The Viall Files – Episode E999: Ask Nick – Cheating Parents

Date: September 15, 2025
Host: Nick Viall
Guests/Callers: Natalie Joy, Blair, Sydney, Margaret

Episode Overview

In this "Ask Nick" episode, Nick Viall and co-hosts dive into relationship dilemmas brought forward by listeners. From questioning longtime "friends with benefits" to navigating commitment issues and unpacking the impact of parental infidelity and secrets, Nick offers blunt, practical advice with his characteristic empathy and humor. This week centers on how complicated family backgrounds, trust issues, and communication struggles shape our ability to form and sustain healthy romantic relationships.

Caller 1: Blair – Should I Confess My Feelings to a 15-Year “Buddy”?

Segment start: [01:01]

Summary

Blair, 31, has had an on-and-off emotional and physical relationship with a friend for 15 years. Both have pursued other relationships but keep finding their way back to each other. Blair wonders if she should finally confess her feelings and ask for a real shot at a relationship.

Key Discussion Points

• History & Pattern:
  Blair and her friend have never sustained a relationship but keep reconnecting after breakups. She revealed having told him about her crush a few years back, but it "didn’t count” and wasn’t direct.

• His Side:
  He shares nostalgia-laden compliments, e.g. "When I see you, it feels like time folds in on itself... it just feels natural and normal" ([06:26]), but frames things in the past or as casual.

• Physical Chemistry vs. Relationship Potential:
  Blair is sure of his attraction, but feels intimidated and has trouble being truly vulnerable.

• Nick’s Take:
  Nick urges Blair to be assertive and direct—no more hints or "I have a crush" ambiguity:

  "You have to be direct...it's not about nostalgia. I don't think it's that special what he said to you...he doesn't see you as an option to have a relationship with. He sees you as the girl he has been sleeping with..." ([09:30])

• Strategy for Change:
  Nick explains she must challenge the dynamic:

  "You have to act like he's missing out...You almost have to give him the pitch...Women want to do that even less than men—'I don't want to chase'—but this is a different scenario. You both have mental barriers...I think your pitch is: 'I think we should date. I really care about you. We've known each other our entire adult lives. We always find our way back to each other...'" ([11:18])

• Encouragement for Confidence:
  Nick notes that confidence and boldness are key—maybe even a little edge:

  "At times, men really respond to very confident, aggressive women who know what they want." ([11:57])

  And when things get sentimental:

  "Why does he think he's in a position, being a guy you have slept with your entire adult life off and on, that your future husband would be okay with that?" ([14:50])

• Closure on Timing and Approach:
  Nick recommends an in-person, no-BS conversation, and to prepare for possible rejection:

  "Make your pitch once and leave it at that...If he gives you the 'I don’t know', just be like, 'Well, I think you’re an idiot.' A little childish name-calling can go a long way with men." ([18:30])

• On Self-Respect & Future:
  Nick reminds Blair she's 31 and doesn't want to be casually hooking up with the same guy into her thirties if it isn't going anywhere:

  "If I'm still f***ing this guy at 35...things have gone wrong and I've made decisions not in my best interest." ([22:40])

Notable Quotes

• Nick: "It really is about you being confident in how you feel and that he's blind if he doesn't see what you see." ([27:37])
• Blair: "I will rehearse and use confidence and slight bitchiness. Nothing too crazy, but a little bit." ([28:11])

Caller 2: Sydney – "I Can't Commit to My Non-Boyfriend Boyfriend Because of His Haircut"

Segment start: [31:53]

Summary

Sydney, 24, has been seeing a guy for five months. Their relationship is undefined, primarily due to Sydney's own reservations—partly over his mullet haircut, but also because she's never been in a serious relationship. She wonders whether she should make things official.

Key Discussion Points

• Their Dynamic:
  Started casual, progressed to regular hangouts, trips, meeting friends, and everyday texting—a relationship in all but name.

• Sydney's Internal Battle:
  Worries about missing out on fun, not having enough experience, or introducing him to family with a "mullet story"—“I care about him, but I'm afraid to go all-in.”

• Nick’s Take:
  Nick pokes fun at the superficial concern over his haircut, but challenges Sydney to get real:

  "It's more of an ick that he's a 30-year-old with two roommates than that he has a mullet." ([34:53])

• Labels vs. Intimacy:
  Nick identifies the paradox of dating culture fearing commitment, but notes intimacy and time spent matter more than semantics:

  "After five months...hopefully you've been building a rapport and a comfort level that you didn't have in the first couple weeks of hooking up." ([39:51])

• Learn by Doing:
  Nick advises embracing risk and experience:

  “If you like him, you should try! You can always break up…Even if he f***s you up emotionally and breaks your heart in two years, it might be worth it. That’s a rite of passage.” ([49:12])

• Authenticity in Relationships:
  Nick warns against “professional casual daters” who never learn how to make compromises and only want self-serving connections.

• How to Define It:
  Nick suggests Sydney just declare her intentions instead of asking permission:

  "Honestly, with what I'm hearing, it would make a lot of sense for you...to just be like, by the way, I started telling people you’re my boyfriend and we’re together." ([54:45])

• On Relationship Balance:
  Sydney voices worry about giving up career, friends, or independence; Nick counters:

  “You don’t have to be the couple that is inseparable…you can strike a balance and you just have to talk about expectations.” ([57:42])

• Grow Up and Don't Overthink:
  Nick prods Sydney to mature:

  “This is me, in the nicest possible way, saying: you need to grow up a little bit. And so does he.” ([61:57])

Notable Quotes

• Sydney: "I feel like I gotta put the key into ignition a little bit." ([65:52])
• Nick: "If he rejects your request to define this relationship, then you really need to point out, well, then you're an idiot. You're calling me babe. But fine. You definitely need to shut it down, though." ([64:15])
• Nick: “You can have a boyfriend, you can break up… I would rather be 26 with an ex-boyfriend and that lived experience…” ([66:37])

Caller 3: Margaret – Did My Cheating, Closeted Dad Ruin My Trust?

