The Viall Files — Ep. E1041 Ask Nick: “My Best Friend’s Son Is Evil” (December 1, 2025)

Episode Overview

In this “Ask Nick” episode, Nick Viall and the Household (including Natalie Joy and the regular co-hosts) offer candid, nuanced advice to three callers grappling with complex relationship dilemmas. The topics ranged from parenting boundaries and difficult friendships, to relationship satisfaction and prioritizing needs, to navigating the emotional toll of unsupportive in-laws. Nick’s tone is characteristic—warm but unflinching, direct, and full of real-life perspective—while the callers receive both tough love and actionable strategies. Enjoyable for its mix of humor, empathetic insight, and practical communication coaching.

Call #1: “My Best Friend’s Son Is Evil” (Ella, 31)

[01:53–26:01]

Situation:

Ella, a teacher with a Master's in early childhood education, worries about her 3-year-old’s safety around her close friend’s 6-year-old son. The older boy repeatedly hurts Ella’s son without remorse, and Ella feels her friend dismisses concerns instead of setting boundaries.

Key Discussion Points:

• Pattern of Roughness and Lack of Empathy:
  • Ella: “My son's always getting hurt with him... He seems to have no empathy, sympathy, care. Like, doesn't know when to stop. I’m yelling, screaming... he won’t say sorry.” [02:58]
  • Example: The 6-year-old threw a crushed beer can at the 3-year-old’s face, causing a cut [08:05].
• Friend’s Response:
  • Dismisses behavior: “He’s cooped up in the house all day... mad at his sister.” [06:00]
  • Deflects blame: “He told me that it’s because your son was annoying him.” [06:23]
• Boundary Set—Text Message Fallout:
  • Ella eventually texts, saying the boys shouldn’t be together; her partner thinks the text overshared and “did too much.” [09:01]

Advice from Nick:

• Parenting Perspective:
  • Nick reflects on empathy in young children and agrees that by 6, “you know right and wrong.” [04:00]
• Communication Tips:
  • “Never send three paragraphs in a text... It’s literally triggering for most people, certainly for me, extra triggering for someone expecting bad news.” [10:04]
  • “She only read, ‘I don’t want your kid hanging out with my kid.’ That’s all she read.” [10:51]
  • “When you're in conflict... it’s not doing you any good to start by letting them know you have more authority... it’s condescending at best.” [13:27]

Empathy for Both Sides:

• Nick encourages Ella to recognize the sensitivity:
  • “As a parent, you’re not going to allow your kid to hang out with this kid. So your kid’s safe... Now you want to preserve the friendship.” [16:24]
• On criticism:
  • “You want to not be condescending... How do you wish you’d have communicated that better?” [14:26]

Solutions & Reflection:

• Adjust Attitude and Approach:
  • Nick urges separating the need for boundaries from the urge to win arguments:
    • “You don't need to lecture your friend about the boundary... If your kid is in an unsafe situation, you just remove him.” [21:36]
  • Advice: Apologize for the text, focus on repairing the relationship, and communicate in person if possible.
    • “Call her up and say, ‘I just wanted to call and apologize. I shouldn't have sent that text.’” [23:54]

Notable Quotes:

• Nick: “Our feelings are valid, but they aren’t more important than anyone else’s.” [11:09]
• “If you really want to get through to your friend, you have to go out of your way to be careful how you say things.” [17:09]

Call #2: “Should I Stop Playing House?” (Katie, 39, almost 40)

[30:21–59:44]

Situation:

Katie is nearly 40 and has lived with her boyfriend (34) for 1.5 years, together for 2. She values the safety and comfort he provides, but worries she’s “settling” due to a lack of excitement and is frustrated by differences in lifestyle—especially her boyfriend’s lack of effort for her birthday and his “stoner” habits. Is she too accommodating, or missing something fundamental?

Key Discussion Points:

• Defining Love and Relationship Security:
  • “This is the first relationship... I have felt that from the jump... very ease of trust.” [31:25]
• Missing ‘The Spark’:
  • “I don’t have that, like, excitement.” [31:56]
  • Nick: “That’s a you problem though, right?” [32:00]
  • Discussed difference between toxic thrill and healthy security.
• Communication and Love Languages:
  • She wants more thoughtful gestures (e.g., on her birthday). Despite telling her boyfriend and even giving a list, he “doesn’t follow through.” [38:01]
  • “He’s always receptive... just not a lot of follow through.” [37:52]
• Lifestyle Fit & Partners as Equals:
  • Katie wishes her boyfriend were more intellectually and emotionally driven, less lazy.
  • “I would like nice, healthy soil for my plant to grow.” [52:30]

Advice from Nick:

