Pete Davidson's Romantic Timeline
I've spent way too many late nights compiling relationship histories for pop culture pieces, and Pete Davidson's dating track record is one of the more well-documented ones in modern celebrity culture. The public narrative started gaining traction around 2018 when he and Ariana Grande made things official, but his romantic history actually extends back years before that moment. The core relationships worth tracking, in chronological order, are: Casey Wilson (2012-2014), Chloe Walsh (2014-2015), Frances Bean Cobain (briefly in 2015), Sara Bareilles (around 2016), Catherine Reitman (2017-2018), Ariana Grande (2018-2020), Kim Kardashian (2022-2023), and Hayley Bailey (2024-present, though their status has fluctuated publicly). That's the short version. What people miss when they're just scanning headlines is the pattern underneath. Pete tends to date women who are already established in their careers—singers, actors, musicians—with a notable gap between high-profile relationships. The 2015-2017 stretch where he was relatively quiet is telling. He was dealing with his mother's cancer diagnosis and his own mental health treatment, which contextualizes why the public relationships slowed down during that window.
When I'm building these timelines for articles, I run into a specific problem with Pete's case: the gap between what's documented and what's actually happening. Celebrity PR teams are good at keeping things private, and Pete himself has been transparent about therapy and mental health in ways that make him less likely to share relationship details publicly. My workaround has been to cross-reference podcast appearances, interview clips, and social media activity from the partners themselves, not just entertainment news outlets. People like Frances Bean Cobain and Casey Wilson have spoken about their exes on their own terms, which gives you a more accurate timeline than gossip sites alone. The Frances Bean Cobain connection is one of those things that gets misreported constantly. They were linked in early 2015, but it was extremely brief—weeks, not months—and both sides kept it low-key. Entertainment outlets inflated it because of the Cobain name association, but the actual relationship duration was minimal. Similarly, the Sara Bareilles timeline gets murky. There were photo sightings and vague acknowledgments, but neither party confirmed anything substantial. I treat those as "likely dated" rather than confirmed relationships until there's direct documentation.
The Ariana Grande Period
The Grande relationship is the most analyzed one, partly because it happened during peak social media era and partly because of the age difference and trauma dynamics that people love to dissect. They announced their engagement in May 2018 and called it off in January 2020. That's roughly two and a half years together, with the engagement period covering about six months of that timeline. What's interesting about tracking this relationship is how much public information came from Ariana's side. Her album Sweetener and subsequent projects contained direct references to Pete, and she's been more vocal about their split than he has been in interviews. When building accurate timelines, you have to account for which partner is driving the narrative. In this case, Ariana has been remarkably open, which gives us better documentation than most celebrity relationships from that period. The mental health aspect here is worth noting because it affects how we interpret the relationship's trajectory. Pete has spoken extensively about BPD and therapy, and Ariana has discussed her own trauma history. Their relationship existed within a context where both were actively processing significant life events, which complicates any simple "why it ended" analysis.
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Kim Kardashian and the Current Phase
The Kardashian relationship ran from mid-2022 through mid-2023, roughly a year together. They got engaged in April 2023 and called it off by July 2023. The speed of that engagement-to-breakup cycle is what people remember, but the actual dating period before engagement was shorter than the total relationship length suggests. Hayley Bailey represents the current chapter, though their public appearances have been sporadic. They were spotted together in late 2023 and early 2024, with some uncertainty about whether they're still together as of mid-2024. The The Little Mermaid star dynamic adds another layer to how these relationships play out publicly, given both of their high-profile careers. One limitation I have to acknowledge when documenting Pete's dating history: there are likely relationships or flings that never made public record. He's been in Los Angeles and New York social circles for over a decade, and not every connection gets photographed or discussed on podcasts. Any complete list is inherently incomplete by definition.
The pattern that does emerge consistently is that Pete dates women slightly older than him or in their late twenties to early thirties range, almost always with established careers in entertainment or music. He tends to move quickly from dating to engagement when things work, then ends things decisively when they don't. That's the observable pattern without getting into speculation about compatibility or personal dynamics. If you're researching this for anything beyond casual curiosity, I'd recommend starting with primary sources—interviews, podcast appearances, and statements from the people involved—rather than relying on tabloid coverage, which tends to compress timelines and amplify drama for clicks.