Segment start: [73:20]

Summary

Margaret, 26, details finding out as a teen that her father was having affairs with men and was secretly gay, but never explicitly came out. Her parents’ marriage ended, her dad remains reticent about his sexuality, and Margaret is left fearing deep relationships and potential betrayal.

Key Discussion Points

• Family Backstory:
  Her father was a strict, resentful presence; her mother was primary caretaker. After discovering evidence and confronting both parents, the family remained emotionally closed-off ("my family doesn’t like to talk about things").

• Dad Never Came Out:
  Margaret is frustrated by her father’s lack of vulnerability and accountability:

  “He’s never really taken accountability, never admitted anything…multiple opportunities to be truthful to me.” ([77:35])

• Complex Feelings:
  Margaret expresses that it’s not the homosexuality, but the secrecy, denial, and years of emotional distance that left scars.

• Nick’s Guidance:
  Nick draws a clear line between her dad’s struggle with sexual identity and his failings as a partner/parent—and the need for immense grace for someone coming out, especially from that generation:

  "When you, like, send evidence... or go to your dad and be like, I know. Are you going to take accountability? That’s like... are you going to take accountability for being gay? ... He's not hearing, 'Hey dad, I love you no matter what.' ...but 'You owe me the truth.'" ([80:59]–[86:12])

• On Letting Go:
  Nick repeatedly encourages Margaret to differentiate between wanting to be right/validated and actually cultivating happiness or closeness:

  “...being close with your dad might require you to accept certain things and give yourself whatever closure you need without necessarily getting it from your dad.” ([90:16]) "Sometimes you have to let shit go, you know, like, sometimes you have to accept that people feel differently than you... Do you want to be right, or do you want to be happy? And you have a lot of 'I want to be right' energy." ([106:32])

• Relationships & Trigger Points:
  Margaret worries her history makes her “hypervigilant” about betrayal in relationships and sometimes “looks for connection as to why I’m not sure.” She notices a pattern where she sets high expectations for how partners should support her, and is triggered when they fall short.

• Real-Life Example:
  A car break-in left her scared and needing comfort; her boyfriend didn’t rise to the moment, though he later apologized. Nick validates her communication but encourages patience and not pathologizing partners over normal human flaws:

  "Having our partners magically just do the right thing every time...is great, but kind of unrealistic. ...It’s the most we can hope for.” ([100:52])

• Fear of Having Children / Commitment:
  Margaret is unsure if she wants a family, scared of repeating her mother’s pain or enduring betrayal.

  “If having kids is something you think about, don’t make that decision out of fear.” ([116:28])

Notable Quotes

• Nick: "Our parents can be examples of who we want to be or who we don’t want to be. And in almost everyone’s case, they play a bit of both." ([93:00])
• Margaret: “I think I’m just trying to be the opposite of [my dad]. And it’s really hard when I’m surrounded by it all the time.” ([92:45])
• Nick: “Try not to add unnecessary pressure on yourself or the relationship or him if it doesn’t need to...sometimes you have to ask: Is this important for me to address, or do I just want to be right?” ([113:05])

Episode Highlights & Memorable Moments

• Nick’s Relationship Realism:
  Nick’s approach is consistently practical, bordering on blunt: “You can always break up. There’s no guarantees.”
• Cultural Shift on Male Assertiveness:
  Nick (re: Sydney’s guy): “Men under 35 don’t know how to be assertive without being pricks—or else are so beta, they’re scared to man up. Women want a guy who says, 'No, I don’t want you being with anyone else.'” ([38:41])
• Parent as Example or Warning:
  “Our parents are always examples—of who we want to be or don’t want to be… They can be both.” ([93:00])

Timestamps

• [01:01] – Blair: The 15-year “buddy” saga
• [09:30] – Nick on what it takes to change a longterm dynamic
• [14:50] – On letting go of nostalgia as the only glue
• [18:30] – The importance of confident confrontation
• [22:40] – Blair's self-respect and motivation to move on
• [31:53] – Sydney on commitment aversion and the mullet ick
• [39:51] – Building rapport/fear of labels (Nick)
• [49:12] – Rite of passage: heartbreak and learning
• [54:45] – How to define the relationship correctly
• [57:42] – Balancing career, friends, and relationship
• [61:57] – “Grow up a little bit”—Nick to Sydney
• [73:20] – Margaret: Parental cheating, secrets, trust issues
• [80:59] – Nick on empathy for closeted parents
• [90:16] – How closure sometimes can only come from yourself
• [100:52] – Accepting imperfections in relationships
• [106:32] – On being right vs. being happy
• [116:28] – Parenting decisions from fear vs. hope

Final Thoughts

Nick Viall’s advice hinges on radical self-honesty and assertive communication—whether you’re pitching a relationship upgrade after years of ambiguity, facing your own ambivalence about commitment, or learning to let go of family-of-origin trauma. His blend of empathy and directness draws a firm line between understandable anxieties and self-sabotage, urging listeners not to let perfection, fear, or a need to be right keep them from happiness, growth, or love.

For further updates or to follow up with Nick, listeners are always encouraged to send their outcomes and feedback to the show!