The Viall Files

Episode E1022: Ask Nick – I’m Sleeping with an Engaged Man
Date: October 27, 2025
Host: Nick Viall
Guests/Callers: Amber, Lexi, Seth & Emma

Episode Overview

This “Ask Nick” episode of The Viall Files tackles raw, challenging relationship dilemmas submitted by listeners. Nick Viall, joined by household regulars, fields confessions and quandaries that involve infidelity and self-forgiveness, family wedding drama, and the complex negotiations of trust within addiction and non-monogamy. With a tone of tough love punctuated by empathy and self-reflection, Nick gives actionable, sometimes sobering advice aimed at fostering genuine growth and accountability.

Key Discussion Points

1. “I’m Sleeping with an Engaged Man” – Amber’s Story

(02:27-27:47)

The Situation

• Amber, 27, has been involved in a five-year situationship with a man who is now engaged.
• She acknowledges that he's been cheating on his fiancée with her and that she has justified this to herself because of her longstanding feelings and connection.
• Amber found out about his engagement only after he tried to hide it by blocking her on social media.

Advice and Insights

• Self-Justification and Responsibility:
  • Nick urges Amber to deeply reflect on how she’s been able to rationalize “doing a shitty thing," noting everyone's capacity to justify poor behavior even when they know it’s wrong.
    • Quote: “Good people who do bad things, which is all the time, every day, it’s not because they’re evil. It’s because they’re able to justify it.” (05:09)
• Forgiveness vs. Accountability:
  • Amber grapples with regret and whether she deserves happiness or a "happy ending” after this. Nick encourages owning her choices and not wallowing in self-pity as a means of self-improvement.
    • Quote: “Acknowledge the mistakes you’ve made, both in terms of how you’ve treated yourself so poorly and how your weakness caused you to do something shitty to another person.” (14:37)
  • Nick notes that while Amber's actions were wrong, the primary accountability lies with the man who has deceived both Amber and his fiancée.
• Self-Worth and Boundaries:
  • Nick zeroes in on Amber’s low self-esteem and willingness to settle for “crumbs” as a root for her choices.
    • Quote: “You thought so little of yourself that you accepted crumbs from this man. You had no standards, not even to do the right thing.” (10:07)
  • He recommends therapy and deliberate self-investment, highlighting the importance of acknowledging personal achievements and building confidence.
• Break Free and Move Forward:
  • Nick pushes Amber to fully sever ties, including blocking the man on all platforms—even quitting their fantasy football league if necessary.
    • Quote: “For $100, you were selling yourself out at the risk of staying in his world so that he can emotionally fuck with you from time to time... You gotta stop making excuses for your poor choices in life.” (19:42)
• No Contact/No Closure Needed:
  • Nick warns against contacting the fiancée, stating it would be out of spite rather than to help, and is glad Amber is not considering it.
• Empowerment:
  • The emphasis is on elevating standards and practical steps to distance oneself to avoid repeating the same patterns.
    • Quote: “You gotta stop yourself and catch yourself and call yourself out. Stop making excuses about why you can’t move on.” (20:27)

Notable Quotes

• Amber: “I have a lot of regret now and kind of feel like I almost don’t deserve, like, a happy ending after this moving forward.” (06:09)
• Nick: "If anything, get mad at yourself for a period of time and stop treating yourself so shitty, you know, like you have been." (11:06)
• Nick: “Give yourself a little bit of grace. This is gonna take some time for you to heal, but... you gotta hold yourself to a higher standard.” (21:34)

2. “My Mom Is Getting Married At the Same Time as Me” – Lexi’s Dilemma

(31:48-44:46)

The Situation

• Lexi is a 26-year-old bride-to-be whose mother became engaged around the same time as her and is pushing to get married just weeks before Lexi’s wedding.
• The overlap has led to shared experiences—like joint wedding dress shopping—that Lexi finds uncomfortable and emotionally fraught.

Advice and Insights

• Setting Boundaries Compassionately:
  • Nick advises avoiding judgmental language, recommending that Lexi not describe her mom’s actions as “weird” when expressing concern; framing and wording matter, especially when discussing sensitive family issues.
    • Quote: “Weird is such a judgmental word... when you’re using that to describe how you’re feeling about someone else’s actions, it’s going to really be upsetting to them.” (35:18)
  • He suggests affirming her support for her mom’s happiness, but clearly requesting the separation of wedding plans so both experiences remain special and distinct.
• Empathy and Practicality:
  • Nick encourages Lexi to consider her mother’s sensitivities and potential desire for validation.
  • He normalizes Lexi’s desire for her own moment, but also challenges her to assess what the overlap is truly costing her—often, principle vs. peace.
• Collaborative Planning and Direct Conversation:
  • Nick recommends a candid conversation focused on logistics, support, and mutual validation—reminding Lexi to apologize for her earlier choice of words and set boundaries without accusation.
    • Quote: “Can we just separate the two going forward?... I don’t want to have, like, a joint wedding thing, you know?” (44:11)

Notable Quotes

• Nick: “If it doesn’t cost you much to give your mom, you know, some validation that she clearly needs... it just might make your life a hell of a lot easier.” (42:46)
• Lexi: “[My mom] got engaged like two years ago the same day my dad got married.” (38:24)

3. Addiction, Betrayal, and Trust in Marriage – Seth & Emma

(47:37-98:46)

The Situation

• Seth and Emma, together 13 years with a young daughter, wrestle with a confluence of betrayals: Seth’s marijuana addiction, racking up $50K+ in hidden debt, and a major breach of trust during ethical non-monogamy (Seth contracted HPV and gave it to Emma by breaking agreed sexual boundaries).
• Emma struggles between wanting to protect her family and feeling forced into the role of “enforcer” in their marriage, giving ultimatums as trust erodes.

