We Might Get In Trouble For This

We might get in trouble for this Team
  • 5.0 (3)
  • Arts

Kerri, a Gen X comedian and author, and Suze, an elder Millennial mama who’s totally outnumbered, are two old friends diving into life from opposite sides of the spectrum. From pop culture and love to divorce, faith, and everything in between, they’re a little unhinged, a little risky, and guaranteed to get in trouble along the way. 

Episodes

  1. Aug 20

    Ep 14, Chrisitian dating boundaries after 40.

    Dating over 50 is apparently just being 16 again—except now you have dating apps, divorce, teenagers, hormones, faith, and a much clearer idea of what you actually want. On this episode of We Might Get in Trouble for This, Kerri Pomarolli and Suze catch up on the latest dating developments, including the ongoing saga of Kerri’s sarcastic “pirate,” a surprise real-life date with a very cute local guy, and the bigger question underneath all the dating shenanigans: Where is the long-game guy? Kerri and Suze get honest about dating after divorce, Christian dating, being equally yoked, chemistry versus compatibility, emotional intimacy, and physical boundaries in a Christian relationship. They also talk about sex, marriage, faith, and why finding someone who shares your beliefs can mean more than simply finding someone who checks the “Christian” box. There are laughs, questionable dating decisions, a very memorable story and a surprisingly heartfelt conversation about wanting a partner who will actually be there when life gets hard. Because sometimes you want the funny guy. Sometimes you want the hot guy. But eventually, you start wondering: Where’s my guy? Follow We Might Get in Trouble for This: Instagram: @wemightgetintroubleforthispod Facebook: @wemightgetintroubleforthispodcast Watch full episodes at: https://www.youtube.com/@WeMightGetinTroubleforThisPod⁠�

  2. Aug 11

    Episode 13, genX dating, Kerri went to a speed dating event and immediately lost her mind.

    Kerri took a very big left swing in the Gen X dating world — and ended up kissing a 42-year-old, questioning every decision she’d made that week, and making an 11:45 PM phone call she probably should have slept on. Meanwhile, the “Pirate” is still texting, the dating apps are getting deleted, and Kerri is realizing maybe God has been trying to get her attention. On We Might Get in Trouble for This, Kerri Pomarolli and Suze unpack dating after divorce, Gen X dating, Christian dating, attraction, boundaries, hormones, dating apps, and what happens when chemistry and your convictions don't exactly agree. There are speed-dating stories, a very confident younger man, a margarita-fueled confrontation, and a surprisingly heartfelt conversation about faith, friendship, dating after 50, and learning how to say no without feeling responsible for someone else's feelings. What happens when you finally feel that spark again after years of being single? And how do you know when you're following your heart… versus just chasing a shiny object? Follow We Might Get in Trouble for This: Instagram: @wemightgetintroubleforthispod Facebook: @wemightgetintroubleforthispodcast

  3. Aug 8

    Ep 12, Love bombing, dating apps and federal agents FBI

    One text message completely changed Kerri's dating life... and confirmed the gut feeling she couldn't shake. What started as another Gen X Dating Diaries update quickly turned into one of the wildest dating stories she's ever shared. In Episode 12 of We Might Get in Trouble for This, Kerri Pomarolli and Suze unpack what happened after Kerri reached out to a mutual acquaintance—only to discover the "nice Christian guy" she'd been talking to was living a very different story than the one he was presenting. The conversation turns into a funny, honest discussion about love bombing, dating after divorce, trusting your instincts, Christian dating, dating apps, boundaries, and why being "nice" isn't the same thing as having character. Of course, there are plenty of laughs along the way, including updates on the Pirate, an upcoming speed dating adventure, Gen X dating realities, and why middle-aged dating can make even confident adults feel like awkward teenagers again. Have you ever ignored your instincts because someone looked perfect on paper? What's the biggest dating red flag you've learned to recognize? Watch the full episode and join the conversation. Follow We Might Get in Trouble for This: Instagram: @wemightgetintroubleforthispod Facebook: @wemightgetintroubleforthispodcast Watch full episodes at: https://www.youtube.com/@WeMightGetinTroubleforThisPod⁠�

  4. Aug 4

    Episode 11, is Kerri the new GenX Bachelorette?

    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. Follow We Might Get in Trouble for This: Instagram: @wemightgetintroubleforthispod Facebook: @wemightgetintroubleforthispodcast Watch full episodes at: https://www.youtube.com/@WeMightGetinTroubleforThisPod⁠�

  5. Jul 29

    Gen X Dating Part 1 | Kerri Blocked the Italians and Went With Americans

    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

  6. Jul 28

    Gen X dating part 2, smitten or catfished?

    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

  7. Jul 13

    Kerri Should Not be Left Unsupervised.

    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

  8. May 13

    Is Kerri a Buzz Kill?

    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.

  9. Apr 22

    Did Kerri’s Mom Go to Vietnam to Meet Boys?

    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

  10. Apr 14

    What’s So Funny about Faith?

    🎙️ 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 logicTrauma + bad theology can deeply distort faithYou can feel heartbreak, anger, and compassion at onceJesus and people are not the same—don’t confuse themGod’s timeline is longer than our judgmentThe most Christ-like response is prayer, not condemnationAnd 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

  • 10 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

Kerri, a Gen X comedian and author, and Suze, an elder Millennial mama who’s totally outnumbered, are two old friends diving into life from opposite sides of the spectrum. From pop culture and love to divorce, faith, and everything in between, they’re a little unhinged, a little risky, and guaranteed to get in trouble along the way. 

Information

  • Creator
    We might get in trouble for this Team
  • Years Active
    2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © 2026 We Might Get In Trouble For This
  • Show Website
    We Might Get In Trouble For This