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Love Island USA Star Kassy Reveals What Grand Gesture Made Her Take Leo Back

Leo made a big mistake in his relationship with Kassy on Love Island USA Season 5.

By Tyler McCarthy
Kassandra Castillo and Leonardo Dionicio pose for a photo together before their one on one date

Although they were only the runners-up in Season 5 of Love Island USA, there’s no doubt that the many ups and downs of Leo and Kassy’s relationship made for the most interesting and intense moments this summer. We all know they eventually ended up together, but Kassy recently revealed to USA Insider what exactly won her back to Leo after his many mistakes. 

How did Leo win Kassy back?

After Casa Amor, Leo and Kassy’s seemingly unbreakable bond was not only broken, but she declared that there was absolutely no way it could ever be repaired. Undeterred and spurred on by his intense romantic feelings for her, Leo began a campaign in the villa aided by his fellow Islanders to win Kassy back through grand romantic gestures like writing love notes on her mirror, setting up elaborate dates, and pulling her aside for chats as often as possible to overcome her being “disgusted” by his actions. 

Ultimately, it worked and the duo recoupled and lived happily ever after. Despite their clear love story, many were puzzled by Kassy’s decision to take Leo back after what he did. Speaking to USA Insider, she finally explained which of his many grand gestures of love ultimately made her decide to give him a second chance. 

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“I think the one that worked best was him saying, ‘I love you,’” she revealed. “He didn’t have to say that. It also just seemed that, even after his gestures, he was still pouring his heart out, knowing I told him the door was closed romantically, knowing that he saw me pursuing other people, having different conversations, and he still grabbed me, he still made the effort to open up his heart.” 

In the end, for Kassy, it was not about any big romantic gesture on Leo’s part but a persistent demonstration of his true feelings for her despite his big mistake during Casa Amor. 

Kassandra Castillo and Leonardo Dionicio hold hands during their one on one date.

“He put himself in such a vulnerable position,” she continued. “Even telling me he loves me was a big shock, but also that was the moment I realized he really means what he’s doing. Doing these gestures, they’re nice and all, but what else? What else is the reason for all this? So, him saying that was like… I think it was the most vulnerable position to be in and I was really happy that he did that.”

She concluded: “You stand by what you said and your actions, I think he’s doing just that. So, I’m proud of him.”

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What happened between Leo and Kassy?

For those who need a refresher on the storied history of Kassy and Leo, they coupled up immediately. He was briefly stolen by another single but it didn’t take. It seemed like nothing could break his attraction to Kassy — until Casa Amor. Like many Love Islanders before him, Leo quickly succumbed to the temptation of a new bombshell in the villa while his partner was away. 

Kassandra Castillo and Leonardo Dionicio pose for a photo together during the Love Island Season 5 finale.

Kassy came back to the villa with a new man, Matia, thinking she was about to break Leo’s heart only to discover he’d had sex with Johnnie while she was gone. Kassy would go on to more than mend fences with Johnnie, but Leo was another story. Unlike other couples in the villa whose relationship was basically smooth sailing from moment one, Kassy and Leo used their time on the island to put their relationship through tests that would otherwise break two people with a worse connection. Now that it’s all over and done with, they’re both looking toward the future. 

“Give me some time to adjust to this whole thing and then, a few years from now, I’m gonna look back and be like, ‘Aw, my 20s,’ you know?”

Catch up on Love Island USA only on Peacock.

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