Old charter guest Jack Freeman stirs trouble on Below Deck Mediterranean

Below Deck Mediterranean Season 10, Episode 3, aired on October 13, 2025, and featured a familiar face that surprised chief stewardess Aesha Scott.

The episode introduced charter guest Jack Freeman, who previously appeared on Below Deck Down Under.

Captain Sandy Yawn described him as a “prominent Sydney socialite,” and Aesha immediately recognized his name from her past experience.

As the crew prepared for the charter aboard Bravado, Aesha warned her stews, Kizzi Kitchener and Victoria “V” SanJuan, that the guest had “specific” preferences.

Jack’s requests included a white-themed dinner with a truffle-focused menu, a tasting menu for the following evening, and an assortment of water toys and wave runners. Chef Josh Bingham expressed concern about the complex meals, saying,

“With truffles, you have to put them with stuff that really works with them, or they can taste kind of flat.”

The episode followed the team as they tried to meet the guests’ expectations while managing challenges both in the galley and on deck.

From unpacking an overwhelming number of suitcases to a late-night food request, the crew navigated a demanding charter with patience and professionalism.

A familiar face returns to Bravado in Below Deck Mediterranean

When Aesha discovered Jack Freeman would be joining the charter, she immediately remembered his previous appearance on Below Deck Down Under Season 2, Episode 3.

During that trip, Aesha recalled that Jack requested “a piñata actually made of chocolate” and asked that a deckhand breathe in his ear as part of a playful moment.

In Below Deck Mediterranean, Aesha told all her stews to prepare for his “very specific” preferences.

Upon boarding Bravado, Jack announced, “I will warn you, I’ve brought a lot,” referring to his luggage. When Aesha asked how many, he replied,

“Seven [suitcases].” The stews quickly realized the scale of the task, as one suitcase alone contained 40 pairs of shoes.

“I’ve never seen this many clothes in my life,” Kizzi said while unpacking.

As the charter continued, the crew worked to deliver the guest’s requested experiences, from the elaborate dinner setup to personalized service. Aesha shared,

“Having guests like these, they’re very specific with what they like, so I hope that Kizzi and V can keep up and deliver the standard which I really need to give them.”

The demanding start to the charter set the tone for the episode, highlighting how the team coordinated to meet expectations under tight schedules.

Late-night request tests the crew in Below Deck Mediterranean

After a successful first-night dinner featuring truffle-inspired dishes, the crew thought the evening was over.

However, Jack made a surprising late-night request for “Sichuan chicken.”

With chef Josh already asleep, stew Kizzi asked,

“Is there any alternative?” but Jack insisted, “All I can think about is chicken.”

Unsure of what to do, Kizzi asked deckhand Christian Trimino to help look up the recipe.

“I need soy sauce, salt, pepper, and flour,” he said while searching on his phone.

Kizzi hesitated, not wanting to use the chef’s supplies without permission. “I honestly don’t want to use any of chef’s stuff and then him be like, ‘I needed that,’” she said.

Bosun Nathan Gallagher advised against cooking at that hour, warning,

“You’ll give him food poisoning.” Instead, Kizzi found leftover chili from the crew lunch and decided to serve it as a substitute, noting, “I think he’s too drunk to even notice.”

When she finally brought the food to Jack’s cabin, she found him already asleep. “Are you joking me?” she exclaimed.

The moment captured the unpredictable nature of luxury charters and the challenges faced by the crew in balancing professionalism and guest satisfaction.
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