HELP! I Suck at Dating

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Latest Episodes:

Caelynn’s Corner: Searching for Kate Mar 14, 2024

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Caelynn and Dean are diving deep into their latest pop culture obsessions! We hear all their hot takes from the Academy Awards, including the best and worst dressed!

And… Caelynn shares everything she knows about the ongoing mystery of Kate Middleton!

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Been There, Dean That: Havin a Ball in Havasupai Mar 13, 2024

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Ever wonder where you can find the most amazing waterfall in the USA? Dean is ready to reveal all of his secrets about traveling to Havasupai in Arizona!

Dean and Caelynn reveal some crucial hiking do’s and don’ts, and they tell you the real story on what is and isn’t worth the money.

Plus, find out if Dean was brave enough to jump off a 100 foot waterfall!

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Need Some “Me Time” Mar 11, 2024

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Is it okay to want “alone time” away from your partner or children?? Jared is struggling with his desire for solitude and Dean and Caelynn realize they’re less codependent than they thought!

We get a trip update from Dean and Caelynn’s latest international adventure, and find out which Bachelor alum has all 3 Suckers cringing with their social media content!

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Caelynn’s Corner: Bachelor Obsessions Mar 08, 2024

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Caelynn and Dean are diving into the latest pop culture news! Hannah Brown is writing a romance novel and it might inspire Caelynn to do the same, but with more dragons and post-apocalyptic vibes.

How do Dean and Caelynn feel about Kristin Cavallari’s new (and much younger) boyfriend!

And, why do we love celebrities without perfect teeth??

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Been There, Dean That: The Bad Trip Mar 06, 2024

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Traveling can open your mind, create lasting memories, and bring you closer to your fellow human… but what happens when everything goes wrong??

Dean and Caelynn relive their trip to St. Lucia that they planned after only a few months of dating!

Come brave the rainforest, poisonous snakes and more while we find out what to do on a terrible vacation!

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You’re On Mute Mar 04, 2024

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Let’s be honest… how many people have you “muted” on social media?? Dean, Caelynn and Jared spill about which members of Bachelor Nation they have muted on Instagram and you’ll be shocked at who made the list!

Jared’s officially going to be a father to 2 boys! We brainstorm some potential names for Dawson’s younger brother.

Plus, Jared makes a small change on his Instagram that could spark some “divorce” headlines for him and Ashley!

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Talk Daddy to Me: Boys 2 Men Mar 02, 2024

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Jared has announced the gender of baby #2! But he feels a bit conflicted about being a dad to two boys.

Hear his concerns, hopes and wishes as he prepares for his new son, and we find out why they might be making a BIG move as a family of four.

Plus, how do you find time for yourself when you’re a parent??

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Caelynn’s Corner: Keeping Up with The Cyruses Mar 01, 2024

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Caelynn has a pop culture round-up and breaking down all the family drama going on with the Cyruses! Find out everything going on with Tish, Noah and Billy Ray Cyrus.

Dean and Caelynn discuss their favorite celebrity couples and reveal which superstar they’d allow to sign their forehead.

Plus, Dean opens up about the popular show that he just can’t stand!

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Been There, Dean That: Guatemala Feb 28, 2024

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Dean and Caelynn take us through their trip to Guatemala! Find out which cities to visit, travel tips once you get there (don't lose your water bottle), and how to stay safe when traveling abroad!

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A Bunch of Baloney Feb 26, 2024

Show notes

Jared and Dean both open up about family struggles this week, with Dean sharing his strained relationship with his father, and Jared admitting that sometimes he's bad at keeping the romance alive with Ashley.
Dean and Caelynn have a house renovation update, and we hear the frightening true fact that might stop you from picking your nose!

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