The Viall Files

E1038 Ask Nick - My BFF Is Pregnant With My Ex

November 24, 2025

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  • For the caller whose boyfriend is delaying marriage after seven years, the primary hurdle may be his professional uncertainty and feeling unsettled about his individual purpose, rather than the commitment itself. 
  • The host advises Caller 1 to stop financially enabling her boyfriend and instead focus on creating a supportive environment where he feels comfortable sharing his professional dreams before marriage can be prioritized. 
  • Caller 2, whose best friend is pregnant with her past hookup, is advised that she has no right to feel betrayed as she had no claim on the man, and she should focus her energy on her current partner and family rather than the awkward situation. 
  • For Caller 3, a man being 'perfect on paper' is insufficient if the physical chemistry, specifically kissing, is exceptionally bad, suggesting that a lack of basic physical compatibility after only one date is a significant red flag. 

Segments

Intro and Holiday Game
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(00:00:00)
  • Key Takeaway: The Viall Files kicked off the holiday season with a Starbucks-sponsored ‘This or That’ game featuring the household.
  • Summary: The episode opened with sponsor reads for Progressive Insurance and Amazon Music, followed by Nick Viall and his wife Natalie engaging in a holiday-themed ‘This or That’ game. Participants drank Starbucks holiday beverages like the Peppermint Mocha and Caramel Brulee Latte while answering questions about Thanksgiving traditions. The game served as a warm-up segment before addressing listener questions.
Seven-Year Relationship Marriage Delay
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(00:09:16)
  • Key Takeaway: A 25-year-old caller’s seven-year relationship delay in marriage is likely rooted in her boyfriend’s professional uncertainty and feeling unsettled about his individual goals.
  • Summary: Caller 1, Kate, has been with her boyfriend since age 18 and feels ready for marriage, but he cites fear and commitment issues without providing clear reasons. Nick suggests the boyfriend’s lack of career fulfillment, especially since Kate is the primary breadwinner, makes him hesitant to ‘settle down’ before figuring out his personal purpose. The advice centers on stopping financial support and having deep conversations about supporting each other’s individual dreams.
BFF Pregnant by Ex-Hookup
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(00:40:29)
  • Key Takeaway: A woman should not feel betrayed or make a friendship awkward over a pregnancy resulting from a past hookup partner who is not her current partner.
  • Summary: Caller 2, Melanie, is uncomfortable because her best friend is pregnant by a man she used to hook up with for years, even after Melanie started her current relationship. Nick emphasizes that Melanie has no ‘dibs’ on a casual hookup partner and that her current focus should be on her existing family unit with her partner. The key action is for Melanie to proactively reassure her friend that the friendship is valued, especially while the friend is vulnerable.
Bad Kisser Deal Breaker
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(00:55:11)
  • Key Takeaway: While a bad kisser can be addressed with direct feedback, a 33-year-old man who has been out of relationships for three years and kisses poorly suggests a deeper issue with experience or connection.
  • Summary: Caller 3, Lindsay, is hesitant about a seemingly perfect 33-year-old man because his kissing was described as aggressively uncoordinated, leading her to question if it’s a dealbreaker after only one date. Nick notes that the man’s lack of recent relationship experience might contribute to his poor kissing skills. The advice suggests that if Lindsay is genuinely interested, she could offer direct feedback, but the severity of the kiss after one date warrants caution.
Giving Kissing Feedback
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(00:58:13)
  • Key Takeaway: Direct feedback on kissing should be delivered respectfully and timed appropriately, potentially waiting until commitment is established.
  • Summary: Giving a partner a “kissing note” is acceptable if done respectfully, but delivering harsh criticism immediately might be detrimental if the relationship is serious. Nick suggests that extremely direct feedback about poor kissing might be better reserved for after marriage, depending on the desired outcome. If the goal is to end things quickly, directness is fine, but if interested, nuance is required.
Coachability and First Date Impressions
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(01:00:02)
  • Key Takeaway: A 33-year-old man who is a perceived “one percenter” but a terrible kisser may lack coachability, which is a major concern.
  • Summary: The caller notes the man is tall, handsome, and generally seems like a high-value prospect, making his poor kissing skills confusing. A lack of coachability in this area suggests he might shut down or get defensive when receiving feedback. The caller’s friends suggest poor kissing is teachable, but Nick questions if a 33-year-old who is this bad is open to learning.
Pornography and Single Life Impact
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(01:01:31)
  • Key Takeaway: Excessive pornography consumption or prolonged single status might contribute to men developing poor or overly aggressive kissing habits.
  • Summary: The caller and Nick speculate that the man’s kissing style might stem from watching “weird porn” or being single for too long, leading to a lack of awareness about reciprocal intimacy. Nick agrees that porn consumption is a current problem affecting how some single men approach physical intimacy. This behavior suggests the man might be focused only on his own arousal rather than connection.
Gentle Feedback Strategy
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(01:02:29)
  • Key Takeaway: If interested in continuing, the caller should pause physical escalation, build rapport, and then frame the kiss issue as a lack of synchronization or ‘dance’.
  • Summary: Nick advises the caller to keep talking to the man for about a week to learn more about his background before addressing the kiss directly. When addressing it, the feedback should focus on feeling out of sync or lacking rhythm, suggesting a desire for romance and passion rather than outright criticism. The goal is to see if he is willing to adjust his approach based on her preferences.
Kink vs. Connection in Intimacy
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(01:07:00)
  • Key Takeaway: A man explicitly stating that excessive saliva during a first kiss is “hot” indicates a potential kink that was introduced presumptuously, prioritizing his turn-on over mutual connection.
  • Summary: The caller revealed the man enjoyed the gross, excessive saliva and called it hot, which Nick views as a major red flag regarding his focus in the bedroom. This behavior suggests he is more concerned with what turns him on rather than what turns his partner on, which is crucial in early relationship stages. The ultimate test is whether he is willing to listen to her preferences and adjust his behavior.
Final Advice and Next Steps
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(01:12:40)
  • Key Takeaway: The man’s reaction to kind, non-patronizing feedback about her preferences will definitively reveal if he is a good partner or merely cocky.
  • Summary: The caller should spend the next week building rapport to make the subsequent conversation about intimacy feel safer. If he responds positively to her stating what she likes and shows genuine interest in turning her on, it is a green flag; if he dismisses it, it confirms a red flag regarding his self-centeredness.