All the awkward videos of Lily Phillips going on a date with Drake, and what’s actually going on

In the last few days, a whole bunch of videos have emerged of Lily Phillips going on a date with Drake. It’s all a bit toe-curling, and now I’ve seen it, I can’t take that time back.

Videos have been spreading across TikTok and Twitter, of Lily going on a date with Drake, as part of his stream. He also took a whole bunch of other women and OnlyFans creators on dates.

It’s all part of a stream he hosted on Kick. Drake has been trading in music for online streaming, and teamed up with a gambling brand to post a bunch of videos. The stream was around three hours in total, and it saw Drake go on quick-fire dates with 20 women.

One of which date Drake had, was with Lily Phillips. Within minutes, there were viral clippings of their awkward encounter absolutely everywhere.

Drake meets Lily Phillips during his 20 vs 1 Dating Show on stream 💀 pic.twitter.com/keX5TR4Erm

— DrakeAligned (@DrakeAligned) August 9, 2026

“My name is Lily Phillips, otherwise known as a super sl*t,” Lily announced, as she walked into the room for the date. “Today, I’m rebranding as Drake’s wife.” Drake then complimented Lily’s tan, to which she very oddly replied that she was “trying to get to your colour”. Welp.

“I don’t know if we’re allowed to say that,” Drake replied, clearly a bit taken back. Lily was then asked to explain her “official job title” beyond “super sl*t” and said she is “known as an OnlyFans girl”. It was all a bit more awkward, as clearly Drake didn’t understand much of what she was saying.

@blondechallengegi

Drake is lowkey falling in love with Lily Phillips 😭 #lilyphillips #drake

♬ original sound – blondechallengegirl

After the first introduction, the pair then went on a 1-1 date. They sat at a table, presented like a romantic dinner date, with roses all over it. Lily seemingly didn’t like Drake not wanting to know more about her childhood, and instead pushing for a “normal conversation”.

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So, things quickly went materialistic, and she asked him if he had a pool at home. “I do. I have two,” he replied. He then explained it was one indoor, one outdoor. “I’d love to play in it some time,” Lily replied. Drake then called Lily “really sweet” but she was already getting up and walking out. Ouch.

“I was going to give you a snog for some reason,” she said, walking out. I can’t lie, I’m getting quite mixed messages here. Drake then called her “Liler” which is…. cute?

Drake with Lena The Plug & Lily Phillips 👀📸 pic.twitter.com/b16vcruiSv

— DailyRapFacts (@DailyRapFacts) August 9, 2026

It would seem they got along alright though, as pictures have emerged of Lily and Drake hanging out with fellow creator Lena The Plug, who was also on the stream. And there’s a video of them after filming, doing shots in a club together.

Drake was seen chilling and taking shots with Lily Philips after his 20v1 stream 😭 pic.twitter.com/ViYECSMnMz

— ryan 🤿 (@scubaryan_) August 9, 2026

But this apparently wasn’t their first link up. Anything but, actually. Lily has previously spoken out about dating Drake.

They apparently had a bit of thing last year, after they met through mutual friends. They are said to have exchanged DMs, before hooking up when he was in the UK for a concert. He apparently wined and dined her by hiring out an entire restaurant for them.

This is said to have all fizzled out, when Drake found out about Lily’s viral stunts. Brutal. It was all very lowkey, and they just put the whole thing to bed. Now, Lily has an official boyfriend anyway.

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