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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.

Follow We Might Get in Trouble for This:

Instagram: @wemightgetintroubleforthispod

Facebook: @wemightgetintroubleforthispodcast

Watch full episodes at:

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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…

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

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