The Viall Files

Episode 996: Ask Nick – Two Hot Best Friends Are Fighting Over Me

Date: September 8, 2025
Host: Nick Viall

Episode Overview

This “Ask Nick” episode dives headfirst into the tough realities and nuances of modern dating. Nick Viall, alongside a revolving cast of Household regulars, takes calls from listeners grappling with everything from cultural disparities in dating to navigating attraction between friends—and even whether it’s okay to ask out your doctor. Expect frank, sometimes humorous, always insightful commentary on gender dynamics, dating apps, boundaries, and the evolving rules of relationships in 2025.

Key Discussion Points & Time-Stamped Highlights

1. Is the Grass Greener Abroad? Living the European Dating Fantasy

Caller: Taylor, 36
[03:30–33:52]

Summary

Taylor calls in frustrated with the American dating scene, wondering if she literally needs to leave the country to find a boyfriend. After a vibrant trip to Europe, where men seemed more confident, open, and willing to approach women, Taylor questions if she’s simply in the wrong country—or if rose-colored glasses are at play.

Main Insights

• US vs. European Dating Culture:

  • Stateside, men reluctant to approach; culture of caution dominates
  • In Europe, men are proactive but not aggressive, making for relaxed, enjoyable interactions
  • Taylor: “...we’d be out to dinner and the men at the next table would say, like, when you’re done, come over and join us...” (04:30)

• The Shrinking “Dating Pool” & App Fatigue:

  • Taylor bemoans lack of attractive, eligible men in large US cities: “...it just feels like there’s not even a pool of great guys to choose from.” (07:59)
  • Dating apps like Raya and Hinge are “actively depressing,” with algorithms warping standards and narrowing perceived options

• Culture of Caution in the US:

  • Nick explains how online discourse and stories about “creepy men” (e.g. from viral social videos) have left many men fearful of approaching women altogether:

    "There’s a lot of women online telling men and young men, do not approach me. Do not talk to me… There’s enough bad actors out there who have done some terrible things, that now all men are getting the message." (10:07)

  • Women have been socialized to expect men to approach, but today’s climate undermines this

• Shifting Strategies:

  • Nick recommends banding together with friends for NFL Sunday “sports bar” outings—a setting where casual interaction is more socially smooth, suggesting,

    “A group of young, attractive women at a table will stand out at a sports bar. You’re going to get approached and… have a good time.” (17:36)

• Broader Diagnosis of Dating Culture:

  • Nick theorizes that dating app and social media culture has “warped the perspective of women more than men,” driving up expectations and reinforcing unattainable standards
  • Both men and women are struggling:

    “There needs to be kind of a dating revolution that’s not in digital.” (21:49)

  • On needing to challenge assumptions and try new approaches:

    “You’re going to have to be willing get to know men that your initial instincts wouldn’t be to swipe right on.” (23:02)

Notable Moments

• Taylor admits to “hooking up” on her European trip:

  “The next night with a different person that I met.” (09:34)

• Nick waxes philosophical about the privileges of being a hot, tall guy in 2025:

  “The greatest privilege in modern history is men who are over 6 foot.” (18:31)

• Advice to “try out” real life mixers or create in-person singles events; Nick notes their upcoming work with Netflix highlighted how eager people are for curated, offline connections (27:19)

2. Is It Okay To Ask Out Your Doctor?

Caller: Allison, 33
[37:45–49:36]

Summary

Allison’s general practitioner moves away, replaced by a charismatic, charming doctor “about her age." Smitten and single, she wonders: Is it taboo to follow her now-former doctor on Instagram or even make a move?

Main Insights

• The Doctor “Smoke Show”:

  • Allison describes her new GP as “a complete smoke show... charisma in the office, as the kids say.” (38:50)
  • She’s done “all the girl squad stalking” and found mutual interests, but little about his relationship status

• Protocols & Strategies:

  • Nick encourages her:

    “Of course you should shoot your shot. For sure, right? I don’t know, especially nowadays it seems like there are more doctors than eligible men.” (39:44)

  • Weighs potential scenarios from Instagram requests, jokes about HIPAA barriers, and ultimately lands on:

    “You could DM him like, ‘I have two questions. One, do you know any other good doctors because I’m looking for a new one, and two, do you want to go out to dinner?’” (46:09)

• Navigating Embarrassment & Practicalities:

  • Allison is worried about seeming forward, but Nick encourages boldness:

    “What do you have to lose? A new doctor? A little pride?” (47:02)

  • If refused, the only fallout is inconveniently finding a new GP

3. Should I Date This Guy When I’m More Into His Best Friend?

Caller: Taylor, 27
[52:40–91:21]

Summary

After meeting two attractive friends at a wedding (let's call them Jack and Austin), Taylor found herself more drawn to the unavailable one (Jack), but now the friend (Austin) is actively pursuing her. She wonders whether she should ignore the “what if” with Jack and give Austin a shot, or hold out hope that timing will work out with the one she “really wants.”

