The Viall Files

E1058 - Going Deeper with Austen Kroll

January 7, 2026

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  • Austen Kroll's initial hesitation to appear on The Viall Files stemmed from past comments Nick Viall made about Southern Charm being boring, though he ultimately joined as part of a planned series of interviews with the cast. 
  • Austen Kroll attributes his commitment phobia and relationship patterns partly to the tragic loss of his older sister when he was seven, noting that his younger sister's birth served as a 'family rebirth' afterward. 
  • The friendship dynamics between Austen Kroll, Craig Conover, and Shep Rose are complex, characterized by calling each other out for mistakes, but Kroll deeply questioned Craig's loyalty after Craig used a sensitive rumor against him during a filmed confrontation. 
  • Austen Kroll detailed the necessary shift in behavior required when transitioning from being single for a long period to being in a committed relationship, citing his own experience with Nellie. 
  • Austen Kroll believes Shep likely regrets his breakup with Taylor, viewing her as "the one who got away," despite Shep's framing of their past dynamic. 
  • Austen Kroll and Sally have grown close since the last season, with Sally being complimentary toward him, and they are currently close friends, though not romantically involved. 

Segments

Austen’s Reality TV Arrival
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(00:00:38)
  • Key Takeaway: Austen Kroll joined Southern Charm in Season 4 based on Shep Rose’s recommendation, initially not knowing other cast members like Craig.
  • Summary: Austen Kroll was introduced to Southern Charm in Season 4 after Shep Rose recommended him, and he initially only knew Shep among the cast. He found jumping into the established group, including large personalities like Catherine and Thomas, daunting, relying on Chelsea Meisner as a life raft early on. Before reality TV, Kroll worked as a territory sales manager for a brewery in the Southeast.
Betting on Self and Reality TV
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(00:07:19)
  • Key Takeaway: Kroll quit his stable beer sales job after one season of Southern Charm, viewing the decision in retrospect as a ballsy move requiring ‘blind optimism’ or delusion.
  • Summary: Kroll quit his job after one season, realizing the potential of his platform, a move he now recognizes as risky without knowing the future outcome. He believes that a degree of delusion is necessary to bet on oneself, contrasting his path with others who invested heavily in reality TV only to fall away. Kroll suggests that negative experiences on reality television, like a specific video incident, might have been necessary steps leading to his current position.
Family Tragedy and Resilience
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(00:09:50)
  • Key Takeaway: The Kroll family experienced profound tragedy with the death of Kroll’s older sister, Kyle, at age nine, which was followed by the birth of his younger sister, Katie, providing a ‘family rebirth.’
  • Summary: Austen Kroll was seven when his older sister, Kyle, passed away, leading to a ’torturous period’ for his parents before his younger sister, Katie, was born a year and a half later. Katie’s birth is viewed as a complete family rebirth, allowing life to begin again after the dark period. Katie acknowledges Kyle, referring to her as ‘my sister Kyle,’ indicating a spiritual connection maintained by the family.
Commitment Issues and Past Relationships
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(00:14:05)
  • Key Takeaway: Kroll’s therapist attributes his long-standing commitment phobia, where relationships rarely exceed two years, partly to the trauma of losing his sister.
  • Summary: Kroll’s longest relationships prior to reality TV capped out at about two years, often ending when the relationship reached the ‘get married or break’ point. He admits that his therapist links his commitment issues to his sister’s passing, though he is hesitant to fully blame past poor behavior on that trauma. Kroll prefers being in a relationship because he likes the focused person he becomes, contrasting with the distraction he faces when single.
The Impact of Reality TV on Dating
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(00:18:47)
  • Key Takeaway: Being on Southern Charm accelerates relationship timelines by forcing immediate answers on commitment, such as moving in or proposing, which Kroll feels is unfair to partners.
  • Summary: Kroll believes that reality television speeds up relationship progression by about ten months because producers demand immediate answers regarding dating status and future plans. This pressure forced him to have difficult conversations about moving in with his most recent girlfriend, potentially causing her to uproot her life prematurely. He notes that the need for an immediate ‘arc’ prevents the use of non-committal answers like ‘I don’t know.’
