We Might Get In Trouble For This

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Kerri may have finally met a man who checks enough boxes to make her stop overthinking — and, naturally, she has absolutely no idea what to do with that.

On this episode of We Might Get in Trouble for This, Kerri Pomarolli and Suze unpack the latest chapter of Kerri’s dating-after-divorce adventures: a long-distance date with a funny, confident Christian man who planned the date, made the reservations, showed up looking sharp, prayed before dinner, and apparently knows how to make a woman notice how he treats the people around him.

There’s chemistry. There’s faith. There’s generosity. There are songs sent by text. There’s a pirate update. And there’s Kerri trying very hard not to pick out the China patterns after date one.

Kerri and Suze talk about Christian dating, dating in your 40s and 50s, chemistry, attraction, intentional dating, being pursued without playing games, long-distance dating, faith and relationships, and the surprisingly difficult art of simply being present.

Can Kerri actually enjoy getting to know someone without deciding the entire future? And what does healthy pursuit look like when you’re old enough to know better but still feel like an eighth grader?

Watch or listen and ride the wave with us.

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Kerri Pomarolli’s dating life has officially become a podcast storyline—and this time, there may actually be a man on the other end of the phone.
On this episode of We Might Get in Trouble for This, Kerri and Suze catch up on Kerri’s latest dating adventure: a funny, confident Christian man she met through a dating app who initially seemed almost too good to be true. After plenty of texting, some Gen X suspicion, 90s R&B lyrics, Bible verses and a little “is this guy secretly in a Turkish prison?” speculation, he finally calls.
Now there’s another problem: he lives far away.   
Kerri and Suze talk about dating after divorce, Christian dating, long-distance relationships, dating with intention, vulnerability, compatibility, boundaries and the tendency to overthink every possible red flag before you've even had dinner together. They also revisit the Pirate and why losing a meaningful friendship can hurt deeply even when it was never a traditional romantic relationship.
And yes, there is a very serious discussion about whether Kerri should cancel a facial for a man.
Should she invite him to come see her? What does dating look like when you're both busy adults with kids and responsibilities? And can Kerri just meet the guy without turning dinner into a job interview?
Part two is definitely coming.
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Dating after divorce is already complicated. Now add a “pirate” who feels like a soulmate, a hot welder with a surprising Christian past, speed dating, dating apps, temptation, and Kerri wondering if God has basically put her in time-out.
In this episode of We Might Get in Trouble for This, Kerri Pomarolli and Suze unpack the very messy reality of Christian dating after divorce. Kerri shares updates on her dating life, including the man she calls “the pirate,” a recent date with a very attractive guy, and a speed-dating connection who is gorgeous, stable, creative—and formerly a pastor.
The conversation gets into dating after 40, Christian dating, dating apps, attraction, chemistry versus compatibility, faith and relationships, sexual boundaries, temptation, and the difference between someone being “great on paper” and actually being the person you want to build a life with.
And then there’s the question Kerri keeps coming back to: Is she listening to God—or finding increasingly creative ways to escape the dating time-out?
Could the right guy be the one who makes you laugh, understands you, and actually wants the same future? And what do you do when someone looks perfect on paper but something just feels… off?

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Dating after divorce is already complicated. Now add a “pirate” who feels like a soulmate, a hot welder with a surprising Christian past, speed dating, dating apps, temptation, and Kerri wondering if God has basically put her in time-out.
In this episode of We Might Get in Trouble for This, Kerri Pomarolli and Susie unpack the very messy reality of Christian dating after divorce. Kerri shares updates on her dating life, including the man she calls “the pirate,” a recent date with a very attractive guy, and a speed-dating connection who is gorgeous, stable, creative—and formerly a pastor.
The conversation gets into dating after 40, Christian dating, dating apps, attraction, chemistry versus compatibility, faith and relationships, sexual boundaries, temptation, and the difference between someone being “great on paper” and actually being the person you want to build a life with.
And then there’s the question Kerri keeps coming back to: Is she listening to God—or finding increasingly creative ways to escape the dating time-out?
Could the right guy be the one who makes you laugh, understands you, and actually wants the same future? And what do you do when someone looks perfect on paper but something just feels… off?

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Kerri Pomarolli and Suze are back with another brutally honest conversation about dating, faith, attraction, and the increasingly complicated world of being a Gen X woman looking for love after divorce.
Kerri has a lot to report: there’s the “pirate,” the man she talks to constantly and describes as a kind of soulmate even though they know they’re probably not long-game material. Then there’s the hot welder she met through speed dating—who turns out to have a surprisingly deep Christian background, including ministry experience and a Master of Divinity.
Naturally, things get complicated.
Kerri also tells Suze about a date where temptation got very real, the prayer warrior who sent her a Scripture at exactly the right moment, and her growing suspicion that God may have put her in a dating time-out.
The conversation explores Christian dating after divorce, dating apps, speed dating, attraction, sexual boundaries, faith differences, chemistry versus compatibility, trusting your gut, and the difference between finding someone attractive and finding someone you can actually build a life with.
Is Kerri supposed to stop looking? Is the Pirate actually boyfriend energy in disguise? And what do you do when someone is perfect on paper but your gut keeps saying, “Girl… no”?

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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?
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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?
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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.
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Watch full episodes at:
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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
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Watch full episodes at:
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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
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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