand, while the man leans in slightly. They are indoors, with blurred shelves in the background.

E3: Dan Kinney’s Holistic Detective Agency

As the SEC investigation intensifies, Dan is focused on following the money until bartender Jared enlists him for a geocaching challenge. While exploring St. Pete/Clearwater, Dan rediscovers his competitive side...and an idea that may prove his innocence.

E4: The Paper Chase

Eager to get his old life back, Dan attempts to meet up with a colleague at the hotel convention, but a mix-up at the bar has him chasing swag bags all over town. Dan runs into Amy at a local club before a revealing conversation with Stanford Demmings.

A man with wet hair lies in a bathtub, looking upwards. One hand is raised near his face. The background features a black and white checkerboard-patterned tiled wall.

E5: Love Boat

The event takes an unexpected turn while crossing the Tampa Bay via ferry.

A wedding ceremony on a boat's deck under a clear blue sky. A couple holds hands between an officiant and two guests, one holding a bouquet. The ocean stretches into the horizon, creating a serene backdrop.

E6: Red Card

After Dan apologizes to his estranged brother, Paul hits him up for babysitting his precocious niece and nephew. Dan’s childish prank at a Tampa Bay Rowdies’ soccer game results in panic and payback.

A man stands smiling with two children, a girl and a boy, in front of a large green and yellow sports banner. The girl is looking up at the man while the boy gazes upwards. They appear to be outside in a lively setting.

E8: Paradise Tossed

Season Finale. As the SEC investigation comes to a close, Dan is faced with a major life decision and devastating news from his family.

A person stands on a dimly lit beach at night, surrounded by faintly illuminated buildings and palm trees. The scene is moody, with soft lighting highlighting the figure's clothing.