Friendship Dynamics with Craig and Shep
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(00:26:54)
  • Key Takeaway: Kroll views his friendship with Craig Conover as a ‘Spider-Man meme’ where they both point fingers, but he was deeply hurt when Craig used a sensitive accusation against him when pressured.
  • Summary: Kroll confirms that the fights seen on camera are real because men often suppress issues until filming forces them to confront them, noting he is a ‘master Craig button pusher.’ He was particularly wounded when Craig used a rumor about cheating, which Kroll believes was based on something Shep Rose shared, against him, demonstrating a lack of true friendship in that moment. Kroll believes Shep also acted carelessly by sharing sensitive information with Craig, knowing Craig would weaponize it.
Friendship Expectations and Imbalance
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(00:38:37)
  • Key Takeaway: Kroll questions Craig Conover’s commitment to their friendship, feeling Craig misrepresents Kroll’s expectations by suggesting Kroll demands they party like they are in college.
  • Summary: Kroll feels Craig misses the mark in their friendship, especially regarding Kroll’s shift to a more settled lifestyle while dating, which Craig seemed to misinterpret as Kroll wanting him to stop partying. Kroll notes that while he and Craig are deep in some ways, Craig showed little interest in his recent relationship, leading to a lack of necessary communication. Kroll believes that while he and Shep are uncalculated, Shep needs to fundamentally change his long-term single mentality if he ever hopes to settle down successfully.
Transitioning to Relationship Behavior
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(01:00:41)
  • Key Takeaway: Committing to a relationship requires consciously changing long-held single behaviors, including checking in with a partner about comfort levels.
  • Summary: Austen Kroll described needing to move differently and check in with his partner when he started dating Nellie after being single for a decade. He noted that this shift was necessary because he was used to doing whatever he wanted when he wanted. This transition requires a ‘runway’ period when moving toward a committed boyfriend/girlfriend status.
Shep, Taylor, and Online Drama
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(01:02:22)
  • Key Takeaway: Taylor was significantly affected by negative internet commentary following her relationship issues with Shep, which contributed to her spiral.
  • Summary: Austen Kroll expressed high regard for Taylor and suggested Shep ‘did a number on her’ by exposing her to a new world at a young age. He believes the internet heavily impacted Taylor, causing her to show sides of herself she was unused to. The recent online back-and-forth between Sally and Taylor is suggested to have stemmed from past season tensions regarding dating each other’s exes.
Catherine Dennis Communication Issues
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(01:06:31)
  • Key Takeaway: Austen Kroll chose not to engage with Catherine Dennis’s recent negative online posts about him and Craig’s wedding venue due to confusion and past communication history.
  • Summary: Austen Kroll has not spoken to Catherine Dennis since her recent DUI arrest. He was confused by her posting nasty comments about him and Craig’s shared wedding venue after two years of no contact. He opted to let the situation fade rather than respond, despite feeling conflicted about whether to reach out.
Shep’s Feelings for Taylor
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(01:07:49)
  • Key Takeaway: Austen Kroll believes Shep genuinely regrets how his relationship with Taylor ended and considers her ’the one who got away.'
  • Summary: Austen Kroll and Craig analyzed Shep’s intense reaction to his brief dating experience with Sienna, suggesting Shep rushed into it because he missed what he had with Taylor. Austen confirmed that Shep knows he screwed up their relationship. He concluded that Shep likely views Taylor as the one who got away.
Friendship with Craig and Sally Status
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(01:10:56)
  • Key Takeaway: Austen Kroll is currently questioning the long-term durability of his friendship with Craig due to repeated unresolved conflicts.
  • Summary: Austen Kroll admitted he is questioning whether his friendship with Craig is built to last, feeling like he is ‘banging his head against the wall’ in their dynamic. He noted that Craig’s behavior this year has led him to question if Craig truly values their friendship. Regarding Sally, Austen confirmed they have become close friends and she is texting him, but they are not dating.