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Drake unexpectedly had an encounter with adult film star Lily Phillips at a 20 v 1 'date.'
The superstar rapper, who recently released three albums at once, hosted a livestream with Stake and Kick with a very eye-catching premise.
The set-up was that 20 women were present on the livestream in an effort to win a date with the Canadian multi-hyphenate.
One of those women was British OnlyFans creator Lily Phillips, who made a name for herself with elaborate X-rated videos.
British creator Lily Phillips attended the stream as one of the 20 women hoping to win a date with Drake.
However, Phillips and Drake's interactions caught fan's eyes for all the wrong reasons.
In the clip, the OnlyFans creator readily describes herself as a "super sl*t" but says that she's ready to now "rebrand" as Drake's wife, however many fans deemed their interaction in the video as "cringe," and it's definitely not a comfortable watch seeing the two interact on camera.
Drake the commented on Phillips' tan, saying she was on "peptides" trying to "get to [my] color," before adding, "I don't know if we're allowed to say that"
Despite her best try, Phillips wasn't picked as one of the finalists in the video.
For almost her entire career as a content creator, Lily Phillips has been embroiled in one scandal into another.
Her online career has been built around her determination to push sexual boundaries. She came to fame after once claiming to have slept with 101 men in the same day, a similar tactic employed by her equally controversial peer Bonnie Blue.
One particularly controversial tactic Phillips has employed on her social media has been a "before vs after" trend when she's filming her videos, which has drawn criticism from both viewers and sex and relationship experts.
A particularly long-running controversy throughout Phillips' recent career has been that sometimes the identities of the men involved in her content being revealed, which has had consequences in real life.
One woman deemed Phillips a "homewrecker" after discovering that her father had taken part in one of her videos, stating that his involvement had fractured his relationship with his family.
And it's not just the men, either. A female content creator who took part in a 'backdoor' trend video with Phillips went on to reveal that after husband found the explicit video online has filed for divorce.
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Adult‑content creator Lily Phillips has spoken publicly about her sexuality for the first time — and said she can envision a future with a woman. In a candid interview, the star, previously best known for on‑screen relationships with men, described how dating women has opened her eyes to a different kind of connection.
The change in her outlook comes as she appears on the dating show Blind Matchmakers. Rather than basing chemistry on looks, contestants rely solely on personality, voice, and attraction beyond physical appearance. Phillips said being on the show felt “super fun” and gave her a fresh perspective.
She also admitted that love is not a priority right now. With her focus firmly on her career, she said she does not want to start dating until she can devote herself completely to a relationship.
Phillips told The Mirror that “in the year 2025, it’s not that much different to dating straight people.” She added: “I think around bisexuality, people are more open these days. I’ve never felt any judgment from that, so to me, it’s just like dating boys.”
Lily Phillips has made a name for herself in the adult industry. Credit: Lily Phillips/Instagram
Talking about meeting women on Blind Matchmakers, she said: “I think women’s relationships are amazing, you just won’t ever find a connection like that with a man. Women, we understand each other more, I think.” She went on: “You’re best friends, but you’re also sexually attracted, and you have sex – that is my ideal relationship.”
On the show, Lily was matched with social‑media influencer Lani, and the two shared noticeable chemistry. However, Phillips revealed their relationship did not progress beyond friendly messages. She described Lani as “a powerful woman” who knows herself, but acknowledged: “We have exchanged a few messages, but it’s been niceties, not anything more.”
Despite that, Lily admitted to being open to a same‑sex relationship in the future. She said: “I do consider a high chance it might be a woman,” but clarified she is not ready to date for now. Instead, she wants to remain “selfish” and focus on building her career before committing to a relationship.
Credit: Instagram/Lily Phillips
Phillips said the dating show let her approach relationships differently than through mainstream apps where appearance is often everything. She reflected that many people "filter out" potential dates based purely on looks or a few photos before even meeting.
For her, personality and connection matter more. Even though her past relationships — both on‑ and off‑screen — have been mostly with men, she signalled that could change when the time is right.
Her message was clear: she is exploring, open‑minded, and realistic. She is not rushing into anything but remains open to love if the right person — woman or man — shows up.
An OnlyFans star who slept with 101 men in a single day has unveiled a huge mistake that she made during the challenge.
As you've probably seen while scrolling social media, Lily Phillips has recently become the talk of the town.
The 23-year-old British adult star undertook the challenge of sleeping with 100 men in a single day, and she succeeded.
The event, which sparked both fascination and criticism, has been detailed in a new documentary by YouTuber Josh Pieters, who provided an exclusive behind-the-scenes look.
