Singer and influencer Olivia O’Brien has publicly re-examined her past relationship with comedian Pete Davidson, sharing critical comments about how their short-lived romance came to an end.

The dynamic between the two resurfaced after O’Brien commented underneath an Instagram post addressing Davidson’s recent controversial critiques regarding female influencers.

In her online remarks, O’Brien spoke about the abrupt ending of their romance and shared new details about their timeline.

Olivia O'Brien. Credit: Instagram / @oliviaobrien

According to O’Brien, the pair were involved with one another during the fall of 2020. She claimed that despite maintaining near-constant communication at the height of their connection, she ultimately learned the relationship had ended through public social media coverage rather than a direct conversation.

Reflecting on the situation on social media, O’Brien called out Davidson's behavior during that period. "I was dating him in 2020 and found out we were no longer together by seeing on snapchat daily mail that he went public with a more famous woman lmaooo. he is an absolute joke of a human being," she wrote.

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Credit: Instagram

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In a follow-up response to another user on the platform, O’Brien elaborated on how involved they were right up until the sudden shift.

She highlighted the contrast between their level of daily interaction and the way things concluded. "Not sure how he has the time considering we were texting 24 hours a day and falling asleep on facetime when we weren’t together. busy boy! lmfao," she noted.

The recent statements mark a noticeable change in tone compared to how O’Brien previously addressed the subject.

Back in 2022, after pop culture gossip account Deuxmoi published an anonymous submission linking Davidson to actor Phoebe Dynevor, O’Brien confirmed the rumor during an appearance on the podcast BFFs With Dave Portnoy, Josh Richards, and Brianna Chickenfry.

During that interview, she originally described Davidson in a far more positive light.

Pete Davidson had a short-lived romance with Olivia O'Brien. Credit: Dia Dipasupil / Getty

"Yeah, Pete. I didn’t think that anyone knew about that, I really didn’t.…Um, yeah, we - um, that’s true. Nice guy. He’s hot, he’s funny, and he’s sweet, he’s a really sweet guy. That was October of 2020. He texted me and was like, ‘I’m seeing someone else so I can’t.’… I cannot believe you guys found that, that’s really crazy, you’re the first people to ever ask me about that and I really thought that no one knew about that. Breaking news. Oh, god. Two years later."

Social media clarification

Following the podcast episode, the story gained traction online, prompting a swift response from Davidson's management team.

A representative for the comedian issued a statement to E! News denying that any formal romantic relationship had taken place between the two stars.

According to the statement from his team, "there is no truth to this" and the pair "were friends and hung [out] a few times".

In response to the representative's denial and the subsequent media coverage, O’Brien posted a clarification to her Instagram Story at the time to address the growing speculation.

Credit: Instagram / @oliviaobrien

"News outlets are taking things I said in an interview (after being asked a VERY specific question) wayyy out of context. I never claimed to date anyone. Stop trying to start weird drama over me texting someone 2 years ago. Jesus Christ."

Featured image credit: Dia Dipasupil / Getty

Pete Davidson has spoken out about his ex, Ariana Grande, who he dated in 2018, during a new interview.

The comedian, 32, and the singer, 33, dated between May and October 2018, and appear to have a lot of respect for one another after splitting up.

Grande made recent headlines after announcing she would be stepping back from the limelight after completing her Eternal Sunshine tour following a 10-night stint in London.

The 'Thank U, Next' star had faced scrutiny over her appearance, particularly around her weight loss, with many fans expressing concern for her health.

Pete Davidson and Ariana Grande dated back in 2018. Credit: Kevin Mazur / Getty Images

Her spokesperson said in a statement on August 2: "She looks forward to finishing the tour and ending it on a high note, both healthily and happily, and then taking a much-deserved break from public-facing work and appearances, which has led to endless, ongoing public scrutiny.

"This tour has been a beautiful experience for her. She loves her fans and has loved every minute of this tour so much."

When asked about the public discourse around Grande's appearance, Davidson told Variety: "I don’t like it at all. It’s not cool. She’s a really strong person — I’ve witnessed it — and I don’t understand it.

"She knows how to handle this stuff though. She’s been around. So she’ll be OK, but I think it’s f**ked up."

He also shared his frustration at the attention put onto his dating life in comparison to his career, adding: "It’s been over a decade. My work and my relevance is super overlooked, and it’s confusing to me.

"I’m still only 32, but I have really crazy credits: nearly a decade at ‘SNL’; I hosted a year after I left; I worked with [Craig] Gillespie [on Dumb Money], and [James] Gunn [on The Suicide Squad] and [Doug] Liman [on Bitcoin] and Leitch and Judd and Edie and Pesci.

"What the f**k do I have to do? And look, I get it — I’ve dated a lot of people. But so has everyone else! Everyone is f**king everyone in this business! Everyone!

"And for some reason it’s zeroed in on me, and I can’t feel sorry for myself because I put myself in those situations, but everyone else is doing it. I was in my 20s. Am I not supposed to f**k around and do drugs and have fun and be in Hollywood like everybody else? Sorry, everyone!"

