‘Below Deck’ Bosun Ben Willoughby Teases Trouble Waters Ahead: “I Had Hard Conversations That Didn’t Go In My Favor”

After one season and some change, Below Deck‘s Ben Willoughby has finally received his long-awaited and well-deserved promotion to bosun! Former bosun, Jared Woodin, had been causing issues between departments through his erratic behavior and sloppy leadership , while Willoughby had been quietly biding his time and establishing himself as a mentor to deckhands Kyle Stillie and Sunny Marquis. When Captain Kerry Titheradge was forced to fire Woodin when he berated Stillie after a night out, Titherage knew Willoughby was the right person to replace him.

Though, Willoughby was the first to acknowledge that Woodin was going through a tough time. “He had a lot on his plate. You got to give him that,” Willoughby said generously. A skilled and steady yachtie, Willoughby was eager to step up and take charge as Bosun. The promotion felt natural to Willoughby because Chief Stew Fraser Olender would “often come to me as opposed to Jared for a lot of things.” “Fraser definitely saw me in that bosun role,” said Willoughby. However, Willoughby did tease “friction this season” between him and his frequent co-worker Olender. “I had to have hard conversations that very much didn’t go in my favor a lot of the time,” admitted Willoughly simply.

In addition to navigating the responsibilities of his new role, Willoughby also had to figure out how to traverse his flirtation with Marquis, which started when they were both deckhands. “It’s the first time I’ve dated someone in the same department,” said Willoughy, whose Season 10 romance with Stew Camille Lamb ended badly. “It was very difficult having to step up in a role and be someone’s boss rather than an equal.” Viewers can trust that complications arise between Willoughby and Marquis.”The relationship side of things [is] very much on the back burner for me,” confirmed Willoughby.

Willoughby stopped by the Page Six studio to speak to DECIDER about his new role, what’s to come this season, and the exits of Woodin and stew Cat Baugh in the same episode.

DECIDER: Ben, you’re in an elite group of yachties who have done multiple seasons on Below Deck. How does it feel to be back for round 2?

BEN WILLOUGHBY: It’s really cool to see the guys doing their first season, which I can relate to. I was like: “Oh yeah, I did that in my first time. That kind of sucks. I know where you’re coming from.” Especially with Sunny, to be honest. She was coming in gun hot, trying to show what she could do and was really excited. I did that last season with Ross McHarg. Captain Kerry was my third captain on the same boat, so I feel like I had got that advantage up my sleeve.

We love Captain Kerry! What was your reaction when you heard he was taking over the St. David?

It was comforting to hear a familiar voice in the Aussie accent. That was fantastic. He’s a bit shorter than I thought he was [laughs]. For my first season, Captain Lee and Captain Sandy split the time unexpectedly, so it was nice knowing that there was going to be one captain on for the whole season. However, I still had to prove myself to a new captain. It was like starting from square one again.

You seemed wary of Jared from the very beginning. Do you remember the first red flag you saw from him?

It was him dropping the anchor in the port. That was the biggest thing for me. I was like: “Dude, that’s the first thing you don’t do. You’ve got to let the captain know straight away. Anything you’re doing with heavy machinery, especially when you’ve got some green deckhands on the boat, you don’t want to be teaching them bad habits from the start.” Right then, I knew he wasn’t going to last. I feel like I’m a good judge of character. Speaking to him from the get-go, I knew he was a small boat captain. There are a lot of things that you miss when you are a small boat captain coming on to the super yachts. You tend to have lower standards. I knew I just had to bite my tongue and wait for my moment because it had got to come someday, right?

And it did.

And it did.

I do have a serious question, though. Do you think American bosuns are at a disadvantage because they aren’t familiar with the metric system?

Yes. I was so glad I was not in Jared’s shoes when he was trying to call distances. But you know what? I don’t know the Imperial system all that well. When I was working with Captain Lee, I had to think on my toes. I was like: “Okay, meters to feet, you kind of times it by three or divide it by three roughly.” That’s what I was going off. You just kind of fake it till you make it. However, captains should know both. Jared’s a small boat captain, so I don’t know why he didn’t know both. That was another red flag I saw.

There were leadership issues with Jared from the beginning, but the rest of the deck crew really seemed to bond quickly. What was it like rooming with Kyle this season?

I don’t think I could have asked for a better roommate than Kyle. I had Tony [Dua] last season, who was fantastic. Kyle was just my man. He’d worked and lived in Australia before, so we had a lot of common ground there to build on.  He didn’t really give a shit about anything [laughs]. That’s very much the Australian way. We just got on straight away. If I had roomed with anyone else, I don’t think I would have had as fun of a season.

Speaking of someone you also had some fun with this season, I want to talk about Sunny. You two seem to have instant chemistry. What first stood out about her to you?

