Stingray’s new Hawaii and wedding clues send ‘The Masked Singer’ viewers chasing a new theory

Tropical visuals, a mystery proposal, and music royalty hints push Stingray to the center of ‘The Masked Singer’ Season 14 buzz.
A still of Stingray while performing on 'The Masked Singer' Season 14 (Cover Image Source: Instagram | @maskedsingerfox)
A still of Stingray while performing on 'The Masked Singer' Season 14 (Cover Image Source: Instagram | @maskedsingerfox)

With the new season of ‘The Masked Singer’ officially in motion, viewers are once again squinting at props, replaying clue packages frame by frame, and bickering in the comments. And right now, all eyes are on Stingray. The aquatic character glided back onto the stage during the February 11 episode, swapping out earlier disco sparkle for something more current. This time, Stingray performed ‘Bad Habits’ by Ed Sheeran. The vocals were smooth and confident. He didn’t sound like a rookie. However, the topic that got fans really excited, though, was the clue package. Because this week, romance was front and center, and so was Hawaii.

The visuals started with a beach house with a tropical background. Palm trees were swaying back and forth. Ocean breeze types of vibes. Then came a fish tank with a basketball floating inside, which was random but also very not random if you’re playing along at home. Stingray shared that after years of “running around,” the love of his life “came dancing” into his world. There was champagne. A sparkling diamond ring. A witch hat that looked suspiciously like it had been borrowed from Hogwarts. A cat. A note that read, “Call exterminator.” And an empty ring box paired with a ringing phone. That’s not subtle.

The Hawaii imagery mixed with the basketball clue sent the panel spinning in new directions. Jenny McCarthy Wahlberg immediately tied the basketball to ‘High School Musical: The Musical: The Series’ and tossed out Jordan Fisher as her guess. She pointed to his theater background and crisp vocals. Ken Jeong floated Joey McIntyre, citing his Broadway stint in ‘Wicked’ and his long-standing marriage. That suggestion was quickly shut down, though. Jenny wasn’t buying it. “He doesn’t sound like that at all!” she shot back. Meanwhile, Rita Ora noticed the cat and witch hat clue and briefly entertained the idea of a connection to Cat Witch.

But, she ultimately wrote down Jason Derulo as her final answer. Meanwhile, earlier hints this season pointed to Hollywood roots, with references to Sunset Boulevard, the Chateau Marmont, and a mother who hosted icons like Marvin Gaye, Luther Vandross, and Stevie Wonder. Names like Jaden Smith, Lil Romeo, Patrick Schwarzenegger, and Donald Glover have all floated around as the panel's guesses. Now, media outlet Just Jared has come up with its own theory: Evan Ross. And honestly? The puzzle pieces kind of click. In one of the clue packages, Stingray mentioned being a regular presence on Sunset Boulevard. Evan once owned a home right on the Sunset Strip. 

Then there’s the family angle. Evan is the son of Diana Ross, whose legendary parties were known to attract music heavyweights for decades. The earlier clue about a mother hosting Gaye, Vandross, and Wonder? That lines up. There’s more. Evan is married to fellow singer Ashlee Simpson, which fits perfectly with the romance-heavy theme this week. Engagement rings, champagne, tropical settings. And here’s a fun part: Evan’s ex-girlfriend Aubrey O'Day previously competed on the show as Ant in Season 13. That’s not exactly proof, but it’s an interesting coincidence. Still, nothing is locked in. 

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