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Tensions within the crew run high on the final night of the charter season; Timothy Sykes micromanages the crew; Jen tries to be on her best behavior; Nico summons the courage to end things with Brianna; Jen attempts to mend things with Kate.

Below Deck

The Champagne Campaign

Timothy Sykes returns and cannot live without his Wi-Fi, causing Kate and Captain Lee to feel the pressure; Jen is scrutinized after she upsets the entire crew; Nico struggles to make a decision about his relationship.

The One Where Jen Loses Her Mind

Capt. Lee tests Matt as he removes Bruno from the galley and joins the women for dinner; Jen and Kate's working relationship deteriorates; Kyle and Jen grow closer, but Kyle has ulterior motives; Jen reaches her breaking point.

You Don't Mess With the Primary

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Capt. Lee invites a special guest to come aboard; the crew is surprised by a familiar face; an all-female charter proves to be a handful for Kate and Capt. Lee; as Matt continues to struggle, Capt. Lee takes action to prevent further embarrassment.

Only Doing It for the Money

Weather conditions force Capt. Lee to make a touch choice; an accident puts Nico in jeopardy; Kate tries to entertain land-locked guests; Brianna grows weary of Jen; Matt is back in hot water with another restaurant owner.

King Come-On-I-Wanna-Lay-Ya

Crew members have their hands full when eight big Texas personalities come on board; Matt attempts to step up his cooking game; Nico tries to demonstrate he is better bosun material than EJ; Kate tries to protect Jen from lecherous guests.

Hot Mess Express

Nico and Brianna grow closer in spite of Nico's girlfriend back in Chicago; unexpected news sends Matt into an alcohol fueled day off; Kate challenges Jen and Brianna to a stewardess speed test with unexpected consequences.

Under Cover Boss

Leigh Anne Tuohy, the inspiration for Sandra Bullock's character in "The Blind Side," and her friends prove to be a challenge for Matt's culinary skills; Jen fails to adhere to the yacht dress code; Matt reconnects with someone from his past.

Blindsided

Nico is pushed to his breaking point under the leadership of boson EJ; Matt continues to unravel after his date with Brianna, which causes problems for Kate; Capt. Lee makes a staffing decision.

100 Feet From Catastrophe

Capt. Lee makes a decision regarding the crew's re-configuration; Matt and Brianna mistakenly go to a nude beach; Jen grows weary with unfair treatment; Kate plans an anniversary surprise that fizzles; criticism sends Matt spiraling into shame.

Cool Beans

During their night off, Jesus and Kate get to know each other; Chris Brown makes a pass at Brianna; Nico marks the 3-month anniversary of the passing of his brother; a group of fun charter guests arrive ready to party.

Kate Goes to Church

Chris Brown's decision to take a nap lands him in hot water; the new guests prove to be a handful; Kate meets a cute sailor and visits him on his boat; Matt faces his first challenge of the season with sushi dinner and a tequila pairing.

Jesus Saves

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Young and single crew live, love and work together aboard a luxurious yacht.

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Tensions run high as Kate and Nico continue to struggle operating with a crew of newbies; the crew welcomes their first charter guests; Capt. Lee finds himself having to get more involved in troubleshooting problems.

S5 E2 | It Ain't Easy Being Green