My relationship with Sunny marked the first time I’ve dated someone in the same department. Those were uncharted waters, excuse the pun, for me. She wasn’t afraid to get her hands dirty, which is necessary for someone who actually works on deck. She wanted to jump in and help out and learn and progress in her career. I’m not saying that the interior team doesn’t, but they’re more, I would say, delicate. That’s probably the way to put it. Her work ethic is what drew me to her. And she’s gorgeous too, by the way.

I want to get into the Jared drama of it all. Could you sense his time on the charter was nearing an end?

He had a lot on his plate. You got to give him that. He was struggling to find a way to have a relationship with his daughter who he’d never met face-to-face. That’s something I can’t relate to, so I didn’t really know what was going through his head there. He was managing a big team, and he as struggling a lot with a new captain and a new boat. He was just very much out of his depth.

Did you sense that the night that he was wasted and kept berating Kyle was going to be his last on the boat?

Oh, I think he was done after the end of charter two when [Stew] Barbie [Pascual] went off on him. Like, I said, I’m a good judge of character, and I was just waiting for people to see what I saw. Once Barbie noticed there was something off, it was just a domino effect. Plus, I think Jared was a bit jealous of Kyle since he and Barbie were getting closer. Once his true colors came out, it eventually led to Captain Kerry having to make the decision to fire him.

You did not hesitate to accept the role of bosun when Captain Kerry offered it to you. How eager were you to prove yourself to him and the rest of the crew?

I felt like I was already in the bosun role, to be honest. Fraser definitely saw me in that bosun role. He’d often come to me as opposed to Jared for a lot of things. Nothing really changed in that sense. I was already teaching Sunny and Kyle how to operate the anchor. They didn’t know how to operate machinery. They couldn’t drive the tender either.

So, it was me teaching a lot of the stuff while Jared was doing whatever he was doing and being his own worst enemy. Since I was already doing so much with the team, I didn’t really have to change much of my mindset. It was just more dealing with Kerry and being more in touch with him as opposed to getting information through Jared every day.

This promotion did put your “shipuationship” with Sunny in a bit of jeopardy. How did you navigate the new dynamic together?

I think navigating it is probably the key word there. It was very difficult having to step up and be her boss rather than an equal. That was the hardest thing for me. At the end of the day, I came into the season wanting to get that promotion and be a bosun on the biggest boat in Below Deck history. I wanted to be the first Australian Indigenous person in Australian history to take on a head of department role on a platform like this. That was my focus.

The relationship side of things was very much on the back burner for me. It was very hard to explain that to her because she didn’t understand the position I was in. So, it was hard. Sunny and I went back and forth a lot while we figured things out. Katie [Glaser] and Ross did it last year, and it didn’t work out.

We also had stew Cat Baugh leave the St. David this episode. Were you surprised to see her go?

Talk about a double whammy. I was surprised to see Cat go. I didn’t know the extent of her interior struggles because she seemed all right on the outside. I got only little glimpses of her turmoil and what I would hear from Fraser and Barbie and the other people. Xandi [Oliver] is obviously very strong, but Cat, she just couldn’t hold her own. She was very much a small yacht stewardess, very California vibes. She was very laid back and that’s why she was having so much trouble. The super yacht industry is very much sink or swim, and she sank unfortunately. Two people off in the one episode. Can you believe that?

And we’re not even halfway through the season.

What could go wrong?

As she was leaving the yacht, you comforted Kyle by saying, “That’s the way it goes. That’s yachting, mate.” Is it a common occurrence in the yachting industry to have crew shifts like?

It’s not. It was also very unexpected the way she left because we were still underway. We dropped the anchor, and she got off the yacht. Normally, you’d probably wait until you get to the dock or whatnot. I think Cat was very much at her wit’s end. She needed to get off and deal with what she had going on. I don’t blame her. The yachting industry does take a very big mental toll on everyone. If people say that it doesn’t, then they’re lying or being dishonest.

On the trailer for next week, we get a glimpse of the new deckhand’s arrival. What can you tell us about Dylan?

Mr. Dylan [laughs]. He’s a very good-looking fellow, to say the least. All the girls were very much peacocking around him. Though, I think it’s always good to have what we call “fresh meat” in the industry come on board. Dylan is that. People love to get into relationships on board, so the single people are always looking for the next person to come along. Dylan’s fantastic. We went over his CV, both Kerry and I. When we got word that he was joining the crew, we felt like it was a breath of fresh air. His CV was very impressive. He’s definitely a contender for the lead deckhand role now that I’m not in there anymore.

When Bravo.com asked you to describe this season in three words, you wrote, “Almost broke me.” Can you elaborate on that?

“Almost broke me.” [laughs] I think I’ve never dealt with so many frictions between people and departments. Stepping up into the bosun role was challenging, at times. I’m very much a people person, but I had to have hard conversations that very much didn’t go in my favor a lot of the time. I felt a lot of friction with Kerry and Fraser specifically. I dare say that we’re not that close any more because of the season.