In one emotional moment, Phillips broke down in tears, reflecting on the physical and emotional toll of the challenge.
“Sometimes you just disassociate... it’s not like normal sex at all,” Phillips admitted. “In my head, I can think of five, six guys, 10 guys that I remember. And that’s it. It’s just weird, isn’t it? If I didn’t have the videos I wouldn’t have known that I’d done a hundred.”
She described the process as “robotic,” saying: “Just one in, one out, it feels intense. It’s not for the weak girls, if I am honest, it was hard.”
Pieters, who documented the experience, aimed to present a nuanced perspective on Phillips’ journey.
“It was vital that we showed as many sides to this complex scenario as possible,” he told news.com.au.
He reflected on witnessing Phillips’ emotional struggle. “Seeing Lily emotionally break down at the end of her challenge was extremely sad... despite her saying this was her ‘fantasy,’ I couldn’t shake the feeling that this was not going to be as easy and happy as she wanted it to be.”
Concerns intensified after Phillips admitted she did not use protection during oral sex with her participants.
In the documentary, she recounted her routine with each man, which began with oral sex.
When asked by Pieters if she used condoms for this part of the act, Phillips replied: “No, I didn’t,” though she confirmed condoms were used for intercourse.
Pieters then asked if she worried about contracting HIV, to which Phillips responded: “Is that where it comes from?”
Appearing surprised, she added: “Really? See, I’ve never really thought about that.”
The exchange has raised alarms online, with many questioning her understanding of sexual health risks.
HIV, which is transmitted through bodily fluids including semen and blood, poses a significant risk in unprotected sexual encounters.
Medical professionals have raised alarms about the extreme physical and psychological risks associated with such challenges.
Dr. Zac Turner, a preventive health specialist, warned about the potential dangers of undertaking such a physical challenge.
“Sex, at its core, is a physically demanding activity that engages various muscles, the cardiovascular system, and the release of endorphins,” he told the New York Post.
While moderate sexual activity is beneficial, Turner emphasized that the sheer magnitude of Phillips’ challenge could lead to severe harm.
“Fatigue diminishes the pleasurable aspects, and the constant physical exertion transitions from beneficial to harmful,” he explained. Risks include tearing, bruising, soreness, and long-term strain on the body.
Despite the backlash, Phillips remains focused on her ultimate goal: breaking the world record for the most men slept with in 24 hours.
The current record, set in 2004 by adult film star Lisa Sparks, stands at 919 men, and Phillips is aiming to sleep with 1000 men in 24 hours.
Lily Phillips has opened up about a pretty gross health issue that she's encountered since she slept with 101 men in a day.
In case you haven't heard of her, Phillips is a 23-year-old adult star who is taking the industry by storm.
This time last year, nobody was too aware of her - but fast forward to today and she's all over social media.
Part of the reason is due to the challenges she sets herself, such as her hopes to sleep with 1000 men in a single day.
To practice for such a huge target, the 23-year-old slept with 101 men in a day and it has sparked a lot of controversy.
YouTuber Josh Pieters followed Phillips on the big day and provided a behind-the-scenes look.
In one scene shared on social media, Phillips appeared visibly drained, reflecting on the taxing nature of the experience.
"It's not for the weak girls," she admitted. "If I'm honest, it was hard. I don't know if I'd recommend it."
She likened the challenge to "being a prostitute," describing the day as "intense" and noting it was fundamentally different from typical intimacy.
"It wasn't just having sex with someone; it was one in, one out," Phillips explained.
She then burst into tears and had to be excused from the room.
Well, the emotions from the day aren't the only thing that the adult star has to worry about, as she's now opened up about a health issue she's got from that day and other challenges.
Phillips shared her ordeal in a recent TikTok video, sparking concern among her fans.
“I’ve taken so much liquid in my eyes over the last month or so, that it’s now having a permanent effect on my eyes,” she revealed in the video, while appearing visibly distressed.
In the clip, Phillips is seen sitting on a sofa, her eyes noticeably red and swollen. A man is positioned behind her as she candidly describes her symptoms.
“This video was just the start of it,” she continued. “They were stinging so much here, but now it’s so much worse.”
The admission has alarmed many of her followers, who expressed their hopes that Phillips is seeking appropriate medical treatment.
One person wrote: "Girl it could be clamidia [sic] of the eye. If they start going crusty gem em checked."
In terms of her 1000 men in a day goal, medical professionals have voiced serious concerns about the risks associated with such extreme challenges.
