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The Daily Dish Winter House

Malia White's Relationships As Seen on Winter House and Below Deck Mediterranean

The yachtie had a few memorable boatmances before joining a new cast in Steamboat Springs.

By Sophie Vilensky

Since joining the Bravoverse in 2016 as a deckhand on Below Deck Mediterranean Season 2, Malia White has established herself as a favorite across franchises. While fans love the yachtie for her strong work ethic and adventure-seeking outlook, it's also fun to keep tabs on her romantic life —of which we've seen a lot. And when Winter House Season 3 premieres on October 24, we may see even more:  As Malia notes in Episode 1, she's currently single.

How to Watch

Watch Winter House on Peacock and the Bravo app.

“After a long-term relationship and seven-month dry spell, yachtie Malia White is looking for some action off the water and is ready to showcase her old stomping grounds of Colorado to the rest of the group," the show's press release reads.

But before we can look to the future, there's history to revisit. Over the years, Malia has had several boatmances, some ending better than others. Keep scrolling to look back at her relationship history both on and off deck.

Malia White and Wes Walton

When: Season 2 of Below Deck Mediterranean

Malia White Wes Walton Friends

When Malia joined Season 2 of Below Deck Med, she found herself caught in a love triangle with bosun Wesley Walton and chef Adam Glick. In the end, Malia chose Wes and the two continued their relationship after the charter season ended.

While their love didn't end up lasting forever, Malia revealed in a June 2020 interview with Bravo Insider that she's still friends with Walton.

"He has had some amazing yachting experiences recently. He’s been traveling all over the world," Malia said of Wes. "We’re still good friends. He keeps me updated with his travels, and I tell him about mine."

Malia White and Chef Adam Glick

When: Season 2 of Below Deck Mediterranean

Adam Glick Below Deck Sailing

During Season 2 of BDM, Malia engaged in some flirting with the "adventure chef" Adam Glick. (Eventually, it was revealed that the pair had connected before they had even boarded the Sirocco.) When Wes entered the picture, things came to a head and Malia chose the bosun.

"Sometimes a girl just can't make up her mind..." Malia wrote in an Instagram post referencing the love triangle in June 2017. "Note: I know I made mistakes playing with [hearts] forgive me — I'm only human."

While the pair aren't in contact anymore, Malia wishes Adam nothing but the best.

“I have no hard feelings towards Adam," Malia told The Daily Dish in June 2020. "I think there’s definitely a good guy in there somewhere. We just don’t keep in touch."

Malia White and Tom Checketts

When: Season 5 of Below Deck Mediterranean

Tom Checketts Malia White Split

During Season 5 of Below Deck Mediterranean, fans got to see Malia's relationship up close when her boyfriend of about a year, Tom Checketts, took over chef duties in Season 5 Episode 11. He joined the team at the request of Captain Sandy Yawn after the previous chef, Hindrigo "Kiko" Lorran, was let go.

"Tom coming on board as chef was like a nightmare. On a selfish level, I wanted this to be about me becoming bosun, and I think Tom coming on board, it's now Malia and Tom. We're like a team," Malia shared during Season 5, Episode 13 of the Below Deck Mediterranean After Show. "That's a whole 'nother dynamic you have to worry about."

After a long distance romance, Malia announced their breakup in September 2020. “Yes, Tom and I have split. The details surrounding all of it I am trying to keep a little private just out of respect to him and I,” she said via an Instagram video. “But yes, I am single.”

Later, the pair noted their long-distance situation led to the demise of their relationship.

"I don't want people to think this is yachting and this happens all the time," Malia shared during a Watch What Happens Live with Andy Cohen appearance the same month. "It's just distance, and it's sh-t, but I'm focused on my career."

Malia White and Jake Baker

When: Post-Below Deck Mediterranean Season 6

Malia White Dating Engeneer Jake 01

Malia and Jake Baker's romance was confirmed in August 2021, when Jake posted a photo of the pair kissing. Malia met the hunky engineer during Season 6 of BDM (he only made a brief appearance on TV, but was there nonetheless).

In February 2023, she announced that they'd called it quits after two-plus years together.

"So obviously I’m single,” Malia told Showbiz CheatSheet, going on to discuss how her last two relationships were founded at work. “Jake and I met on the same boat. Tom and I met on the same boat ... I went from such a really intense relationship with Tom, like straight into a relationship with Jake. And I never had time to kind of take a break.”

RELATED: Malia White Opens Up About Her Split from Boyfriend Jake Baker — and What’s Next for Her Dating Life

While Malia will never say never when it comes to workplace romance, her next relationship will be thoughtful.

“I’m not going to say I’ll never date a yachtie again, but I’m definitely going to choose wisely,” she added. 

Malia White and Katie Flood

When: Never

Malia White and Katie Flood smiling while enjoying their time in Monaco.

When a fan asked Katie Flood if she and Malia were dating during a May 2023 Instagram Q&A, the BDM Season 6 chief stew couldn't help but giggle.

RELATED: Katie Flood and Malia White Explain their Relationship Following Their Below Deck Med Days

No," Katie wrote, adding a laughing-crying emoji. "We are best friends that work and live together and have a lot of other amazing opportunities that we get to do together. We are so [lucky] to have each other and get to work towards our goals, dreams and our futures side by side of each other. She's my work wifey for life."

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