Cringiest Times When Below Deck Charter Guests Made a Fool of Themselves

Kate Chastain on Below deck
(Photo by: Karolina Wojtasik/Bravo/NBCU Photo Bank via Getty Images)

Bravo‘s popular Below Deck series has housed every kind of guest imaginable amongst the franchise’s given yachts. From charter guests with inappropriate asks and behaviors to relaxed and low-key vacationers, this show has truly seen it all.

For example, when supplied with copious amounts of liquor, some guests have gone overboard. Yes, literally, as was first seen in Below Deck Season 8 with our spirit animal a charter guest named Delores. Crazily enough, this quick method of exiting a yacht occurred a second time on Below Deck Down Under Season 2. Here, Brandon and Kristyl’s drunken nighttime leap took center stage, angering the crew in the process.

Mostly, the charter guests behaviors have been mild, with small touches of wild here and there. Thankfully, the ever-present camera crews are always onboard, catching all of these moments in real time for the viewers to later watch (and silently judge). Here are a few of those cringey times, highlighting the Below Deck charter guests who made fools out of themselves while onboard the various yachts of opulence.

The Whiskey Wimps

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Michael Durham came onboard Below Deck Season 9 with a few of his colleagues. Stating that he had “an appreciation for fine whiskey,” his preference sheet also noted an eagerness to “get wild.” Michael’s group was already three sheets to the wind by the time that they got to the yacht. It was later learned that they had polished off an entire bottle of Titos beforehand.

Justin Richards, one of Michael’s colleagues, requested a thermos for his bourbon. He was also spewing aggressive statements right from the jump. When offered a cold towel, he answered by saying, “I’m gonna slap somebody with a towel.” During a tour of the yacht, Justin told his co-worker Terri that he’ll kick them “down the god**n stairs.”

At the end of the tour, Chief Stew Heather Chase instructed the group to “come down this way.” Justin replied “I will do whatever the f**k I want.” Continuing to drink for the next several hours, Justin requested tequila during a fancy whiskey tasting. His group recoiled, causing Justin to head down to the swim deck to dine alone, like a toddler.

Furthermore, his anger became directed towards the crew when they attempted to deescalate his behaviors. To Heather, Justin replied, “No, go f**k yourself, go throw yourself off the boat.” Eddie Lucas then became involved, and all parties were escorted to bed. The next morning, Captain Lee Rosbach chastised Justin with Michael present, telling them to “get their s**t together.”

They did, but they were such drunkenly cringe charter guests that after they exited, the crew could still be heard celebrating, relived to be done.

“Happy Times”

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Roy Orbison Jr. is a twice returning guest on Below Deck Mediterranean, but it was his second-go-round in Season 6 that saw him making a complete fool out of himself. At dinner, an intoxicated Roy started saying “happy times,” drinking anything that he could get his hands on. Roy began to slur, with production adding in hysterical, gibberish subtitles to match his attempts at speaking. He also made a mess in the bathroom, which his friend had to tell the crew about so that it could be cleaned.

All of that said, Roy was charming, never threatening or crossing boundaries, so the crew was easily able to laugh off his “happy times” antics. His family for the most part could as well, but it’s likely that when watching back their charter, Roy himself felt a bit cringe.

Fingerprints On Captain Lee’s A**

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Charter guests Helen Hoey and Richard Fiore made their second Below Deck appearance on Season 7, just after coming onboard in Season 6. After receiving large glasses of wine and a tour of their new yacht, Helen and her friend Kelly ventured into the bridge to invite Captain Lee to dinner.

Immediately, both of the women placed their hands on the Captain, with one stroking his back and the other petting his arm. “He is Captain Zeus,” they declared while giggling, as Captain Lee calmly stated that he was “flattered.” Kelly’s hand then moved south, landing on Captain Lee’s bottom. “I mean, I’ve got more fingerprints on my a** than the FBI,” he joked in a later-shot confessional.

Were the roles reversed, more than just nervous laughter and snarky asides would have followed. Therefore, we can’t help but hope that in watching this back whilst sober, Helen and Kelly cringed at their behaviors.

The McDonald’s Low (Yet Great) Blow

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Entrepreneur Karim Gharb and his Bitcoin mogul friend Eunice Wong gave the Below Deck Down Under crew a run for their money during Season 1. Karim was bougie, asking Chief Stew Aesha Scott to redecorate his cabin, as the accessories were not aligned to his tastes. “If you’re that bougie, buy your own bloody yacht!” Aesha exclaimed in a confessional.

It was Eunice, however, who brought the highest cringe factor. That said, I’m not mad, as her disgust was aimed at Chef Ryan McKeown who needed a good humbling. Screwing up her face in disgust after her first bite of lunch, Eunice asked “Can I have McDonald’s?” At dinner, Ryan served raw fish, prompting Eunice to ask, “Can you just give me some scrambled eggs?”

Watching these nouveau riche charter guests pretend to have good taste by criticizing everything was cringe. They definitely made a fool out of themselves on-air, but again, at least Eunice’s behaviors were well-aimed.

TELL US – CAN YOU THINK OF ANY OTHER CRINGEY, EMBARRASSING MOMENTS DISPLAYED BY BELOW DECK CHARTER GUESTS?

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