• Assessing Needs vs. Pet Peeves:
  • “You aren't quite sure which is which when it comes to your relationships.” [50:03]
  • “Pet peeves versus non-negotiables—I think you need to really figure out what matters.” [55:58]
• Self-Reflection:
  • “Are you a ‘relationship thrill seeker’—do you mistake instability for excitement?” [36:47]
• Prioritizing What Matters:
  • “I value being a team... What’s most important to you, and what can you get elsewhere?” [44:22]
• On Making Decisions:
  • “It shouldn’t take you that long to figure out if someone is your intellectual equal. You should know that by now.” [53:20]
• Brutal Honesty:
  • “You’re focused on what you’re not getting out of the relationship. I... am constantly reminding myself that my wife meets my non-negotiables.” [56:11]

Notable Quotes:

• Nick: “Your uncertainty comes from your lack of conviction about what matters to you.” [55:58]
• Katie: “I think it’s just a difference of lifestyle. I don’t love the way he spends his downtime.” [50:26]
• Nick: "Until you learn how to change that, you’re never going to be happy because you’ll always find something about your partner that annoys the fuck out of you." [51:57]

Call #3: Difficult In-Laws and Emotional Boundaries (Kate, 30)

[64:02–96:49]

Situation:

Kate, recently engaged, faces problems with her fiancé’s emotionally and financially dependent parents. While initially she admired his loyalty, it’s become a source of exhaustion and stress, especially as she wrestles with where she fits in and how to set boundaries.

Key Discussion Points:

• Financial Entanglements:
  • Fiancé pays parents’ mortgage and provides ongoing support due to their poor financial decisions. [65:46]
  • Kate’s concern is more about the future (“sending kids to college” etc.) than present restrictions.
• Emotional Manipulation & Drama:
  • Parents are “so exhausting to be around,” constantly fighting, and rely on their kids even for basic transportation. [68:34]
  • Kate recounts uncomfortable and often toxic moments, including public fighting, body-shaming, and guilt trips.
• Communication Breakdown:
  • Fiancé shuts down conversations (“Please do not talk to me about this. I am exhausted by this situation.”) [73:56]
  • Kate feels excluded and “villainized” at times, and has learned to keep quiet to avoid being targeted. [77:18]

Advice from Nick:

• Pick Your Battles and Lead with Empathy:
  • “Be careful how you handle that and not make it worse... There’s a fine line between being helpful and making things a you problem.” [71:09–72:09]
• On Financial Boundaries:
  • “Can he afford it? You came into a situation that already existed.” [71:09]
• Setting Emotional Boundaries & Inclusion:
  • “You need to feel like you and your fiancé are on the same page.” [79:48]
  • “He can’t make you feel shut out... You have the right to just have a conversation with your fiancé—to try to get on the same page when it comes to something that’s constantly causing some emotional instability.” [83:40–83:51]
• Tough but Fair:
  • “You have to remain calm and just point out that’s not a solution to this problem. And you can’t make me feel shut out.” [96:23]

Strategies Suggested:

• Use “us/we” language; aim to be his ally, not his critic.
• Establish regular, non-triggered debriefs to discuss parental issues.
• Demand inclusion and mutual support, but recognize which fights are worth picking.

Notable Quotes:

• Nick: “Start with: How can I support you?... What you don’t want to do is come from a place of bitching about his parents.” [95:24]
• “You’re empathizing with his situation—make him feel like you’re his cheerleader.” [91:21]

Memorable Moments & Quotes

• On Parent Conflict:
  Nick: “Never send three paragraphs in a text, ever. It’s literally triggering.” [10:04]
• On Relationship Security:
  Nick: “Are you a dating thrill-seeker? That would be a you problem.” [36:47]
• On Picking Pet Peeves vs. Non-negotiables:
  Nick: “You’re making a decision to focus more on what you’re not getting—until you learn to accept certain things, you’ll never be happy.” [51:57]
• Balancing Empathy and Assertiveness:
  “You need to feel like you’re his top priority... but you can’t expect me to always just be okay with that.” [84:51]
• On In-Law Drama:
  “Channel your hate into pity.” [82:26]

Key Takeaways

• Protecting your child is never wrong, but communication and tone matter, especially among close friends.
• Know the difference between “pet peeves” and “non-negotiables” in relationships; don’t confuse discomfort with incompatibility.
• Unaddressed baggage and lack of boundaries—especially with parents—will eventually spill over into romantic relationships.
• Take stock of what’s most important and communicate in a way that makes your partner feel like you’re working as a team.

Timestamps for Featured Calls

• [01:53] — Call 1: Parenting Boundaries and Friendship Fallout (Ella)
• [30:21] — Call 2: Is Safety Enough? Seeking Relationship Thrill (Katie)
• [64:02] — Call 3: Setting Boundaries with Overbearing In-Laws (Kate)

This episode exemplifies The Viall Files’ signature blend: real talk, actionable advice, and empathetic, sometimes tough, coaching. The calls offer relatable dilemmas for any listener navigating boundaries—whether with friends, romantic partners, or family.