Kerri Pomarolli's dating life officially became a sitcom. One nine-hour first date, one incredibly thoughtful Christian dad, one accidental Instagram crush... and absolutely no clue what's happening next.
In this episode of We Might Get in Trouble for This, Kerri and Suze unpack the latest chapter in Kerri's Gen X dating adventures. There's the mysterious "Pirate" who planned an unforgettable first date but never asked for a second one. Then there's the thoughtful Christian guy who checks almost every box—but keeps texting without putting an actual date on the calendar. And somehow, an Instagram dating influencer unexpectedly enters the story too.
Along the way they talk about dating after 50, Christian dating, modern dating apps, mixed signals, intentional relationships, parenting while dating, attraction, boundaries, prayer, and why today's dating culture can feel like negotiating with the FBI.
It's funny, honest, awkward, relatable—and exactly what happens when two Gen X friends process dating in real time.
Have you ever liked someone who just... wouldn't make a move? Are people overthinking dating today?
Watch and tell us who you're rooting for: The Pirate, the Nice Christian Guy... or someone else entirely.
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After 12 years away from dating, Kerri finally has a date—and she is handling it with all the maturity of an eighth grader.

In Episode 9 of We Might Get in Trouble for This, Kerri says goodbye to the flirty Italian men, joins an American dating app and unexpectedly connects with a fellow Gen Xer over Christopher Cross, yacht rock, sarcastic humor and marathon phone calls.

What begins with “I don’t think we’re a match” somehow turns into hours of conversation, exchanged photos, one near-breakup caused by Kerri’s level-13 sarcasm and an actual first date.

Kerri and Susie talk honestly about dating after divorce, dating over 50, Christian dating, attraction, boundaries, online dating and how much of your real life you should reveal before meeting someone in person.

Can a deeply Christian woman date someone who may not share her faith? Will their phone chemistry translate in person? And how long can Kerri keep pretending she hosts karaoke?

Watch for an honest and hilarious conversation about reentering the dating world, finding chemistry after divorce and trying to keep romance analog in a very digital age.

#kerripom #GenXDating #DatingAfterDivorce #DatingOver50 #ChristianDating #OnlineDating #HingeDating #FirstDate #ModernDating #WomenOver50 #SingleWomen #DatingPodcast #RelationshipPodcast #YachtRock #ChristopherCross #ComedyPodcast #WeMightGetInTroubleForThis
Learn about Kerri: kerripom.com

SEE KERRI LIVE! : kerripom.com/calendar

What more of Kerri's comedy?
Facebook: / kerripomarolli
Instagram: / kerripom
Tiktok: / kerripomarolli

00:00 — GLP-1 Jokes and the Opening Chaos
01:30 — Why Kerri and Suze Only Talk on the Podcast
02:24 — Kerri Blocks the Italian Men
04:11 — Back on an American Dating App
06:16 — “I Don’t Think We’re a Match”
09:02 — Music, Yacht Rock and the Gen X Connection
10:14 — The First Three-Hour Phone Call
14:02 — Kerri Cuts the Millennial Loose
14:51 — Sarcasm Nearly Ends the Gen X Connection
19:50 — Gina Takes Over the Phone Call
22:58 — Kerri Officially Has a Date
26:56 — Faith, Dating and Being Equally Yoked
32:35 — Will There Be Chemistry in Person?
39:51 — Dating Again After 12 Years
40:06 — Closing and Where to Follow the Podcast

Are We Dating or Just Texting?

Dating after divorce is already complicated—but add Christian dating, texting rules, attraction, catfishing fears, masculine energy, and the pressure to become a “Proverbs 31 woman,” and things get hilarious fast.

In this episode of We Might Get in Trouble for This, Kerri and Susie talk honestly about modern dating, Gen X relationships, online chemistry, faith, femininity, masculinity, virtual intimacy, and what women really want in a life partner.