Ariana Grande faced a lot of scrutiny over her appearance recently. Credit: Amy Sussman / Getty Images

Davidson also addressed being the subject of some of Grande's songs, joking: "There should be a group for us.

"It’s something that comes up once in a while. But I think Ariana’s f**kin’ cool and immensely talented and an awesome girl. We’re not texting or whatever, but we’re cool."

Featured image credit: Kevin Mazur / Getty Images

The reason why Pete Davidson and Kim Kardashian will not be seated next to each other at the Met Gala has been revealed.

The annual fundraiser for the Metropolitan Museum of Art’s Costume Institute in New York returns on May 4, bringing together some of the biggest names in fashion, film, and music.

But while fans focus on red carpet looks, organizers are busy working behind the scenes to make sure there are no uncomfortable run-ins once guests take their seats.

Davidson dated Kim K for around 9 months. Credit: Gotham / Getty

Inside The Seating Plan

Eaddy Kiernan, who organizes Vogue’s Met Gala each year, has shared just how much effort goes into arranging the seating chart.

"We start with a seating document when the names come together in December," Kiernan previously told Vogue. "The actual seating chart doesn’t come together until about a month before the event, when we get a sense for the layout of the room, and the flow of the evening."

Her team carefully considers every pairing, aiming to create genuine connections between guests while steering clear of past relationships.

"Our ideal pairing would maybe be two people who we think will just get on like a house on fire, but who may not even realise that they have a lot in common," she divulged. "So with each person, we really do take time to think, ‘What will they talk about?’"

She added: "We try and think a lot about sight lines and where people have sat in the past. And we try to make sure someone isn’t staring into the eyes of a former flame."

Kim Kardashian and Pete Davidson broke up. Credit: Gotham / Getty

Star-Studded Lineup

As always, the event is being hosted by Anna Wintour, even after stepping down as Vogue's editor-in-chief in June 2025 following nearly four decades in the role.

This year’s co-chairs include Beyoncé, Nicole Kidman, and tennis star Venus Williams, with hundreds of celebrities expected to attend.

The planning team will also be mindful of other high-profile breakups. Kidman’s former husband, Keith Urban, for example, is unlikely to attend.

The ex-couple last appeared together at the event in 2024 before splitting months later and finalizing their divorce in January 2026.

The event is being hosted by Anna Wintour. Credit: Taylor Hill / Getty

The 2026 Theme Explained

The 2026 Met Gala will center around the theme "Costume Art," with a dress code of "fashion is art," per USA Today.

The exhibition aims to explore the relationship between clothing and the human body, pairing garments with artwork to highlight how fashion functions as an artistic expression.

Per the title, "Costume Art will "examine the centrality of the dressed body" by interspersing garments and artwork "to create pairings that not only illuminate the indivisible connection between clothing and the body but also the complex interplay between artistic representations of the body and fashion as an embodied artform".

Max Hollein, the Met’s director and CEO, said the exhibition will "highlight The Met's unique ability to position fashion within the context of more than 5,000 years of art represented in its collection."

The exhibition opens May 10, 2026, and will run through January 10, 2027.

Featured image credit: Paul Morigi / Getty

Pete Davidson caused instant controversy after taking aim at Charlie Kirk during his appearance at The Roast of Kevin Hart on Netflix.

The comedian appeared at the live-streamed event from the Kia Forum in Los Angeles on Sunday, May 10, where he delivered a string of savage jokes aimed at fellow comic Tony Hinchcliffe and rapper Kanye West.

Davidson, who has built a reputation for pushing boundaries during celebrity roasts, wasted no time going after Hinchcliffe, a comedian often associated with right-leaning comedy circles and figures like Joe Rogan. The pair have clashed before, and Davidson made it clear there would be no holding back.

Pete Davidson. Credit: Dia Dipasupil / Getty

Pete Davidson’s Charlie Kirk joke shocks roast audience

Charlie Kirk, the conservative commentator and founder of Turning Point USA, was assassinated in September last year, sparking outrage from conservatives over jokes and memes related to his death.

Vice President JD Vance and then Attorney General Pam Bondi previously warned there could be consequences for people making light of the killing. Despite that, Kirk has continued to be widely referenced in memes online.

Charlie Kirk, the conservative commentator and founder of Turning Point USA, was assassinated in September last year. Credit: Justin Sullivan / Getty

During his set, Davidson opened with a brutal jab at Hinchcliffe’s appearance before escalating things even further.

“Tony Hinchcliffe is here, looking like both a child molester and the doll they give the child to show where he touched them.

"Tony reminds me of Charlie Kirk, in that he's definitely been on camera letting a guy unload in his throat."

The crowd reacted with a mixture of laughs, groans and stunned silence as the joke landed inside the arena.

Davidson then continued attacking Hinchcliffe and his podcast Kill Tony, adding: “Please someone f*cking 'Kill Tony'. Tony, nothing you say tonight will hurt my feelings. I was in a beef with Kanye so I've taken shots from better gay Nazis."

