Guys, we’ve just learned how Drake and Lily Phillips’ relationship came crashing down after he’d booked out an entire Italian resturant to “wine and dine” her.
Their brief fling actually happened in 2025, after they met through mutual friends, but we only learned about it now after sources came forward.
“He was asking her lots of questions about herself and really showed an interest in her. He’s a global megastar, so Lily was quite taken aback and she couldn’t believe how nice he was. He really wanted to make sure she had a great time,” they told The Sun last week.
After exchanging some flirty DMs, Drake hooked the OnlyFans girly up with a private VIP booth at his July 2025 Birmingham show.
“After the gig, he surprised her by hiring out an entire Italian restaurant so he could wine and dine her. He went all out to impress her and it was really romantic,” the source added. “They went back to his hotel to continue the party, and have continued texting each other since.”
We were left wondering whether they’re still in contact, but now new sources have detailed the brutal reason Drake broke up with Lily Phillips.
Apparently, Drake wasn’t aware of Lily Phillips’ stunts
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According to fresh sources who spoke to Radar Online, Drake was very keen “on making sure she enjoyed herself and felt looked after.”
“At the beginning he appeared genuinely taken with her, paying close attention and acting like someone who was clearly infatuated,” they said.
But this love story was not written in the stars, and apparently, Drake was unaware of the sheer lengths Lily had gone to on her quest for OnlyFans supremacy. Sure. Totally believable.
The source explained: “As he became more aware of the content Lily had put out online, especially some of the more extreme and provocative stunts, he grew increasingly uneasy. He was genuinely repelled by parts of it and felt it clashed with his own values, his public image and the sort of lifestyle he wants for himself.”
Another source claimed that Drake is – and try not to laugh at this one – “conscious of his image and the principles he lives by.” Yes, the same Drake who was accused of getting fake abs and buying his music listening numbers.
“It felt wrong to him, even exploitative, and he realised he could not square that with the idea of building anything serious or lasting with her,” the source added.
They said the breakup was very lowkey
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Though drama seems to follow Drake across the globe, the breakup with Lily Phillips was apparently quite chill.
“There was no big argument or showdown. He simply came to the conclusion that they were heading in completely different directions, both in their personal lives and professionally,” the source explained. “After seeing the more extreme elements of her content, he knew it was not something he could endorse or be linked to in the long run.”
Apparently, Lily was less upset about the breakup itself and more upset about being judged for her profession.
“She is fiercely independent and unapologetic about that, so it is upsetting to see her judged or dismissed because of the career she has chosen,” one of her friends told the publication.
We almost had something great. Almost.
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Featured image credit: Lily Phillips/Drake
