HELP! I Suck at Dating

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Latest Episodes:

Deck the Halls with Q&As Dec 11, 2023

Show notes

It’s the holiday season and Jared is up on the ladder putting up the lights! Jared and Ashley are taking over the podcast while Dean and Caelynn are on their honeymoon with a holiday edition Q&A!
Nothing is off limits and secrets get revealed!

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Generation Gap Dec 04, 2023

Show notes

Dean, Caelynn and Jared are in the middle of the great debate of Millenials vs Gen Z vs Gen Alpha! Will Gen Z save the world?? Dean isn’t convinced…

We get an update on Dean and Caelynn’s big move, and Jared lets us in on a “Santa dilemma” when it comes to parenting.

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Talking Turkey (or Salmon) Nov 27, 2023

Show notes

Dean and Caelynn are about to make a MAJOR life change and it could involve little ones sooner than we thought!
Jared and Ashley are preparing for a big move… but Jared is hesitant. Find out how they’re making it work.
Plus, Jared reveals why his biggest goal this holiday season is to make Ashley cry.

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Fantasy Fails Nov 20, 2023

Show notes

Dean is suffering from a major leg injury, and one of our favorite superstars from Bachelor Nation might be to blame!
Jared lost at Fantasy Football… so now it’s time to pick his punishment! You won’t believe what Dean is going to make him do.
Plus, Dean has a shocking surprise to reveal that has everyone split… even Caelynn!

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Sympathy Pains Nov 13, 2023

Show notes

Jared has a full recap from his weekend at Chris Harrison's wedding! Hear what really happened when Kaitlyn Bristowe and Jason Tartick reunited after their split.
We get an update on Dean and Caelynn's next big step after getting married, and Caelynn reveals why Dean's excruciating leg injury might help on his path to become a father.

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Mind the (Age) Gap Nov 06, 2023

Show notes

How big is TOO big of an age gap in dating?? Dean reveals what happened when he dated an older woman when he was in his early twenties!
Sharing your location with your significant other can be a sensitive subject in a relationship, and we hear about how Dean got caught by Caelynn thanks to his GPS.
Plus, Jared opens up about the hidden challenges of trick or treating with a toddler!

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Couples Retreat Oct 30, 2023

Show notes

Dean and Caelynn are on their first couples trip as husband and wife! Hear how things are going on their Hawaiian getaway with Ben Higgins and his wife Jess!

Jared, Dean and Caelynn have all found love in Paradise, but they have some harsh truths to share about the state of things this season on BIP… and nothing is off limits!

Plus, are you team Sophie or Team Priyanka?? You don’t need to a be a JoBros fan to have strong opinions on this debate!

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The Good, The Bad and The Ick Oct 23, 2023

Show notes

What’s your biggest ick?? Dean, Caelynn and Jared reveal their biggest red flags, dealbreakers and icks from when they were dating.
We do a 1 month marriage check-in with Dean and Caelynn, and things get a little TOO real.
Plus, find out the reality show that might bring Dean back to your TV!

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Father of Two Oct 16, 2023

Show notes

Jared and Ashley are officially trying for their second baby! Jared gets a little too real about the positives and negatives of the process…

Dean has some suggestions on how to “influence” the gender of Jared’s second child.

And, Dean opens up about his desire to become a cop! You’ll never guess why…

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The Afterparty Oct 09, 2023

Show notes

Jared is back to give his HONEST take on Dean and Caelynn’s wedding! Hear the good… and the bad from Jared, and why he was worried sick on the way to the ceremony!
Dean and Caelynn had their “brains scanned”… find out what that means and why it might affect where they move to raise a family.
Plus, we hear about a MAJOR life change Dean made after the wedding was over!

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