Main Insights

• The Love Triangle:

  • At the wedding, Jack flirts and says, “If you ever find yourself not in a relationship, come find me.” (53:11)
  • Fast forward: Taylor is single, but Jack is now in a serious relationship; Austin (his friend) asks her out

• Navigating Friend Dynamics:

  • Taylor’s worry: If she dates Austin, she’ll “ruin any chance” with Jack, should he become single again.
  • Nick pushes her to be realistic:

    “Let’s forget about guy number one, Jack, for a second.” (60:29)

  • Advises, “You don’t know Jack.” Points out she may be “building him up in her head” based on a single, memorable encounter (65:00)

• Dating With Intentionality & Boundaries:

  • Taylor is clear about her values—no casual sex, wants marriage/family, observes her own pattern of falling hard and fast
  • Nick commends her self-awareness and encourages her to take things slow, to avoid being swept up by the “challenge” aspect that drives some men:

    “The more confident you are about what you want and showing more than telling... you’ll find out pretty quickly where Austin stands.” (75:08)

• How to Handle Physical Intimacy:

  • Taylor says, “If my clothes came off at all, I’d be like, let’s have sex. I don’t think, personally, I could... do anything more than kiss without just giving in fully.” (80:12)
  • Nick suggests easing into physicality slowly (e.g., making out, second base) to gauge Austin’s post-challenge interest

• Letting Go of The Fantasy:

  • Nick zeros in: “You gotta let Jack go.” (66:40)
    • “If he knows you’re single and is interested, he’ll make a move.”
    • Admits that in this scenario, “there’s no perfect path forward”; encourages her to focus on what’s real and present

• Real-World Advice:

  • On sexual boundaries: “Just be careful... if you want to kiss a guy, kiss the guy. Don’t hold out to be difficult or... dangling a carrot and being like, I’m not. If you’re feeling it, just make out right. But that’s when you have to know yourself.” (84:02)

Notable Quotes

• On navigating the competition between “hot guys”:

  “The difference between what you experienced with him [Jack] and what he experienced with you is... you had a moment. For him, he was pulling that. He was pulling that [flirtation]...” (67:58)

• On boundaries and self-respect:

  “Boundaries are for you. That’s great. And you’ve definitely saved yourself probably a lot of emotional distress and frustration by being able to hold that line.” (59:15)

• On tackling disappointment:

  “At some point, you can’t protect yourself from frustration, pain, disappointment. All you can do is what you’re doing now, which is be more intentional.” (78:38)

Overarching Themes & Takeaways

• Dating Culture Is Broken, But You’re Not Alone:
  Both men and women feel lost in today’s landscape—dating apps, social media, cultural anxieties, and shifting norms have shaken everyone’s confidence and narrowed perspective.

• Intentionality & Self-Awareness Matter More Than Ever:
  Holding boundaries, articulating what you’re looking for, and resisting the pull of “fantasy” crushes is the best protection against heartbreak and confusion.

• Offline Is Underrated:
  Real-life encounters—from sports bars to mixers—are staging a comeback, and intentional efforts to “put yourself out there” can reset your dating experience.

• Shoot Your Shot. Sometimes Literally:
  Whether it’s a doctor or a crush’s friend, sometimes you just have to move boldly (and decide you can handle the awkwardness if it goes south!).

Memorable Quotes & Timestamps

• "The greatest privilege in modern history is men who are over 6 foot. Because the way women treat them…” — Nick (18:31)
• “Try to replicate the things that are working for you when you’re traveling.” — Nick, on bringing “vacation energy” home (31:00)
• “Of course you should shoot your shot. For sure, right? I don’t know, especially nowadays it seems like there are more doctors than eligible men.” — Nick (39:44)
• “You gotta let Jack go.” — Nick (66:40)
• “If you want to kiss a guy, kiss the guy. Don’t hold out to be difficult… If you’re feeling it, just make out.” — Nick (84:02)
• “At some point, you can’t protect yourself from frustration, pain, disappointment. All you can do is what you’re doing now, which is be more intentional.” — Nick (78:38)

Final Thoughts

Nick and his callers illustrate the daunting mix of hope, cynicism, humor, and vulnerability that defines modern dating. They show the importance of honesty—with others and yourself—embracing risk when it’s warranted, and occasionally mixing things up (be it at a European wine bar or a Sunday sports bar). If you’re stuck, you’re in good company, and sometimes the best thing you can do is put yourself out there—even if it feels a little chaotic.