Advice and Insights

• Addiction and Self-Awareness:
  • Seth admits to having used marijuana habitually as a means of escape, recognizing it had become an addiction, especially after Emma presented a “me or the weed” ultimatum.
    • Quote (Seth): “For me, I think it was... I was consuming it whenever I could or whenever there was an opportune moment. I wasn’t even, like, actually getting high anymore.” (56:37)
• Deeper Patterns of Dishonesty:
  • Nick detects a larger pattern of Seth prioritizing his own gratification, then hiding it under the guise of not wanting to upset Emma—a sophisticated but ultimately selfish rationalization.
    • Quote: “Your default is to do what you want and then lie about it because you’re trying to not upset her, which is ultimately... not sustainable.” (64:48)
• Safety and Emotional Security:
  • Nick pinpoints Emma’s central dilemma: she no longer feels emotionally or physically safe due to Seth’s betrayals and financial secrets; the issue is not marijuana per se, but systemic dishonesty.
    • Quote: “If Emma constantly has to wonder if she can trust you, Seth, it is no fun feeling you have to play watchdog or cop or detective with your own spouse.” (64:48)
    • Quote: “There are things Seth is doing that is making you feel objectively unsafe in this relationship... your problem isn’t what Seth’s willing to do. Your problem is when Seth wants to do something in the moment, he wants to do it.” (67:00)
• Compartmentalization Doesn’t Work:
  • Nick challenges Seth’s view that trust can be siloed; if he’s dishonest in one area, he cannot expect Emma to trust him in others.
    • Quote: “You can’t feel safe in one category of your life and not feel safe in another. It’s like, ‘Well, I only lie to her about money, so she shouldn’t be worried about me lying to her about sex.’ I don’t think the human brain works that way.” (74:44)
• Addiction and Comparisons:
  • Seth identifies dissatisfaction—envy of others’ financial status in Silicon Valley—as a driver for his reckless behavior. Nick points out that such ego-driven comparison will persist even if circumstances change.
    • Quote: “A lot of what you’re describing, Seth, as this like ego driven insecurities or thoughts... tomorrow you woke up and your financial earning increased tenfold, you would still be able to compare yourself to people and feel less than.” (91:52)
• What It Means to Show Up:
  • Nick pushes Seth to internalize that being a good husband and father is about reliability, honesty, and prioritizing family above personal impulses.
    • Quote: “The whole joy of being a husband and as a father is you have the opportunity to wake up every day and get something out of thinking of other people before thinking of yourself. It costs you nothing other than selflessness.” (93:52)
• Healing and Moving Forward:
  • The couple is encouraged to continue therapy, but above all, Seth must demonstrate that Emma and their daughter come first—through transparency, not avoidance.
    • Quote (Nick, to Seth): “You have to be willing to recognize that in those moments where you want to have your cake and eat it, too, you have to be willing to, like, check yourself and communicate with your wife... That is very much the opposite of dad and husband energy.” (95:24)

Notable Quotes

• Emma: “It feels like my husband is constantly seeking some sort of, like, high or, like, something impulsive, whether it’s shopping or sex or getting high or something like that.” (59:32)
• Nick: “If she has to wonder and any, in any type of regularity whether you’re being honest with her about some very consequential things, it’s hard to feel safe in those situations.” (83:24)

Noteworthy Moments & Timestamps

| Time | Segment/Quote/Event | |---------|-----------------------------------------------------------------------------| | 03:10 | Nick: “I think it’s important for you to understand why you’ve been able to justify it.” (to Amber) | | 10:07 | Nick: “Honestly, you gotta raise your standards for yourself.” | | 19:42 | Nick: “For $100, you were selling yourself out at the risk of staying in his world…” | | 35:18 | Nick (to Lexi): “Weird is such a judgmental word…” | | 44:11 | Nick’s role-play of how Lexi can ask for wedding planning boundaries | | 56:37 | Seth: “I was using marijuana as though I was a rock star… I wasn’t even getting high anymore.” | | 64:48 | Nick (to Seth): “Your default is to do what you want and then lie about it…” | | 74:44 | Nick: “You can’t feel safe in one category of your life and not feel safe in another.”| | 83:24 | Nick: “If she has to wonder and any… whether you’re being honest…, it’s hard to feel safe in those situations.”| | 91:52 | Nick: “Tomorrow you woke up and your financial earning increased tenfold, you would still be able to compare yourself to people and feel less than.” |

Tone and Takeaways

The tone throughout is direct but compassionate, blending tough love, practical advice, and empathy. Nick is unflinching about difficult truths, especially around self-deception, boundaries, and what it means to treat oneself and loved ones with honor. Listeners are reminded that real growth comes from accountability, from owning mistakes—but that self-forgiveness and future standards matter more than past errors. Ultimately, the message is to stop making excuses, do the hard work of healing, and set and maintain boundaries that reflect your worth.

Conclusion

This episode of The Viall Files offers a candid look at the challenging underbelly of love and commitment, with heartfelt listener calls about cheating, challenging mothers, and marriage on the brink. Nick Viall’s signature mix of humor, tough love, and sagely lived-in advice makes it both a wake-up call and a practical toolkit for anyone seeking clarity and self-respect in their relationships.