A Pageant Princess, Actors & A Guy Who Won’t Date Someone With A “Swag Gap”: Meet The Cast Of Mediacorp Dating Show Wingman
Eight singles from around the region enter a villa with their best friends playing cupid. Here’s who you’ll be watching — and stalking on Instagram.
Would you trust your best friend with your love life?
On Mediacorp's new regional reality dating show Wingman, which premiered on Sep 10, eight singles do exactly that.
Think dating show in a villa, except the eight sexy singles aren't navigating the romantic minefield alone.
Each has brought along a best friend — aka their wingman — who has to tackle challenges to earn them dates, size up potential matches and, hopefully, stop their pal from making terrible romantic decisions.
Hosted by 987 radio jock Germaine Tan, the 12-episode series features contestants based in Singapore, Thailand and the Philippines.
And it's quite the cast.
There’s a pageant princess, a Thai actress fresh out of a seven-year relationship, and a former SEA Games wakeboarder who's prepared to use gymnastics or dance to get a woman's attention.
Oh, and their wingmen include a palm reader, psychology undergrad and film stuntman.
The winning couple walks away with S$20K, while the winning wingman gets S$10K.
Meet the singles and their wingmen:
Cheryl, 24 (Singapore) | Instagram
Pageant princess Cheryl — she was second-runner-up at Miss Petite Global Singapore 2025 — was raised “like a princess” by her dad and would like to be treated like one.
She works in social media marketing for her parents' business and wants a romantic guy who'll make her feel special. A Ferrari would be welcome, she jokes, and slippers are okay — as long as they're Versace.
Her Wingman: Krystal, 30 (Singapore) | Instagram
Healthcare services professional Krystal is a fellow pageant girl and was crowned Miss Global Asian Singapore 2026. She also reads palms and reckons she can spot red flags quickly — very useful on a dating show, we'd say.
She's looking out for a kind-hearted guy for Cheryl, though the besties joke that a healthy bank account wouldn't hurt.
His Wingman: Josh, 28 (Singapore) | Instagram | TikTok
Former child actor and content creator Josh — you may have spotted him in KFC's BBQ Cheeseburger ad — shares Tyler's love of fashion but is the more measured one of the pair.
His job, essentially? Stop his impulsive bestie from creating more romantic drama.
Frayya, 23 (Thailand) | Instagram | TikTok
Thai actress Frayya, whom you might remember from 2024 series A Love So Beautiful, comes from an entertainment family — her mum is an actress too. She joins Wingman after a seven-year relationship that didn't have her family's approval.
Despite being used to getting attention, she admits flirting doesn't come naturally to her. Age and looks aren't deal-breakers either.
Sam, 29 (Singapore) | Instagram
Where do we even begin with Sam's résumé?
He's a gymnastics coach, voice instructor, theme-park performer and former SEA Games wakeboarder.
After three long-term relationships, he's looking for a sporty Asian partner who's a “10 out of 10” — and is prepared to use gymnastics or dance to impress her. One thing he won't do for love? Shave off his signature moustache.
His Wingman: Hadri, 31 (Singapore) | Instagram
Freelance film stuntman Hadri is also an occasional B-boy and K-pop dancer. Despite having been on plenty of first dates, he's never actually been in a relationship.
Does that make him the best or worst person to give dating advice? We'll find out.
Olivia, 29 (Singapore) | Instagram | TikTok
Financial auditor and hopeless romantic Olivia has been single since 2019 and wants someone who'll be open about their relationship after an ex kept theirs a secret.
Her ideal man? Active, clean-cut, preferably with a PhD and Korean-inspired looks. Facial hair need not apply.
Her Wingman: Yuki, 25 (Singapore) | Instagram | TikTok
Marketing director Yuki is Olivia's K-pop dance buddy and the tougher one of the pair.
Having survived a difficult relationship herself, she reckons she knows what trouble looks like and isn't afraid to grill Olivia's potential matches for red flags.
Gigi, 33 (Thailand) | Instagram
Originally from Canada and now based in Thailand, Gigi leads technology for a hospitality group.
After eight years with a partner she felt wasn't living up to his potential, she wants someone driven, intelligent and kind — or, in her words, “a Hyrox man with brains and a heart”.
Her Wingman: Radhika, 33 (Singapore) | Instagram
Singapore-based technical trainer Radhika grew up on enough Bollywood to have pretty cinematic expectations of romance. Real-life dating, however, hasn't quite lived up to the movies.
She reckons she knows not just what Gigi wants, but what she actually needs.
His Wingman: Richard, 33 (Philippines) | Instagram | TikTok
Model, actor and media entrepreneur Richard is a self-described hustler and natural networker.
He plans to read the room and help L.A make the most of every opportunity. Basically, networking — but make it dating.
Wingman is available on mewatch and the Mediacorp Entertainment YouTube channel, with two new episodes released every Thursday until the finale on Oct 8.
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