Kanye West also caught strays during the roast

Davidson’s Kanye West remark appeared to reference the rapper’s past antisemitic comments, which Kanye later apologized for publicly.

The pair have a long-running history after Davidson dated Kanye’s ex-wife Kim Kardashian. Back in 2022, Kanye repeatedly targeted Davidson online and referred to him as “Skete” in a series of social media posts.

Kanye West. Credit: Gotham/Getty

Clips of the roast quickly spread across X following the Netflix broadcast, with viewers split over whether Davidson crossed the line.

“It’s crazy that we live in a timeline where it's acceptable to speak like this on an innocent man,” one person wrote online.

“He is joking but he is serious at the same time. These people are glad that you're gone because they don't see you as human.”

Others defended Davidson and argued the backlash was overblown.

“Oh man, the angry comments here. If you're mad about Peter mocking either Charlie Kirk or tony Hinchcliffe, you're a loser,” another commenter fired back.

One viewer summed up the chaotic mood of the roast by writing: “Pete Davidson really work up and chose maximum chaos for this roast.”

Online reaction quickly split viewers

The backlash against Davidson continued to build online, with some viewers accusing the comedian of trying too hard to stay controversial.

“Pete going savage on Tony with Charlie Kirk jab is a sad attempt to stay relevant and the vibe didn't match. He was once cool,” another critic wrote.

Others, however, argued the entire point of a celebrity roast is to push boundaries and shock the audience.

The clip has continued circulating widely online, with debate raging over whether Davidson’s comments went too far or simply matched the anything-goes nature of roast comedy.

Featured image credit: Steve Granitz / Getty

Pete Davidson isn’t one to let a joke slide — especially when it’s about his, uh, measurements.

And after ex-fiancée Ariana Grande, 32, made a now-infamous comment about his manhood, you know the comedian had something to say about it.

For those who missed the drama (where have you been?), the whole thing started when Grande dropped a track named — wait for it — 'Pete Davidson' on her 2018 album, Sweetener.

The superstar couple had embarked on a whirlwind romance that same year and eventually got engaged in June, just weeks after making their relationship public.

However, in October, the pair officially ended their engagement and split, but they haven't shied away from talking about each other, with Grande even getting a little too intimate with the details sometimes.

Pete Davidson and Ariana Grande were engaged at one point. Credit: Jeff Kravitz / Getty

Fans wanted to know about one thing

As with any fanbase on social media, Grande's fans tended to pry, though one specific topic kept cropping up.

One particularly curious soul took to X to ask: "How long is Pete?" (Meaning the song, obviously. But also... not.)

"OH AS IN THE INTERLUDE NOT AS IN... ANYWAY," the fan quickly followed up.

Cue Ariana, ever the cheeky queen, who took the joke and ran with it, replying: "Like 10 inches?... Oh f***... I mean... like a lil over a minute."**

And just like that, the internet lost its mind. While some fans cackled at the overshare heard ‘round the world, others were genuinely impressed — but Pete? Well, he had his own response.

Davidson responded to Grande's claims

Instead of sulking, Davidson, 32, did what he does best — turned it into a punchline. During a 2020 Saturday Night Live skit, he hit back by claiming: "I don’t like that she talked all that s*** for my p*nis.

"Everything is huge to her. Why would she tell everyone that I have a huge penis? So that every girl who sees my d*** for the rest of my life is disappointed."

Oof. Points for comedic timing!

Later, in an interview with Charlamagne Tha God, Davidson took a more chill approach, admitting he wasn’t really mad, just rolling with the punches.

"She’s the queen of shade," he said. "I get it. That’s her job. … She has music to it, I get it. I hope people feel the same way about my jokes."

Pete Davidson responded to Grande's claims, years later. Credit: Eric Charbonneau/Amazon MGM Studios via Getty Images

The superstars have moved on

It's been eight years since their star-studded engagement, but the stars have moved on from each other in life.

Davidson now has a child with partner Elsie Hewitt, 29, as the model welcomed their daughter into the world on December 12 last year.

The couple announced the birth of their child on social media a week later, and revealed her name, Scottie Rose Hewitt Davidson, seemingly a tribute to Davidson's late father - Scott.

As for Grande, she has been dating her Wicked co-star Ethan Slater since July 2023, following his divorce from partner Lilly Jay... something that Jay has not been silent about.

In the 1,807-word memoir for The Cut, Jay opened up about the painful dissolution of her marriage, her life as a single parent, and her struggle to reconcile personal heartbreak with sudden public scrutiny.

Jay’s work focuses on supporting new mothers through the challenges of pregnancy and early parenthood, and she had long sought to maintain anonymity for the sake of her clients.

She removed herself from social media at 18 to safeguard her privacy. However, the events surrounding her high-profile divorce have left her life and profession entangled in public discourse.

“No one gets married thinking they’ll get divorced, in the same way we don’t board a plane expecting to crash. But I really never thought I would get divorced,” Jay writes.

“Especially not just after giving birth to my first child and especially not in the shadow of my husband’s new relationship with a celebrity.”

Ouch.

Featured image credit: Cindy Ord/Getty Images