Plus: Kerri has spent approximately 35 hours on the phone with a man she has never met—and the first date is officially happening.

Will the chemistry be real, or is she about to be catfished?

Watch now for an unfiltered, funny conversation about dating after divorce, Christian relationships, modern romance, and finding connection without playing games.

#kerripom​ #DatingAfterDivorce​ #ChristianDating​ #GenXDating​ #ModernDating​ #DatingPodcast​ #RelationshipPodcast​ #WomenOver40​

#SingleWomen​ #OnlineDating​ #MasculineEnergy​ #ChristianWomen​ #ComedyPodcast​ #WeMightGetInTroubleForThis​

Learn about Kerri: kerripom.com

SEE KERRI LIVE! : kerripom.com/calendar

What more of Kerri's comedy?
Facebook: https://www.facebook.c...
Instagram: https://www.instagram....
Tiktok: https://www.tiktok.com...

00:00 Intro and Suze’s medical update
02:55 Blocking the Italian men
05:25 Kerri joins a dating app
06:05 The Christopher Cross dating test
07:10 Meeting the Christian millennial
08:45 Enter the mysterious Gen Xer
12:20 Music creates an instant connection
18:15 Why grown men end text conversations
19:40 Choosing Gen X over the millennial
21:40 A prayer meeting changes everything
26:00 He discovers Kerri’s YouTube channel
27:55 Gina grabs the phone
32:15 Kerri officially has a date
34:00 When sarcasm nearly ends the relationship
38:10 When should faith enter the conversation?
42:00 Dating boundaries at 52
45:15 Will there be chemistry in person?
49:50 How much personal history should you share?
53:10 Can a calm relationship still be exciting?
55:25 Final thoughts and podcast outro

Kerri went to Italy with her daughter and accidentally came home with an international dating roster.

In this late-night episode of We Might Get in Trouble for This, Kerri reveals what happened when one viral video from Italy led to an inbox full of Italian men, flirtatious voice messages, dating-app dopamine and one very questionable return to Hinge.

After 12 years away from dating, she is suddenly navigating Christian dating, attraction, temptation, hormones, texting etiquette and the uncomfortable realization that she still enjoys being pursued.

Kerri and Susie also get honest about faith, guilt, grace, boundaries, discernment and the difference between healthy desire and a very distracting man emerging from the Italian ocean.

Is this a dating awakening, a hormonal emergency or simply a cry for adult supervision?

Watch for an honest and hilarious conversation about dating after divorce, dating over 50, Christian relationships, modern romance and trying to hear God while your phone keeps lighting up.

#GenXDating #DatingAfterDivorce #DatingOver50 #ChristianDating #HingeDating #ModernDating #ItalianMen #Hormones #MenopauseHumor #ChristianWomen #SingleWomenOver50 #DatingPodcast #ComedyPodcast #FaithAndDating #WeMightGetInTroubleForThis #kerripom

Learn about Kerri: kerripom.com

SEE KERRI LIVE! : kerripom.com/calendar

What more of Kerri's comedy?
Facebook: https://www.facebook.com/KerriPomarolli/
Instagram: https://www.instagram.com/kerripom/
Tiktok: https://www.tiktok.com/@kerripomarolli

This episode starts light—antibiotics, diet culture, and a very questionable Fen-Phen story—but quickly turns into something much deeper.

Kerri is joined by her mom, Barbara Pomarolli, who shares her extraordinary experience serving as a Red Cross worker on a Navy hospital ship during the Vietnam War. At just 24, she was one of only two women selected for the role.

