The Viall Files, E1003: "Ask Nick - Cheating in an Open Relationship"

Date: September 22, 2025
Host: Nick Viall
Guests: Callers: Catherine, Jessica, Kelly

Overview

In this episode of "Ask Nick," Nick Viall, with frequent interjections from Natalie Joy and other members of "the Household," tackles three listener relationship dilemmas:

1. Repairing and setting boundaries with an emotionally abusive mother
2. Navigating a painful broken engagement over a contentious prenup negotiation
3. Supporting a pregnant friend in a polyamorous marriage with boundary and trust issues

Nick delivers tough love, empathy, and solid advice, especially focusing on self-esteem, boundaries, and communication. The overarching themes are about claiming your power in relationships, learning to set and enforce boundaries, and supporting others without overstepping.

Call 1: Catherine – Setting Boundaries with an Emotionally Abusive Mother

Starts: [03:14]

Background

• Catherine (31) is a stay-at-home mom with two young children and a supportive husband.
• She struggles with doubts about her parenting, stemming from a lifetime of emotional abuse and belittlement by her mother.
• Relationship with her mother improved during pregnancy but broke down after a visit to her mother’s home.
• Catherine’s mother has a pattern of bullying, invalidation, and damaging statements (e.g., “I love you, but I don’t like you”).
• Catherine seeks advice on moving forward, letting go of guilt, and whether to continue reaching out.

Key Discussion Points & Insights

• Validation of Parenting:
  Nick reassures Catherine her doubts about being a good mother actually reflect her commitment.
  Nick: “The fact that you have speaks volumes about your capabilities as a mother and your intentions to be a mother.” [13:57]

• Emotional Damage & Boundaries:
  Nick bluntly labels her mother a bully who will only respond to clear boundaries, not apologies or attempts to please.
  Nick: “There’s only one way to deal with bullies, and that is to stand up to them.” [09:48]

• Power Dynamics:
  Nick urges Catherine to recognize she now has the power and agency to set terms for the relationship.
  Nick: “You have all the power in this situation. And so far you are acting as if your mom still has all the power.” [29:20]

• Prioritizing Relationships:
  Higher priority should be given to Catherine’s husband and children, not to appeasing her mother.
  “Your in-laws and your mom…they don’t really matter when it comes to your children’s life...because they have you.” [32:23]

• Concrete Advice:

  • Stop seeking validation from her mother.
  • Invest energy in brother and nuclear family.
  • Use letters/journaling for self-affirmation instead of seeking reconciliation.
  • Allow her husband to be an ally and enforce boundaries as a team.
  • Cut or strictly limit contact with the mother if boundaries are repeatedly violated.

Notable Moments

• On Apologizing to Bullies:
  Nick: “Your mom doesn't see an apology as ownership...she just sees an apology as weakness.” [19:08]
• Parental Priorities:
  Nick: “Your family...is your husband and your kids. And everyone else is just lucky to have a seat at the table that they're not entitled to.” [44:23]
• Self-Affirmation:
  Nick: “Stop writing letters to mom like you write a letter to yourself.” [33:25]

Call 2: Jessica – Breaking off an Engagement over a Prenup

Starts: [47:36]

Background

• Jessica (32) broke off an engagement because she and her fiancé couldn’t agree on a prenup.
• The fiancé, a dentist, wanted to protect current and future earnings/assets, and had strong notions about marriage partnership (including expecting Jessica to be a stay-at-home mother).
• Both hired lawyers; negotiations broke down over fairness, spousal support, childcare, and fears of financial vulnerability.

Key Discussion Points & Insights

• Reality of Marriage and Prenups:

  • Nick demystifies prenups: "Everyone who gets married has a prenup, it’s just whatever the state says if you don’t do one yourself." [54:40]
  • It's pragmatic (not unromantic) to want a prenup.

• Negotiation Breakdown:

  • The fiancé wanted to keep all current and future earnings separate, including investments/businesses acquired during the marriage.
  • Jessica was open to a prenup in principle but worried about giving up her career and financial security.
  • Attempts to compromise — e.g., being paid her salary to be a stay-at-home mom, shared childcare — failed.
  • Neither felt protected or fairly treated by the other's terms.

• Why Negotiations Failed:

  • Nick sees both parties as trying to "win" or protect themselves rather than each other.
  • Successful prenup negotiation requires mutual empathy: "You both should try to want to make...the prenup if you were the other person." [85:04]
  • Both sides ended up seeing what the other would be like in a divorce ("uncompromising and only worrying about themselves").
  • Lack of pre-negotiation affirmation (reminding each other of their partnership/love) made process transactional and adversarial.

