The Viall Files – E1038 Ask Nick: "My BFF Is Pregnant With My Ex"

Date: November 24, 2025
Host: Nick Viall
Guests/Household: Natalie Joy, Leah, household members
Episode Theme:
A holiday-tinged "Ask Nick" edition, giving straight-talking, empathetic advice to listeners on complicated love, friendship, and life situations. This episode features confessions and questions about marriage readiness, friendship boundaries, and whether bad kissing is a relationship dealbreaker—all sprinkled with Nick’s signature wit, honest takes, and the group’s candid discussion.

Episode Overview

This “Ask Nick” is set against a cozy, holiday backdrop, full of personal anecdotes, playful games, and honest listener dilemmas. The episode has three major calls:

1. A woman wondering how to convince her boyfriend of seven years to propose.
2. A fraught friendship dilemma—a woman’s best friend is pregnant by the same man she once hooked up with.
3. Whether a great-on-paper guy who is a “terrible kisser” can (and should) be salvaged.

1. Holiday Warm-Up: The Household Gets Festive

Timestamps: [02:57]–[09:09]

Holiday Game: "This or That" (Sponsored by Starbucks)

• The group plays a rapid-fire holiday “this or that” game to get into the seasonal spirit.
• Topics debated with playful banter: turkey vs. sides, stuffing vs. green bean casserole, hot vs. iced drinks, gingerbread vs. sugar cookies, real or fake tree, and more.
• Natalie shouts out caramel brulée lattes, Nick stays loyal to peppermint mocha.
• Memorable Moment:
  • Natalie on starting Christmas early:
    [07:46] Natalie: “Definitely launch day... No, as early as possible!”
• Reflection: Family traditions, nostalgia, and small joys set the stage for the heavier calls to come.

2. Caller #1: "How Do I Convince My Boyfriend to Propose?"

Timestamps: [09:22]–[37:41]
Caller: Kate, 25

Situation Recap

• Kate has been with her boyfriend for 7 years—they started dating at 18.
• She owns a home, is the breadwinner, they live together most of the week.
• She's ready for marriage; he's not. Vague reasons from him: “It’s scary, it’s a big commitment.”
• Kate feels insecure and anxious, “Why isn’t he ready?” She wonders if she’s enabling his lack of motivation.

Key Advice & Insights

Men and Marriage Readiness

• Nick:
  “There’s gotta be a thing… that’s stopping him from being like, this is the woman I want to marry. He lacks that certainty." [12:36]
• Nick highlights generational change: People settle down later, often waiting to “figure out their purpose” before big commitments.

Money, Purpose, Masculinity

• Kate’s BF is unstable career-wise (freelance videography, bartending), while she is secure.
• Nick's Analysis:
  • Men often want to have “their thing” figured out before marrying.
  • Sometimes it’s less about money and more about purpose and masculinity.
  • Unspoken traditional values (“men should provide”) may fuel his hesitation.

Action Steps for Kate

• Encourage him to share his dreams and uncertainties; create a supportive space for his vulnerability.
• Stop guessing his needs—have deeper, goal-oriented conversations.
• Quote:
  “You have to… be willing to maybe hear an answer that might hurt your feelings... It might feel almost like a personal attack, even if he doesn’t mean that... but you really have to talk with him and get him comfortable enough to open up.” [21:04] Nick

On Financial Enabling

• Kate frequently pays his car payments, provides materially.
• Nick’s Firm Advice:
  • “You’re giving him just enough to not want to figure his own shit out... You shouldn’t be paying his car payments.” [33:39]
  • Draws the “feed a man a fish, teach him to fish” analogy—she’s making his stagnation a comfort zone.

Should She Wait?

• If he gives her vague timelines (“two or three years”), Nick says he’s likely just “kicking the can.”
• Quote:
  • “He’s just hoping he’ll feel differently in three years, but he’s not doing anything about it that will make him feel different.” [36:02]

Nick's Bottom Line:

• Recalibrate expectations.
• Stop full financial support unless there’s an equal commitment (i.e., marriage).
• Focus on mutual dreams/goals as individuals and as a couple.
• Don’t “convince” him to propose—help him find purpose, then see if your paths align.

3. Caller #2: "My Best Friend Is Pregnant With My Almost Baby Daddy"

Timestamps: [40:37]–[51:36]
Caller: Melanie, 24

Situation Recap

• Years ago, Melanie had a “situationship” with a guy—her long-time hookup partner, whom she considered an "almost baby daddy" until a paternity test said otherwise.
• Her best friend (since grade school) is now pregnant by this same guy. Melanie feels weird, hurt, and unsure if the friendship is over or if her feelings are justified.

Key Discussion Points

Sorting Out the Feelings

• Nick:
  “You caring about her getting pregnant with this guy is giving a little... like, you care about a guy you shouldn’t be caring about.” [42:28]
• Melanie is now in a relationship with another man, has two kids, and insists she wants to be happy for her friend, but the situation feels weird and loaded.

