Cringiest Below Deck Moments

Below Deck Season 7
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Below Deck has seen many memorable moments, although the franchise has also had its fair share of cringey moments. As every Below Deck fan knows, it is not uncommon for the charter guests to have ridiculous and outlandish requests. These requests often come at the expense of the crew members dignity, as they are sometimes forced to make a fool of themselves for the guests entertainment.

Apart from requesting cringey things from the crew, the guests also have no problem partaking in the embarrassment themselves. At times, the charter guests act downright humiliating, and they have been responsible for many cringe moments on Below Deck throughout the years.

Rocky’s Mermaid Act During The Greek Party


One of the cringiest moments on Below Deck was during Season 3, when the charter guests requested a Greek-themed party. While there was nothing wrong with this theme in itself, it was poorly executed, with the guests just throwing on white togas and leaf crowns.

The real cringe factor, however, was 3rd Stew Raquel “Rocky” Dakota dressing up in a mermaid costume. Rocky not only dressed up, but jumped into the water and flopped her fake tail around. The guests loved it and clapped for Rocky as they looked on, but the entire situation just seemed unnecessary. The party was at night, so Raquel actually going into the water did not seem like the safest idea either.

Charter Guest Dolores’ Late Night Swim


Dolores was one of the most chaotic charter guests in Below Deck history, who also provided viewers with one of the series cringiest moments. During a charter on Season 8, Dolores got too drunk and decided to take a dip in the ocean. One of her friends tried to derail her from doing so by joking that there were sharks in the water, but Dolores was determined.

Captain Lee Rosbach was infuriated, and rightfully so. Dolores choosing to be irresponsible was completely disrespectful to Captain Lee and the rest of the crew. The entire scene was just so cringe to witness, especially after Dolores embarrassed herself further by refusing to swim back to the boat.

The Foam Party


Season 3 was a rough one when it came to cringiness, as the infamous foam party also makes the list. Charter guest Steve was excited to participate, although none of his fellow guests seemed to have any interest in it. This led to Steve jumping around in the foam alone and shouting for them to join him, which was just awkward.

Eventually, the crew felt bad and felt obligated to join Steve so that he was not partying by himself. 2nd Stew Amy Johnson got particularly into it, and did her best to help Steve have a good time. Between the bizarre choice of party theme and Steve’s dull friends, this scene was just too cringe to watch.

The Charter Guests Comparing Chef Adam’s Food To Dog Food


Below Deck Mediterranean Season 3 featured one of the most awkward dinners the show has ever seen. Chef Adam Glick prepared a pasta dinner for a group of guests, which he served to them in a bowl. The guests were immediately dissatisfied upon seeing the presentation, and even went as far as to compare it to dog food.

This group of guests was particularly whiny, and it was difficult to watch them disrespect Adam’s food so casually. One guest even went as far as to ask Adam for a grilled cheese, after she claimed she could not eat the pasta as it was not up to par. There’s nothing wrong with a good grilled cheese, but that was just absurd!

Kelley Johnson Reluctantly Agreeing To Go Down The Slide With A Charter Guest

Raquel Dakota/Instagram

To top off the list of the cringiest Below Deck moments ever, how about that time when a charter guest begged Kelley Johnson to go down the slide with her. It was clear that Kelley felt uncomfortable, but he proceeded after Captain Lee gave him the ok.

To make things even worse, the guest had the audacity to ask Kelley to remove his shirt for the ride. Kelley firmly said no, which the guest did not seem too happy about. The entire reaction was just difficult to watch, as the guest completely did not care that she was making Kelley uncomfortable.