Below Deck’s Cringiest Romance Fails

Below Deck Down Under

While watching Bravo‘s Below Deck series, you have likely winced once or twice during the various relationship scenes. Listen, I get that attractions can cause humans to be awkward, especially in the initial stages of a romance. From getting that first date to ensuring that this date is then successful, it’s all tricky.

While I can respect the bravery shown during these initial encounters of the heart, the methods to either secure a date, or, the planning of the actual first date, has sometimes induced second-hand embarrassment for the viewers of Below Deck. Insert the long-ago fired deckhand Danny Zureikat. Trying to secure a date with a guest of all people, Danny crooned, “When fish die, they swim towards the light. As they journey towards the afterlife, their souls will be filled with delight.”

Bless his heart, no.

Truly, watching these yachties try and turn their crushes into full-fledged relationships has sometimes been a lesson in what not to do. For your reading pleasure, here are Below Deck’s cringiest romance fails.

Jaimee Neale and Culver Bradbury


When Jaimee Neale joined the Below Deck Down Under Season 2 crew on Episode 9, Culver Bradbury immediately developed a crush. Luckily for Culver, Jaimee’s attractions were reciprocated, with the pair even sharing their first kiss shortly after on Episode 10. At this point, Culver ramped up his game, trying to lock down Jaimee as his girlfriend.

Culver first asked the stewardess to work with him on another yacht after filming. He then asked Jaimee to join him for a special date up on the yacht’s sun deck. When Jaimee arrived for this date, Culver handed her a homemade card, which was sweet, but this card also came with a pen. You see, inside of this card, Culver had asked Jaimee to be his girlfriend, and to answer, she needed to check either the yes box, or, the no box.

For the audience, Jaimee’s hesitations were felt. However, Jaimee checked yes, but, she then made fun of him afterwards in a confessional. Here, she compared Culver’s card to something that you’d find at the DMV, or even on a COVID-19 symptoms insert. Overall, Culver’s card was a miss for Jaimee, making this one of Below Deck’s cringiest romance fails.

Sierra Storm and Kyle Dixon

Kyle Dixon/Instagram

On Below Deck Season 4, Kyle Dixon felt an attraction for Sierra Storm. He began to pursue the stewardess despite the fact that he had a girlfriend on land named Ashley. To her credit, Sierra brushed off Kyle’s advances for awhile, but when his asks became borderline aggressive, she caved, saying yes to a fishing date. On this date, the conversation attempts failed, like, crickets chirping failed, so Sierra picked up her phone and began to text a guy from back home.

Kyle raged afterward, calling out Sierra for talking to another man on their date, even though he was the one officially involved with someone else. Kyle also proposed to Ashley shortly afterward, going on to proudly declare Ashley’s answer of a yes to Sierra and their crew. Spoiler alert, Kyle and Ashley’s engagement didn’t last long post filming.

This whole romantic journey was a mess, and the mostly silent fishing date was beyond awkward. Kyle and Sierra are therefore easily one of Below Deck’s cringiest romance fails.

Brianna Adekeye and Matt Burns

Below Deckkk/TikTok

Brianna Adekeye and Chef Matt Burns appeared on Below Deck Season 5. Here, Matt took one look at the stewardess and stated, “she’s beautiful.” Shortly after, the crew found themselves out to dinner, where both Matt and Brianna drank a ton. In their intoxicated states, Matt asked Brianna to join him on a date, and she said yes, but when she awoke the following day, she had zero memories of this conversation ever transpiring.

However, Brianna was up for a day off, so she agreed to the date once again. The pair then boarded a water taxi and headed off. Wildly, Matt was already tipsy, as he had imbibed in many drinks just prior, likely in an effort to calm his nerves. When arriving at Matt’s chosen location, things spiraled downwards, as Matt’s planned date was on a nude beach of all places.

While naked people walked past, Matt’s drinking caught up to him, and he basically passed out in the sand. When he came to, he called Brianna a “horrible date,” as she wasn’t answering his questions. She was done.

Courtney Skippon and Brian de Saint Pern

Shameless Strumpet/Instagram

Courtney Skippon and Brian de Saint Pern‘s boatmance on Below Deck Season 7 started off with a disastrous first date. Here, Brian asked Courtney to join him for drinks just prior to meeting up with their entire crew for dinner. The only problem was that Courtney was exhausted, and she did not want to be anywhere, save for her bed.


In addition to her tiredness, just prior to their date, Courtney’s dress had fallen into the toilet, and after deciding on another outfit, she didn’t have time to blow-dry her hair. As the underwhelming date began, the conversation fell short, and Brian told Courtney to smile (ew). Courtney explained to Brian that she was grumpy, noting this so that he wouldn’t continue to take her quietness personally. Brian then also turned quiet, making this a very awkward date.

However, even worse than this date was Brian’s joining of the toxic boys club. These men spent the season gunning hard for Kate Chastain and Rhylee Gerber, which saw Courtney being placed in the middle of confrontations often. Fortunately, Courtney’s verbally gifted skills shut down Brian and the other men beautifully when needed. That said, they are definitely one of Below Deck’s cringiest romance fails, and we hope that Courtney has since received many well-deserved naps.