Assessing "Friendship Code Violation"

• The “almost baby daddy” was never a serious partner, just a long-standing college hookup.
• Nick emphasizes you don’t get to “call dibs” on casual hookups.
• Unless her best friend acted to spite her, it’s not a friendship-ending betrayal.
• If Melanie is still projecting “weirdness” or resentment, her friend will sense it, risking a drift.

Tools for Moving Forward

• Nick suggests Melanie reach out and affirm the friendship:
  [50:14] Nick: “I want you to know I’m just really happy for you... I value this friendship... and I’m always here for you and I don’t want you to ever feel like you can’t talk to me.”
• “Focus on what you have... This [energy] is a waste.” [51:02] Nick

Key Takeaways

• Emotional closure with flings/situationships is necessary—don’t project leftover feelings into friendship.
• If her gut says her friend was malicious, that’s a separate issue; otherwise, lead with warmth.
• Make space for honesty and mom-to-mom connection as their kids grow up together.

4. Caller #3: "Is Being a Bad Kisser a Dealbreaker?"

Timestamps: [55:32]–[73:18]
Caller: Lindsay, 29

Situation Recap

• Lindsay’s first date with a guy who is "perfect on paper" (great job, clean apartment, similar values) ends miserably when he turns out to be a “disastrous” kisser.
• The kiss is described as: “Niagara Falls, if you were standing at the bottom with your mouth wide open... no coordination, like he was possessed by some... I’m serious. It was so strange.” [56:21] Lindsay
• She wonders if it’s salvageable or a dealbreaker.

The Bad-Kisser Dilemma

Can Bad Kissing Be Fixed?

• Nick:
  • Asks if she’s ever “coached” someone before.
    “You don’t want to jump to conclusions, but a 33-year-old man who’s this bad potentially isn’t coachable.” [60:21]
  • Suggests some men become “cocky” if they’re attractive and single too long; “Maybe he just needs to be checked.”
  • Sometimes porn or a lack of feedback leads to weird habits.
• Lindsay worries she can't “un-ick” herself; the kiss killed her attraction.

Giving Feedback for Growth

• Nick: Feedback is possible if the guy is open and coachable.
• “Kissing is like dancing… I want you to kiss with me… I feel like we’re not in sync when we kiss.” [64:22] Nick (suggested script)

Red Flags

• Lindsay describes a moment where he was “turned on” by excess saliva, declaring “that’s hot,” which she labels “freaking weird.” [67:12]
• Nick says every kink is valid, but introducing them too early, without consent, is “a bit aggressive” and self-centered.
• What matters: Is he “interested in what you like” and willing to listen, rather than just seeking his own turn-on?
• Nick: “The difference between whether he’s one of the good ones and not is his willingness... if you come in with kindness… if you make it about this is what I like and are you interested in turning me on?” [72:23]

Next Steps

• Nick recommends building rapport, trying a second date, gently addressing the kiss, and gauging how open he is to feedback.
• Lindsay is empowered to decide—if he’s defensive or can’t adapt, “that’s your answer.”

Notable Quotes & Moments

• Nick on marriage expectations:
  “You’re not sitting around for a feeling, like he is. You’re paying his rent, supporting him… you’re doing just enough where he’s kind of comfortable with his lifestyle, but deep down, he’s not fulfilled.” [36:02]
• On friendship and closure:
  “Focus that energy on being present with your partner instead of, in a weird way, giving more energy to some hookup guy about what he means to you or doesn’t mean to you or whether you should have ‘dibs’.” [51:02]
• On giving feedback about bad kissing:
  “I want you to kiss with me… I feel like we’re not in sync.” [64:22]

Timestamps for Key Segments

• Holiday Segments & Household Banter: [02:57]–[09:09]
• Caller #1 (Marriage Readiness): [09:22]–[37:41]
• Caller #2 (BFF Pregnant by Ex): [40:37]–[51:36]
• Caller #3 (Bad Kisser): [55:32]–[73:18]

Episode Tone

• Warm, candid, sometimes blunt but always well-intentioned.
• Insightful takes and humor, even on tough topics.
• Nick leads with empathy, balances realism and optimism.

For the Uninitiated Listener

This episode dives deep into real relationship messiness—commitment fears, friendship awkwardness, sexual chemistry. Nick’s advice is practical, often tough-love, but deeply human. Listeners can expect honest, actionable steps and permission to set boundaries, have tricky conversations, and focus on their own growth.

Key Takeaways:

• Don't put your life on hold waiting for feelings—seek clarity and shared goals.
• You can’t claim ownership over exes or hookups; friendships require directness and generosity.
• Chemistry matters—and so does mutual respect and communication (yes, even about kissing).
• If it’s hard to talk about, it’s probably a conversation worth having.

End of Summary