VIEWS with David Dobrik & Jason Nash – Episode: Dating a Billionaire (June 19, 2025)

In this engaging episode of VIEWS with David Dobrik & Jason Nash, the dynamic hosts delve into the complexities of high-profile relationships, brand deals, and the unique challenges that come with significant wealth. Joined by friends like Ilya Fedorovich and Natalie Mariduena, and featuring a special story from Naveen, the conversation offers a candid look into navigating life when dating someone extraordinarily wealthy.

1. Airline Travel Woes: A Comedy of Errors

The episode opens with David recounting a chaotic travel experience that underscores the unpredictable nature of airline operations.

• Delayed Flights and Booking Confusion (00:17 - 03:09): David shares his frustrating ordeal with American Airlines, where miscommunication led to him being mistakenly booked on a delayed flight from the previous day. This mix-up caused him considerable stress, highlighted by his humorous frustration:

  David Dobrik [01:09]: "I think that's really weird...You couldn't be more confused with this entire situation."

• Unexpected Airline Issues (03:09 - 04:12): The discussion shifts to a bizarre news story about an India flight that crashed shortly after takeoff, sparing only one passenger under mysterious circumstances. This segment adds a layer of seriousness amidst the humor:

  Ilya Fedorovich [03:10]: "It's fucking insane."

2. Brand Deals and Spending Habits: Balancing Money and Relationships

Jason Nash introduces the topic of securing brand deals and the ensuing dynamics it creates within personal relationships.

• Securing Lucrative Deals (06:05 - 07:13): Jason excitedly shares his experience landing a $85,000 Instagram story deal, juxtaposed against David’s mock frustration over the perceived triviality of brand promotions:

  Jason Nash [06:09]: "Want to pay you $85,000. One Instagram story."

• Managing Brand Deals at Home (07:13 - 15:18): The conversation humorously explores how brand deals impact household spending, particularly focusing on Naveen's shopping spree at Gelson's and the strain it places on Jason:

  Jason Nash [07:20]: "It's a lot of work...I can't celebrate victories."

3. Navigating Relationships: Insights from Dating a Billionaire

Naveen shares her personal story about dating a wealthy individual, shedding light on the challenges and control that can come with such relationships.

• Naveen’s Story: The Price of Wealth (16:30 - 25:00): Naveen narrates her experience with a billionaire who financially supported her but exerted excessive control over her life, including monitoring her phone and restricting her activities:

  Naveen [22:39]: "I couldn't leave the house...he would make me bike ride a lot."

• Impact on Personal Freedom (25:00 - 28:34): The hosts discuss the emotional and psychological toll of being in a relationship where money becomes a tool for control, highlighting the importance of personal freedom and autonomy.

4. Special Treatment and Celebrity Encounters: The Double-Edged Sword

David shares stories that illustrate the perils of fame and the often unwanted special treatment that accompanies it.

• Encounter with CeeLo Green (37:58 - 38:44): David describes a tense interaction with the artist CeeLo Green at the airport, emphasizing the frustrations of dealing with celebrities who expect special privileges:

  David Dobrik [37:58]: "He was really trying to get this bag through TSA and they weren't really letting him."

• Mixed Feelings About Special Treatment (38:45 - 40:25): The hosts debate the fairness and discomfort that come with special treatment, especially in public settings like airports and theme parks:

  David Dobrik [40:13]: "I have to bury my head in shame...It's just fucked up."

5. Personal Anecdotes and Group Dynamics: Friendship and Financial Management

The conversation shifts to personal interactions among friends, focusing on financial habits and the humorous side of managing money within friendships.

• Discussing Spending Habits (41:00 - 43:54): The group shares funny stories about budgeting, tipping discrepancies, and the challenges of aligning spending habits with partners:

  Natalie Mariduena [43:29]: "I thought lunch would be like $80."

• Balancing Friendships and Finances (44:14 - 47:56): Jason and John discuss the nuances of brand deals and spending, highlighting the sometimes absurd lengths influencers go to monetize their personal lives:

  Jason Nash [44:23]: "Complete scam."

6. Ethical Considerations and Emotional Boundaries: Moving Forward After Loss

A poignant segment addresses how individuals cope with the loss of a partner and the ethical implications of moving on emotionally and romantically.

• Debating the Right Time to Move On (45:03 - 48:47): The hosts engage in a heartfelt debate about how long one should wait to date or pursue new relationships after the death of a partner. Julia’s and John’s responses spark a deep conversation on respecting emotional boundaries:

  Julia [46:06]: "Two years." Jason Nash [46:17]: "Two years... a long time over."

Conclusion

The episode wraps up with the hosts reflecting on the importance of authenticity and maintaining personal boundaries amidst fame, wealth, and the complexities of modern relationships. David humorously hints at returning from France, promising more insightful and entertaining conversations in future episodes:

David Dobrik [48:52]: "So if you find him, I commend you. Go check out Jason's podcast, All Good Things, and I'll see you guys when I get back from France."

Notable Quotes:

• David Dobrik [01:09]: "I think that's really weird...You couldn't be more confused with this entire situation."
• Naveen [22:39]: "I couldn't leave the house...he would make me bike ride a lot."
• Jason Nash [44:23]: "Complete scam."
• Julia [46:07]: "Two years."

This episode of VIEWS offers a blend of humor, personal stories, and thoughtful discussions, providing listeners with a window into the intricate dance of managing relationships and finances in the spotlight.