Below Deck Charter Guests’ Most Inappropriate Requests

Jessica More
(Photo by: Karolina Wojtasik/Bravo/NBCU Photo Bank via Getty Images)

Throughout the Below Deck franchise, money is king. Within the primary charter guest’s belongings, a fat envelope filled with tip money resides. Therefore, once the affluent passengers step onboard their given yacht(s), the crews hard work begins. Working in tandem to gain possession of said envelope, the interior and exterior departments have one job to do—literally everything.

Often, the charter guests come aboard with tall orders. Over the years, requests that range from demanding menus to over-the-top themed parties have all transpired. A handful of times, however, the guests demands have bordered on inappropriate. These asks have seen the crews within placing aside their prides, and in rare instances, even saying “no.”

Insert Countess Luann de Lesseps singing “money can’t buy you class, elegance is learrrnnnned, my friend.” Sing on as we rehash the most unreasonable, inappropriate requests that the Below Deck crews have had to endure thus far. And also, insert us as Rocky Dakota jumping overboard, because all of these deserve her level of nope.

The Guests Who Wanted To Unbutton Jack Stirrup


Jack Stirrup appeared on Below Deck Mediterranean during Season 4, and for his appearance, the drunk cougars were thankful. As Jack was on watch in the wheelhouse, the cougars entered.

Here, a charter guest stated “what if I unbuttoned that..” while reaching towards the buttons on Jack’s uniform. Luckily, Captain Sandy Yawn quickly entered in and shut down this guest’s inappropriate request, asking them to not “molest” her crew.

The Married Couple’s Proposition

Watch What Happens Live/YouTube

In Below Deck Season 5, Stewardess Jen Howell did not get away as easily as Jack did above. Jen was actually propositioned many times in one charter. Calling Jen into her cabin, a guest first removed her shirt in front of the shocked stew before shutting her door. Through this closed door, the cameras picked up the guest explaining to Jen “you’re not allowed to leave…I’m giving you what you want…give me a hug…my husband likes you.”

Realizing that the married guests were propositioning her, Jen rebuked the request and went straight to her department head, Kate Chastain. At first, Kate passed these behaviors off as drunken antics. However, Jen’s backside was then grabbed during dinner, as the guests commented on how she was “cute as f**k.” The next day, Kate handed Jen a necklace with a whistle on it, for if she felt unsafe

Recently, Jen appeared on Watch What Happens Live. Here, she reflected on her past experience. Before thanking Captain Lee Rosbach for his excellent leadership, Jen revealed that she still toils in the yachting industry, and that work remains to be done regarding acceptable behaviors on yachts.

The Nude Cruise


When the founder of the film site, Mr. Skin, made his way onto Below Deck Mediterranean in Season 2, he had one request—to shoot content for his Naked News webcast. The entire crew had to therefore face constant nudity onboard. In addition, Chef Adam Glick was tasked with making a breast cake, which the stews served in bikini-adorned shirts, while Malia White had to help a nude woman onto a paddleboard. This entire charter was a lesson in inappropriate requests.

Naked Sushi


Speaking of nudity, Below Deck Sailing Yacht‘s Season 4 saw Gary King being adorned by sushi for the charter guests to consume. BRB, gotta gag. While this was nasty for many GARY-CENTERED reasons, this wasn’t the first time that this inappropriate ask took place. The first instance of this request actually came during Below Deck Season 8.

Here, the young, wealthy co-primaries Dax and Max, alongside their 20(ish) year old guests, had one goal in mind; to drink. Champagne, margaritas, Jell-O shots, you name it, they wanted it. Oh, they also had another request—to eat sushi off of a naked woman. (The model was paid and consented, all good on that end).

As Chef Rachel Hargrove tried to explain the delicate, expensive cuts of fish within each roll, the guest’s interests were only spent on snapping photos and grabbing at the model adorned with sushi. These guests then requested more Jell-O shots, which cannot pair well with fish, but maybe that’s just our less than wealthy palates talking…(it’s not). For the record, Max apologized for this storyline, placing some of the blame on production.