Kristin Cavallari Puts Harry Jowsey's 'Gigantic' Private Part On The Spot

By Afouda Bamidele on May 5, 2025 at 7:00 PM EDT

A photo collage of Kristin Cavallari and Harry Jowsey
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Harry Jowsey's secret is not safe with Kristin Cavallari.

The YouTuber reportedly shared an intimate picture with the reality TV star, and she could not stop raving about his impressive volume.

Kristen Cavallari is riding on the euphoria of the trailer of her new E! docuseries "Honestly Cavallari: The Headline Tour," which comes out May 5, 2025.

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Harry Jowsey Outed By Kristin Cavallari For Raunchy Gesture

Harry Jowsey at Borderlands LA Fan event
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During a recent podcast taping, Cavallari made headlines by calling out Jowsey for sending her an explicit photo, which she referred to as "a d-ck pic." 

This revelation was featured in the trailer for her new E! docuseries, and it left Jowsey visibly embarrassed, as seen when he playfully thumped himself on the forehead with his microphone.

The trailer also captured a moment where Cavallari showed her blurred-out phone to her best friend, Justin Anderson, during a car ride, prompting him to gasp in surprise at the size of the photo, saying, "It's gigantic."

Additionally, backstage, Jowsey inquired whether fans would see more of Cavallari, precisely "her chest" during the live show, to which she responded humorously, saying, "Probably. Hell yeah!" 

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The interaction between Cavallari and Jowsey has garnered attention since he first appeared as a guest on her podcast back in January, where their flirty exchanges made headlines.

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The Uncommon James Founder Reportedly Went Out With A Famous Romantic Interest

During the conversation, Jowsey playfully expressed his willingness to end his celibacy. He jokingly declared, "I'm the man. I'm taking charge," responding to Cavallari's comment about wanting a "manly man." 

Meanwhile, Cavallari, previously married to Jay Cutler from 2013 to 2022, has been linked to various men, including Morgan Wallen and Mark Estes.

In the trailer released today, Monday, Anderson revealed that Cavallari also recently went on a date with a star from "Top Gun," though the actor's name was not disclosed. 

Cavallari appeared surprised at this revelation, but later mentioned in a confessional that the purpose of her tour was to discuss the most scandalous headlines surrounding her. While onstage, she emphasized her desire to create buzz, stating:

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"I want to give them something to write about! Let's give them some damn headlines."

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The TV Star's Blast From The Past Reconnected With Her On The TourĀ 

Kristin Cavallari at 2022 iHeartRadio Music Festival
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Speaking of romantic interest, the reality star and her 8th-grade ex-boyfriend had an awful reunion, leaving a bitter taste in her mouth and influencing her decision to review their relationship.

As noted by The Blast, Cavallari was taken aback by the reality of her former boyfriend, who had been her first sexual experience. He turned out to be completely different from what she had anticipated.

In her March 25 recap episode, Cavallari shared an interesting moment from her "Let's Be Honest" podcast tour, where she was joined on stage by a surprise guest, her middle school boyfriend, Johnny.

Cavallari shared that they got intimate for the first time in the 8th grade, which led to her losing her virginity to him. Following their contact, Cavallari was prompted to reflect on the other relationships she entered into after they got together.

The reality star and Johnny's time together profoundly impacted her life, filling it with cherished memories and warm feelings of love. She vividly remembers reconnecting with Johnny, where they spent a few weeks engaging in meaningful conversations that led to a pivotal moment for both of them.

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Cavallari Was Left Dejected By Her Brief Romantic Reunion

Kristin Cavallari at GMA on April 15 2019
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In a candid reflection, the former reality star shared her experience leading up to her performance on stage with Johnny, noting his noticeable nervousness. 

To alleviate his discomfort, she asked him questions in advance to help set him up for success. However, during the performance, his behavior took her by surprise as he seemed to channel his anxiety into giving her a hard time, leaving her feeling let down. 

She contrasted his stage persona with the warmth he showed her afterward when he greeted her with a kind kiss and expressed a desire to spend time together. 

Eventually, Cavallari recognized that her strong feelings about the incident were heightened by exhaustion and the day's pressures. She ultimately viewed the experience as a significant reminder of her personal growth, especially regarding her relationships with men.

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Kristin Cavallari Is Patiently Waiting For The Perfect Match

Kristin Cavallari seen out in NYC IN May 2019.
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After sharing her feelings with friends about Johnny's stunt, she expressed that the experience left her feeling "bummed" and prompted her to reflect on her relationships.

She voiced her frustration about being put down by the men in her life, yet reaffirmed her self-worth with a powerful statement: "I'm enough. I love myself." This realization has inspired her to focus on self-love rather than seeking validation from others.

Having faced challenges in her past relationships, particularly with her ex-husband Jay Cutler, with whom she shares three children, she is now determined to start anew in her dating life.

Following their split in 2022 and a fleeting relationship with influencer Mark Estes, she began exploring dating apps after their breakup in September 2024. However, the reality star is now reconsidering this approach, questioning whether these interactions are genuinely beneficial or merely fleeting distractions.

Moving forward, she plans to invest her energy into self-care and remains open to the idea of a meaningful relationship when the right person comes along.

The new docuseries by Kristin Cavallari will definitely have all the sizzling hot tea!

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