The self-described “Malibu’s Cowboy” skipped college and went straight to the ranch — and brought enough drama back with him to fill a season.
Dylan Wolf is a 24-year-old Calabasas native and one of the central figures in Netflix’s new reality series “Calabasas Confidential.” He attended Calabasas High School and, while most of his friends went off to college after graduation, Dylan took a different path — heading straight to work on a Malibu ranch. He calls himself the “Malibu’s Cowboy” and is a professional bull rider who competes in local rodeos, with a separate social media page dedicated to that work.
Netflix describes his current chapter simply: “Since high school, Dylan has worked hard on bettering himself and becoming a Calabasas cowboy.” He told Tudum, “I’d describe myself now as badass.”
What Does Dylan Wolf Do?
Dylan parlayed his ranch experience into social media content, posting under his own name as well as the pseudonym “Malibu’s Cowboy.” On the show, he talks openly about getting sober after a rough post-high school stretch — he tells Emma in Episode 1 that he got into horseback riding as a form of therapy and that “rock bottom is where you stop digging.” He now works on a ranch in Malibu.
Dylan Wolf’s Drama on ‘Calabasas Confidential’
Dylan arrives in Season 1 carrying the most romantic wreckage of anyone in the group. Netflix describes his relationship history with Jemma Durrant as an “ex-fling,” though Dylan himself refuses to frame it that way on the show — repeatedly insisting the two were never anything official. Jemma sees it differently. In the trailer, she says, “He didn’t just break my heart. He literally tore me apart.”
The tension compounds immediately when Dylan shows up to Jemma’s party with Emma Medrano — another woman from his high school past. His connection to Emma becomes its own source of conflict, fueling the feud between Jemma and Emma that dominates the early episodes.
His past romances continue to create tension throughout the group. The show captures him as someone who senses the chaos he causes but doesn’t always move to stop it. As one cast member puts it in the trailer: “Dylan loves attention. He wants you to be upset.”
Dylan & Suede Brooks
Suede comes into the group not knowing Dylan at all — it’s Jemma who fills her in on who he is and what he put her through. Which makes what unfolds afterward sting a little more. By Episode 2, Dylan is already flirting with her at Kimora’s party openly enough that Jemma notices from across the room. Preston Pippen clocks that they left the party together.
Suede is upfront with Jemma about it. After the party, she tells her she gave Dylan a ride home and that it was nothing more than that. Jemma believes her. Then a TikTok surfaces — Suede doing the “something to take the edge off” trend with Dylan — and the optics shift. At a group beach day, Suede spends the afternoon between Dylan’s legs, her head in his lap, barely acknowledging Jemma or Nicole. Jemma is hurt. Nicole is watching, and starts wondering what it says about Suede’s loyalty more broadly.
Whatever is or isn’t happening between Suede and Dylan, it isn’t simple. By Episode 3, the two are at a sushi dinner together, and when Dylan pushes her on communication, Suede thanks him for dinner mid-meal and walks out. She tells Nicole he was being a prick. She also tells her mom she’s seeing someone but doesn’t know where it’s going.
For Dylan, it tracks. He’s drawn to complicated situations, and Suede is the most complicated one available.
Dylan Wolf’s Dating Life Off the Show
Dylan was spotted holding hands with Delilah Hamlin — daughter of “Real Housewives of Beverly Hills” star Lisa Rinna and actor Harry Hamlin — in November 2025. The two have been flirting online since, though neither has confirmed the relationship publicly.
Dylan Wolf’s Social Media
Dylan posts on Instagram under both @dylannwolf and @malibuscowboy.
What Does Dylan Wolf Bring to ‘Calabasas Confidential’?
Dylan is the rare cast member who actually left Calabasas, rebuilt himself somewhere quieter, and came back changed — or at least trying to be. The cowboy hat, the sobriety, and the ranch work aren’t an act, but his track record with women keeps pulling him back into the same cycles he says he’s moved past. That tension between who he was and who he’s working to become is what makes him compelling to watch. He’s not the villain, but he’s not quite reformed either.
Calabasas Confidential Season 1 is streaming now on Netflix.
Get to know more ‘Calabasas Confidential’ cast members:
- Who Is Suede Brooks on ‘Calabasas Confidential’? Meet the Model & Influencer Joining the Netflix Cast
- ‘Calabasas Confidential’: Jodie Woods Has Her Own Story to Tell
- ‘Calabasas Confidential’: Hercy Miller’s Story Goes Beyond His Last Name
- Who Is Alexie Olivo? “Calabasas Confidential” Cast Member Explained
- Who Is Preston Pippen on ‘Calabasas Confidential’? Scottie & Larsa Pippen’s Son Is Ready For His Own Spotlight
For more ‘Calabasas Confidential,” check out our “Calabasas Confidential” Page.
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