Thomas Day goes on a Date With Tait!

In this episode, Thomas Day tells Tait McGregor all about his family back in Nashville, his love of candles and scents, his pride in his hygiene, his love of Aussie beaches and his tooth gem.

Thomas Day is an American singer-songwriter who gained early attention through The Voice and viral online performances. He’s best known for his breakout hit “She’s Got A Thing About Her,” which became his most streamed and widely recognised song and helped establish his emotionally raw, Gen Z–focused pop sound. Other notable tracks include “Not My Job Anymore” and “Love Me for Another Day”.

A big thank you to Chuck Trailers for hosting our first date!

DISCLAIMER: This was filmed in December 2025, prior to the Shark Beach attack in Sydney, where there have been no other prior recorded shark sightings.

Jeremy Zucker goes on a Date With Tait!

In this episode, Jeremy Zucker becomes Tait McGregor's dating guru. He shares wisdom about falling in love, how he knew his wife was the one, the intimate details of their love story, his feelings about becoming a dad and what went down at his bar mitzvah.

Jeremy Zucker is an American singer-songwriter and producer who first gained fame for his emotionally honest indie-pop and bedroom pop-influenced music, with breakout hits like “Comethru”, “All the Kids Are Depressed”, and the duet “You Were Good to Me” with Chelsea Cutler.

He’s known for blending introspective lyrics with catchy melodies and has released several albums including Love Is Not Dying (2020), Crusher (2021), and most recently Garden State (2025), supported by singles like “hometown” and “surprise!” that reflect on his roots and personal growth.

In the past year he’s been promoting Garden State with new music and an international Welcome to the Garden State Tour, reconnecting with fans and exploring themes of nostalgia and maturity.

A big thank you to Tio's Cerveceria for hosting our first date!

Holly Humberstone goes on a Date With Tait!

In this episode, Holly Humberstone tells Tait McGregor about her childhood and sisters, rediscovering old relics, exploring the next chapter for her artistry, her relationship with London and travel, and being in her lover-girl era.

Holly Humberstone is a British singer-songwriter celebrated for her emotionally candid indie-pop and alternative music, who broke out with early hits like “Falling Asleep at the Wheel,” “Deep End,” “Haunted House,” and “Scarlett.”

In 2022, she wont the Brit Award for Rising Star before releasing her debut album Paint My Bedroom Black in 2023.

She followed up with the Work In Progress EP in 2024, which includes newer tracks like “Dive,” “Work In Progress,” “Down Swinging,” and “Easy Tiger.”

Most recently in 2025 she’s put out fresh singles such as “Die Happy” and “Sleep Tight,” further expanding her profile as a defining voice of her generation.

A big thank you to El Primo Sanchez for hosting our first date!