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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.
Follow We Might Get in Trouble for This:

Instagram: @wemightgetintroubleforthispod
Facebook: @wemightgetintroubleforthispodcast
Watch full episodes at:
https://www.youtube.com/@WeMightGetinTroubleforThisPod

Send us Fan Mail

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?