My special Valentine!! They say dating a rockstar is hard, but YUNGBLUD made it very easy!

On this episode, YUNGBLUD chats with Tait McGregor about his ideas of love, his parents' relationship, how love has informed his art, falling in love as a rockstar, and more.

YUNGBLUD rose to prominence for blending pop-punk, alternative rock, and hip-hop with outspoken, youth-driven lyrics about identity, mental health, and political frustration. He broke through globally with high-energy anthems like I Think I'm OKAY (with Machine Gun Kelly and Travis Barker), Parents, and 11 Minutes featuring Halsey. Known for his chaotic live shows and strong connection to his fan community, he has since cemented his mainstream status with hits such as Fleabag and Tissues.

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!

Jessie Murph goes on a Date With Tait!

In this episode, Jessie Murph shows Tait McGregor some Southern hospitality, teaching her about the Thanksgiving delicacy of okra, about her 'Dirty Mind Quizzes', how she freestyles her lyrics, how Drake was in her DMs, her dream collab and getting over the cringe.

Jessie Murph is a breakthrough American singer-songwriter who rose to fame through TikTok and YouTube, where her emotionally charged vocals and confessional lyrics quickly went viral.

She’s known for major hits like “Pray”, “I'm Not There For You”, “Blue Strips”, “Forever” (with 6LACK), “Wild Ones” (with Jelly Roll), and “Heartbroken” (with Diplo & Polo G), which have driven her rapid rise in the pop and alt-pop scenes.

Her latest album, Sex Hysteria, showcases her signature blend of pop, country, and dark alt-pop, cementing her status as one of today’s most searched and talked-about new artists.

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

Del Water Gap goes on a Date With Tait!

In this episode, Del Water Gap and Tait McGregor deep dive into the psyche, learn about Del Water Gap's relationship with his 102-year-old grandma, their thoughts on the concept of dying, the intricacies of dating and more.

Del Water Gap is the indie-pop solo project of American singer-songwriter and producer S. Holden Jaffe, originally from Connecticut and now based in Brooklyn, New York.

He first gained widespread attention with his 2020 single 'Ode to a Conversation Stuck in Your Throat', which helped establish his reputation for emotionally intimate songwriting and dreamy, atmospheric pop production.

Since then, he has released full-length albums and built a dedicated following through his evocative sound and collaborations with other artists. He's currently gearing up to release his studio album 'Chasing the Chimera'.

A big thank you to ATTENZIONE! Food & Wine for hosting our first date!

Allday goes on a Date With Tait!

On this episode, Allday and Tait McGregor discuss his parent's divorce, his brief stint as an olive picker in Italy, his dating history, siblings, Allday's love of Step Up and Clairo, and his battle with ALLDAY PROJECT.

Tom “Allday” Gaynor is an Australian rapper, singer and songwriter from Adelaide who first made waves in 2011 by uploading tracks online for free. After a move to Melbourne and a signing with Illy’s ONETWO label, his debut album Startup Cult (2014) reached No. 3 on the ARIA charts, establishing him as a rising force in alternative hip-hop. Over time, Allday’s sound has evolved—blending rap, indie-pop, dream pop, and rock influences—and his later albums reflect a more melodic, introspective style. He's collaborated with the likes of Troye Sivan, Mallrat, Cub Sport and YNG Martyr; and is well known for his hits including 'Always Know The DJ', 'Girl In The Sun' and 'In Motion'.

Medium Build goes on a Date With Tait!

On this episode, Medium Build opens up about kids and fertility, his biological dad, dating culture, his album 'Country', social media detoxing and how he got his iconic gold tooth.

Medium Build, aka Nick Carpenter, is an American singer-songwriter whose music blends indie-folk, country, and bedroom-pop with emotionally candid lyrics and a deeply authentic voice. Hailing from Atlanta, Georgia, he’s built a devoted following through intimate performances, heartfelt storytelling, and standout support slots for artists like ROLE MODEL, Alex Warren and Lewis Capaldi. In 2023 he signed with Slowplay/Island Records and in 2024 released his fifth studio album, Country, marking his major-label debut and earning wider recognition in the indie music scene. He's just released his new single 'Last Time' - the first foray into a new chapter for Medium Build.