Dr. Zac Turner, a specialist in preventive health, warned about the physical and psychological strain involved.
“Sex, at its core, is a physically demanding activity that engages various muscles, the cardiovascular system, and the release of endorphins,” Dr. Turner told the New York Post.
While beneficial in moderation, he noted that activities of this magnitude could lead to severe physical harm.
“Fatigue diminishes the pleasurable aspects, and the constant physical exertion transitions from beneficial to harmful,” he explained, citing risks such as tearing, bruising, general soreness, and long-term physical strain.
OF star Lily Phillips is racking up millions of views on TikTok with a public sex stunt, essentially exposing it to ordinary people on the street.
Phillips is a British adult content creator and social media figure who rose to international notoriety after participating in a controversial filmed event where she had sex with 101 men in a single day.
The stunt, documented in a viral video titled I Slept With 100 Men in One Day, sparked massive media attention and public backlash. Phillips described the experience as far more taxing than she had anticipated, saying it left her physically and emotionally drained.
The video reignited long-standing debates about the limits of adult content, personal agency, and the health and safety protocols - or lack thereof - in such extreme shoots.
Following the 101-men event, Phillips found herself at the center of another uproar when she posted what appeared to be a pregnancy announcement on social media, only for it to be revealed later that it was staged as part of a role-play scenario.
Critics called the move insensitive, especially to individuals struggling with infertility or pregnancy loss. Many accused her of using emotionally manipulative tactics to gain attention, and some demanded accountability from the platforms hosting her content.
Compounding the controversy was her alleged use of a short-term rental, reportedly an Airbnb, to film the 101-men event without the knowledge or consent of the property owner. Reports suggested that Airbnb considered banning her following the incident.
The situation raised concerns about consent, liability, and the growing trend of adult creators using residential properties for commercial filming purposes without disclosing their intentions.
Phillips has also drawn criticism for videos involving elderly men in care-home-like settings. One such clip showed her engaging in flirtatious behavior with older men, which many viewers interpreted as exploitative.
Some labeled it “fake” and “gross,” arguing that she crossed ethical lines for the sake of virality. While Phillips has consistently defended her choices as expressions of personal freedom and feminism, these stunts have polarized audiences and intensified discussions around consent and performative sexuality.
As public attention mounted, Phillips disclosed that she had received death threats and was confronted in real life by angry partners of her subscribers. She expressed distress over being screamed at in public and described the emotional toll of being the subject of such intense scrutiny. Despite this, she has not backed away from her platform and continues to promote her work, albeit with a more subdued public presence.
Known as the 'c*m walk' - a stunt that Phillips has taken part - it in involves her walking around in public with her face covered in male ejaculate – equivalent to an extreme version of the 'walk of shame'.
The videos have since received millions upon millions of views on platforms like TikTok and Instagram.
According to sex therapist Annabelle Knight, who spoke with Metro UK: "Facials have been a staple in p*rn for decades, however the idea of someone deliberately walking around after sex with semen visible on their face is far newer."
She added: "There isn't a a clear moment when the term entered the sexual vocabulary, but it seems to have gained traction more recently with the rise of amateur content platforms like OF, where bold and attention-grabbing stunts are part of the culture."
Credit: lilyphillip_s / Instagram.
Though with the viral 'c*m walk', however, there is the issue of consent.
As Dave Savage explained on his Savage Love podcast that the real issue with it is whether people or passersby notice. "Somebody's got to clock your face, and then somebody's got to realize what it is that's all over your face," he stated.
Knight greed, stating: "The key issue is that sex and anything overtly sexual should always involve consent from everyone subjected to it."
She continued: "It's one thing to enjoy roleplay or exhibitionism in private, but when it moves into public spaces, there's a responsibility to think about others, so it does raise important questions about exposing others to sexual content without their agreement."
Lily Phillips has made a name for herself in the adult industry. Credit: Lily Phillips/Instagram
Legally, however, this would not be classed as sexual assault, according to Tony Wilbraham - a criminal defense lawyer at Olliers Solicitors.
"I do believe this could amount to the offence of 'outraging public indecency' but only if people (a) realised that person was walking round with ejaculate on them, (b) if the police arrested them while it was happening and could prove it was semen and (c) if at least two members of the public witnessed it," he said.
"I have heard of this before, but I suspect if people did this, most people wouldn't realise what was going on, and even if they saw them, they wouldn't necessarily realise what the material was.
"If the Police got a complaint that someone was doing this and didn't arrest them in situ, then it would be difficult to prove what they were doing."
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