• Moving Forward:

  • Jessica asks how couples successfully negotiate; Nick emphasizes communication, empathy, and willingness to compromise.
  • Calls for Jessica to assess her own role and not just blame the ex-fiancé.
  • Suggests a willingness to revisit the breakup, owning up to mistakes if so inclined.

Notable Quotes

• On State Laws & Prenups:
  Nick: "The idea that some people have out there, ‘I would never sign a prenup’ is delusional...you're literally signing a prenup the moment you sign a marriage license." [54:40]
• On Compromise:
  Nick: "No one should feel like they won. If one person's like, ‘whew, great,’ then that was not a very good starting point to a marriage." [76:59]
• On Blame and Learning:
  Nick: “If I'm you, this is the type of person who...this would be a moment to take my ego out of it, take my pride out of it, ask myself, ‘Did I do everything I could?’” [103:59]

Call 3: Kelly – Supporting a Pregnant Polyamorous Friend with Boundary Issues

Starts: [115:58]

Background

• Kelly’s friend is pregnant in a polyamorous marriage, but the husband's repeated boundary-crossing and dishonesty (cheating even prior to opening the relationship, hiding relationships, manipulations) concern her.
• The friend is not the principal driver of polyamory, and while she does date others, she's struggled with her husband's disregard for boundaries.
• Kelly and other friends are worried about the support her friend will receive postpartum, fearing for the friend's wellbeing and emotional health.

Key Discussion Points & Insights

• The Limits of Friendship:

  • Nick cautions that Kelly’s urge to intervene is understandable but can overstep, especially given much of her information comes secondhand via the “friend group gossip mill.”
  • Nick: "You can't save people who don't want to be saved, and you can't help people who aren't asking for your help." [132:21]

• Supporting vs. Judging:

  • Nick acknowledges it's hard to understand or avoid judging an unconventional relationship, but what matters is being available and validating, not policing.
  • Nick: "If someone's not being seen, you see them. It's not saying, ‘Hey, you should be with someone who sees you.’ She’s an adult...in therapy..." [126:41]
  • Don’t insert “what you’ve heard” — it’ll come across as gossipy or invasive.

• Concrete Advice:

  • Regularly check on her friend, offer emotional support, ask non-judgmentally about how she's doing and whether she's getting what she needs.
  • Avoid attempting to confront, rescue, or draw conclusions unless the friend actually reaches out for help or advice.
  • If/when the friend brings up concerns, validate and support, but don't push her toward a particular action.
  • In a group where no one else is polyamorous, avoid group judgment or gossip tone.

• Setting Intentions:

  • Nick notes it’s okay to have strong maternal/protective instincts, but emphasizes, “...the fact that she is pregnant, you causing your friend a lot of stress would be the literal opposite of protecting that baby.” [133:01]

• Final Word on Support:

  • Be a supportive friend, stay in your lane, and only step in deeper if her friend explicitly asks.
  • Kelly (accepting): “Be a supportive friend. Stay in your lane. Got it.” [139:00]

Memorable Quotes & Moments

• Nick's affirmation for struggling parents:
  “Your desire to be the mother you want to be is going to make you a great mother.” [13:57]

• On power in adult relationships:
  “You have all the power in this situation. And so far you are acting as if your mom still has all the power. The parent-child relationship is very difficult to break. Right. Because 18 years of your life...your mom had literally all the power.” [29:20]

• On prenup negotiation as a stress test for marriage:
  “What you guys showed a glimpse of is how you guys would be in this divorce, which is both kind of really stubborn and only thinking of yourselves.” [78:37]

• On the wrong way to negotiate a prenup:
  “The baseline for both of you was guaranteeing being yourself, that you were going to be in the best possible situation even if you got divorced.” [81:31]

• On helping friends with unconventional relationships:
  “If someone's not being seen, you see them...but don't say, 'You should be with someone who sees you.' She's an adult.” [126:41]

Timestamps for Important Segments

• [03:14] Call 1: Catherine – Mother/daughter dynamics, boundaries, self-worth
• [47:36] Call 2: Jessica – Prenup negotiation, relationship dissolution
• [115:58] Call 3: Kelly – Polyamorous relationship, supporting a friend, boundaries

Episode Tone & Takeaways

• Nick is empathetic but firm, supportive while pushing tough truths (“You’re wasting too much energy on this woman”), and balances pragmatism with humanity.
• There's frequent meta-advice on seeing things from the other's perspective, claiming your agency, and not trying to "win" at the expense of connection.
• Highly relevant for listeners navigating complicated family dynamics, the realities of merging finances/marriage, and the boundaries of friend intervention in difficult relationships.

Bottom Line:
Whether grappling with toxic parents, high-stakes prenup talks, or watching a friend in an unusual and fraught relationship, Nick’s guidance centers on reclaiming personal power, honest self-reflection, conscious boundary-setting, and the importance of empathy — both for others and oneself.