From caring for wounded soldiers and writing their final letters home, to navigating life in an active war zone, Barbara’s story is equal parts heartbreaking, inspiring, and unforgettable—with a few unexpected moments of humor along the way.

http://kerripom.com/

https://tatcha.com/

⏱️ Timestamps

00:00 – Intro + near-death stories & antibiotics nostalgia
01:30 – Diet culture throwbacks (SlimFast, Dexatrim)
02:30 – KERRI’s Fen-Phen story + LA pressure
03:30 – Cancer scare update & “celebrating being alive”

04:20 – Introducing Barbara Pomeroli
05:00 – Chosen for Vietnam (Red Cross)
07:00 – Decision to go + family reactions

09:30 – Arrival in Vietnam + first impressions
12:30 – Life on the USS Repose

15:00 – Role on the ship + helping patients
17:00 – Writing letters for wounded soldiers
19:00 – Death, loss & final letters

20:30 – Burn unit realities + emotional toll
22:00 – Comforting soldiers + human connection

24:00 – Daily life + entertainment shows
26:30 – Faith & church on the ship

29:00 – Returning home during anti-war protests
31:00 – Long-term health effects

33:00 – Legacy, veterans & reflection

34:30 – “We Don’t Hate It” (skincare segment)
36:00 – Wrap-up & where to follow

KERRI and Suze talk about friendship rejection, social media triggers, emotional closure, and how childhood experiences shape adult relationships. From feeling left out of parties to learning how to move forward with maturity, they unpack rejection with humor, honesty, and faith.

Plus: Suze apologizes, resistance leggings, and colonoscopy prep somehow enter the chat.

Timestamps

00:00 – Fan mail + life updates
02:00 – Feeling excluded from a party
05:00 – Childhood rejection memories
08:00 – Family dynamics & emotional wiring
11:00 – Perfection, friendships & expectations
14:00 – Seeking closure
17:00 – “It’s not always about you”
19:00 – Choosing your inner circle
21:00 – Controlling your response to rejection
24:00 – Suze Apologizes
26:00 – Resistance leggings review
28:00 – Colonoscopy humor & outro

📧 wemightgetintroubleforthis@gmail.com
Available on Spotify, Apple Podcasts, Amazon Music & more.

🎙️ Episode Show Notes

Title: What’s so Funny About Faith?

In this deeply honest and vulnerable episode, Kerri and Suze jump from lighthearted life updates into a powerful conversation about faith, trauma, deconstruction, and the tension between personal pain and public expression.

From airport flirtations sparked by a bold “Jesus is better” hat to a sobering discussion about a fellow comedian’s journey away from Christianity, this episode explores how life experiences—especially trauma—can shape belief systems.

They wrestle with big questions:

• What happens when someone walks away from faith?
• Is it rebellion, pain, or something deeper?
• How should Christians respond—with anger, heartbreak, or compassion?

Suze shares a deeply personal story about how harmful church leadership impacted her trust in Christianity, while Kerri reflects on her own perspective shaped by a positive faith upbringing. Together, they model what it looks like to hold truth, emotion, and empathy at the same time.

The episode ultimately lands on hope: that faith journeys are rarely linear, God plays the long game, and no one is beyond redemption.

Key Takeaways;

• Pain often shapes belief more than logic
• Trauma + bad theology can deeply distort faith
• You can feel heartbreak, anger, and compassion at once
• Jesus and people are not the same—don’t confuse them
• God’s timeline is longer than our judgment
• The most Christ-like response is prayer, not condemnation
• And as always- be kind.

TIMESTAMP

00:00 Intro & life updates

00:58 Beauty mishaps & Nair story 😂

02:42 “Jesus is better” hat & airport moments

04:36 Comedian’s faith journey begins

06:24 Fame, distance & public deconstruction

09:00 The Prodigal Daughter reaction

10:28 Faith vs Hollywood pressure

12:00 Church trauma & personal story

16:30 Why people walk away from faith

20:02 How upbringing shapes belief

24:48 When faith becomes unsafe

26:19 Jesus vs people

30:16 Success, comparison & compromise

34:13 Comedy, pain & storytelling

35:37 God plays the long game

36:44 Meaning of “Prodigal Daughter”

37:05 Final thoughts on grace

38:06 “We Don’t Hate It” segment 😂

40:00 Outro