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Rb Hip Hop

Drake Surprises Pregnant Fan With VIP Upgrade and Cash Giveaway at Sydney Show

"Are you 20 weeks pregnant? Get out of the pit. Get outta there," Drake told the fan.

Drake
Drake
Norman Wong

Drake’s Anita Max Win Tour in Australia continues to deliver viral moments—this time, with the rapper handing out $30,000 to a pregnant fan at his Sydney show at Qudos Bank Arena on Wednesday night (Feb. 19).

During a break in his set, Drake was scanning the crowd for signs when he spotted one that read: “I’m 20 weeks pregnant.” In a video circulating social media, the “Hotline Bling” rapper immediately reacted with disbelief.


“Are you 20 weeks pregnant? Get out of the pit. Get outta there,” Drake told the fan, later identified as Tiana Henderson, before instructing security to move her to VIP seating. “Give her some VIP tickets immediately and like $30,000,” he added before jokingly asking, “Who the f—brings a baby to a mosh pit?”

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Henderson and her friend were then escorted out of the packed general admission area to a more comfortable spot in VIP.

Drake’s latest giveaway is just one of many on his Anita Max Win Tour, where he has been handing out cash to fans throughout Australia. At his Melbourne show earlier this month, he reportedly gifted a fan $25,000 after noticing a sign referencing his son, Adonis, and another $20,000 to a concertgoer celebrating her birthday. While performing in Perth, he handed out $40,000 to two fans, including one waving the Canadian flag.

Earlier this week, he made headlines again by giving $30,000 to a fan in Sydney who held up a sign asking for help to quit their job at McDonald’s. The rapper played into the Australian slang, repeating the request in an exaggerated Aussie accent: “Help us quit Maccas, mate.”

In addition to his on-stage giveaways, Drake has been using the tour to promote $ome $exy $ongs 4 U, his newly released joint album with longtime collaborator PARTYNEXTDOOR, who has joined him on-stage during his Australian tour.

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Released on Feb. 14, the project has been a commercial success, earning over 56.6 million first-day streams on Spotify—making it the second-highest debut of the year. $ome $exy $ongs 4 U also broke the record for the biggest R&B/Soul album in Apple Music’s history by first-day streams worldwide.

Drake and Party are set to headline the first day of this year’s Wireless Festival in London with special guest Summer Walker in July. Drake will also headline the next two days with “The Mandem,” Burna Boy, and the Worl’ Boss Vybz Kartel by his side.

This article first appeared on Billboard U.S.

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Connor Storrie and Hudson Williams attend the premiere of "Heated Rivalry" at TIFF Lightbox on November 24, 2025 in Toronto, Ontario.
Harold Feng/Getty Images

Connor Storrie and Hudson Williams attend the premiere of "Heated Rivalry" at TIFF Lightbox on November 24, 2025 in Toronto, Ontario.

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‘Heated Rivalry’ Is Getting an Official Soundtrack — and It’s Coming Sooner Than You Think

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Heated Rivalry, the wildly popular queer hockey drama starring Connor Storrie and Hudson Williams, has taken the world by storm since its premiere in November. The Jacob Tierney-helmed Crave original (which airs on HBO Max in the States) has garnered hundreds of thousands of fans who have fallen in love with the show’s synchs and score, and they’ll soon be able to stream its official soundtrack, Billboard can exclusively confirm.

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