Gabby Windey Wants The Love Overboard Contestants To “F*cking Chill”

Ever since she entered the Bachelor Mansion as a contestant in 2022, Gabby Windey has been an undisputed reality TV icon. Now 35, she has only solidified that status with stints on The Bachelorette, Dancing with the Stars, and The Traitors. But it wasn’t until May 2025 that the Los Angeles-based podcaster was finally tapped to step into the role of host. Love Overboard, a surprisingly competitive dating reality show produced by Alex Cooper’s Unwell Network, brought Windey aboard for its inaugural season on the high seas. The first season is streaming now on Hulu.

“The competition aspect is kind of like Love Island meets Traitors,” Windey told Bustle during a June 2025 visit to the set. The show also has a touch of Below Deck to boot.

Love Overboard features 22 singles who hope to find love aboard the Chakra, a 280-foot superyacht, sailing around Malta. But the show isn’t all surf and sun. Once contestants couple up, they get to enjoy the boat’s luxury amenities on the Topside. Single contestants get demoted to the Downside, where they spend their days doing chores. The only way to change their fate is to invite a Topsider on a date and win them over. Failure means getting planked, losing out on the chance to find love at sea and take home the grand prize for the last couple standing: a free trip around the world.

Windey is the ship’s Love Captain, offering commentary on the latest drama and moderating the splashy planking ceremonies. “I’m just trying to hype up the girls as much as I can,” she says. “Dating in the real world, we know how often women fall victim to f*ckboys. I want to remind them, ‘Girl, you're so hot. Act like it. Make them work for it.’”

I caught up with Windey in her dressing room, as her hair and makeup team applied the finishing touches ahead of that night’s planking ceremony. “We start glam three and a half hours before I come to the boat. It’s not easy being a woman. I have to have a personality, and I have to wear pasties on my nipples,” she says.

In her final minutes before filming, she often gets a “debrief” from the ship’s crew and puts on her go-to playlist. “We've been listening to Chappell Roan to keep the gay vibes going because it seems so straight around here,” she says. “The contestants are very heterosexual. Give them a couple years, you know? They’ll come to my side.” (In 2023, Windey began dating a woman, Robby Hoffman, whom she married in January 2025.)

She has a McDonald’s bag on the vanity in front of her, but when her makeup artist asks if she wants “one chicken nug, just for luck,” she opts out. Her white dress is a rental, and she can’t risk any stains. Plus, she’s eager to get this show on the road. “Let me get these couples overboard and get the f*ck out of here so we can get a sweet and sour,” she says.

Below, Windey discusses yacht life, her approach to hosting, and more.

It’s a maze inside the ship. Do you feel like you know your way around now?

Not at all. I’m babysat everywhere, so I actually don’t have to think that much. There are all [these] railings that you can fall off [of]. I also have tinnitus, so my inner ears are already f*cked up, so I do great [on a boat].

Do you ever give advice to the contestants, or do you try to stay unbiased?

I have favorites. I can't help it. I'm very opinionated. I'm like, “Are you sure you want to go with this guy?” I want to guide them, like, “Girl, [pick] this one.”

But to them, I try to be very objective and keep my expressions under wraps, [though] I don't know if it's ever working.

How have the contestants changed as the show has progressed?

I just watched them in the control room. Today they were giving messy b*tch. Some sh*t went down. [The contestants are] getting crazier, surprisingly. I'm like, “F*cking chill.”

A lot of them came on the show to escape the typical dating scene. Why do you think dating is so tough right now?

Men don't have to work for anything anymore, and they've gotten used to it, and now women are demanding to be treated right. We have careers and education. Some of the men just don't like it. They get intimidated.

How has your relationship with Robby changed your perspective on love and influenced your approach to hosting this show?

I'd probably be just so jaded [if I hadn’t met her]. I had been through so many experiences [with dating], and they all failed. Don't get me wrong, I’m still jaded, but I'm lucky to be in love. It's made me softer.

How do you deal with being in the public eye?

I'll get one bad DM, and I'll spiral for days. But then I’ll remember what Cardi B said: Haters means you made it. It’s true. At this point, I don't want everyone to agree with me and understand me, because I'm not for everybody. That would mean I’m adjusting myself to a mold that I don't want to be in.

What has been your favorite part of filming?

The planking. It’s so sick and kind of primal. They all show up in their best outfits — if it were me, I would ask for a wetsuit.

It is terrifying because you don't know what's in the sea. Much of it has yet to be discovered, just like space. We're so worried about going to Mars, but like what the f*ck [is in the water] around Malta? Nobody knows.

This interview has been edited and condensed for clarity.