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Kerri Pomarolli is a grown woman with a career, kids, faith, and a whole lot of life experience. So why does one man have her feeling like she's 17 again, analyzing text messages and wondering if she's falling in love—or about to make a spectacular mistake?

On this episode of We Might Get in Trouble for This, Kerri and Suze get honest about dating after divorce, catching feelings too quickly, and the terrifying business of letting someone new into your life.

Kerri is navigating a new romantic connection, long-distance chemistry, Christian dating boundaries, and the urge to either go all in or run for the hills. She's also learning about anxious attachment, emotional vulnerability, and why a delayed text can suddenly feel like a full-blown relationship crisis. Meanwhile, Suze brings her own perspective on marriage, choosing a partner, and why the advice to marry someone who loves you more might deserve a second look.

There's Gen X dating humor, 90s romance comparisons, conversations about faith and attraction, and a more tender moment as Kerri reflects on her dad's hospice journey and what his love has taught her about the kind of partnership she wants.

Can you protect your heart without running away from something good? And when do you stop overthinking and let a relationship unfold?

Join Kerri and Suze for the funny, messy, honest conversation that dating in midlife deserves.

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Apparently, being over 50 does NOT mean Kerri has outgrown bad-boy energy. In Part 2 of this very late-night episode of We Might Get in Trouble for This, Kerri and Suze unpack a whirlwind dating situation involving chemistry, Christian dating, boundaries, jealousy, dating apps, and one very complicated crush.

Kerri catches Suze up on what has happened since the last episode — including her ongoing friendship with the Orange County guy, the mysterious “Cheffy,” and how two weeks of dating somehow turned into what feels like an entire year of romance.

There are puppy-dog phone calls, Bourbon-fueled declarations, Christian dating sites, five potential dates, a little revenge dating, and Kerri discovering that apparently being fed a Caesar salad across a table is enough to completely destroy her ability to “play it cool.”

But underneath all the comedy is a bigger question: why can smart, grown women still be drawn to the push-pull energy of a “bad boy”? And what happens when chemistry is incredible but compatibility is… questionable?

Kerri Pomarolli and Suze get honest about dating after divorce, Christian dating, attraction, boundaries, Gen X romance, dating apps, emotional attachment, and what it feels like to start catching feelings when your brain is screaming, “Girl, you know better.”

And this story is only PART 1. To be continued…

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Apparently, being over 50 does NOT mean Kerri has outgrown bad-boy energy. In Part 1 of this very late-night episode of We Might Get in Trouble for This, Kerri and Suze unpack a whirlwind dating situation involving chemistry, Christian dating, boundaries, jealousy, dating apps, and one very complicated crush.

Kerri catches Suze up on what has happened since the last episode — including her ongoing friendship with the Orange County guy, the mysterious “Cheffy,” and how two weeks of dating somehow turned into what feels like an entire year of romance.

There are puppy-dog phone calls, Bourbon-fueled declarations, Christian dating sites, five potential dates, a little revenge dating, and Kerri discovering that apparently being fed a Caesar salad across a table is enough to completely destroy her ability to “play it cool.”

But underneath all the comedy is a bigger question: why can smart, grown women still be drawn to the push-pull energy of a “bad boy”? And what happens when chemistry is incredible but compatibility is… questionable?

Kerri Pomarolli and Suze get honest about dating after divorce, Christian dating, attraction, boundaries, Gen X romance, dating apps, emotional attachment, and what it feels like to start catching feelings when your brain is screaming, “Girl, you know better.”

And this story is only PART 1. To be continued…

Follow We Might Get in Trouble for This:

Instagram: @wemightgetintroubleforthispod

Facebook: @wemightgetintroubleforthispodcast

Watch full episodes at:

https://www.youtube.com/@WeMightGetinTroubleforThisPod

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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?

Send us Fan Mail

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”?