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HELP! I Suck at Dating - Podcast

HELP! I Suck at Dating

HELP! I Suck at Dating

Society & Culture Tv & Film Health & Fitness Relationships Sexuality
Update frequency
every 2 days
Average duration
45 minutes
Episodes
590
Years Active
2017 - 2025
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The Tux Stops Here

The Tux Stops Here

Dean’s Bachelor party is coming up, but he wants to cancel the entire thing! Find out what gave Dean cold feet about the whole affair.
 
Caelynn gives us a day by day breakdown of her dream Bachelorett…

00:42:51  |   Mon 21 Aug 2023
Inviting the Intrusive Thoughts

Inviting the Intrusive Thoughts

The Newlyweds are ready to reveal some deep dark secrets with a game of “Would You Rather”, and you won’t believe what happened between Dean and Caelynn’s grandparents!
 
Dean and Jared hint at what yo…

00:26:10  |   Thu 17 Aug 2023
Caelynn the Bachelorette

Caelynn the Bachelorette

Caelynn’s Bachelorette party is here and she’s sharing all the secrets behind her big weekend!
 
Is it EVER acceptable to break up with someone over the phone?? Turns out a couple of our Newlyweds migh…

00:41:57  |   Mon 14 Aug 2023
Ask a Newlywed: Be Careful Who You Follow

Ask a Newlywed: Be Careful Who You Follow

Dean, Caelynn and Jared are taking YOUR dating questions and serving up the honest truth. 

What do you do when your partner is following too many models on Instagram?
 
And should you be worried if you…

00:32:01  |   Thu 10 Aug 2023
Reclaiming the V Card

Reclaiming the V Card

Contrary to what you may think, it’s NOT that common for newlyweds to have sex on their wedding night, but Dean and Caelynn might take things to an entirely new level.
 
Dean has a surprising reaction …

00:40:26  |   Mon 07 Aug 2023
Handling Hotness with Elys Hutchinson

Handling Hotness with Elys Hutchinson

Elys Hutchinson from “Too Hot to Handle” hangs out with the Newlyweds for the REAL story of what goes down on the show.
 
Dean and Caelynn ask the hard hitting question… is everyone really THAT horny??…

00:21:58  |   Thu 03 Aug 2023
Love You vs I Love You

Love You vs I Love You

We’re in the final month before Dean and Caelynn’s wedding… but Dean is missing a CRUCIAL detail. Will the whole day be ruined??

We get a front row seat to a major disagreement Dean and Caelynn have …

00:38:01  |   Mon 31 Jul 2023
Influencing the Influencers with Ashleigh Warren

Influencing the Influencers with Ashleigh Warren

Ashleigh Warren from Swiping America is hanging out with the Newlyweds to share her experience of finding love through dating apps and reality TV!
 
Ashleigh has an unbelievable tip on which dating pla…

00:35:28  |   Thu 27 Jul 2023
Baby One More Time

Baby One More Time

Caelynn and Dean have some big news about growing their family!
 
While giving Dean some parenting advice, Jared faces a difficult decision as a father.
 
Plus, Jared shares a secret tip that ALL single …

00:26:11  |   Mon 24 Jul 2023
The Honeymoon Dilemma with Joe Amabile and Serena Pitt

The Honeymoon Dilemma with Joe Amabile and Serena Pitt

The Newlyweds are hanging out with soon to be newlyweds Joe Amabile and Serena Pitt! They’re in the depths of wedding planning and they need some help…
 
Joe spills everything about how he snuck into a…

00:29:02  |   Thu 20 Jul 2023
Shower: Impossible – Dean Reckoning

Shower: Impossible – Dean Reckoning

Caelynn has a harsh truth to share about Dean’s… personal choices. Find out why this could totally change their relationship before they walk down the aisle!
 
Jared shares the unbelievable story of ho…

00:29:59  |   Mon 17 Jul 2023
Give Me Your Heart, Make it Real with Rob Thomas

Give Me Your Heart, Make it Real with Rob Thomas

Jared has re-entered the honeymoon phase with his new bromance! His idol Rob Thomas from Matchbox Twenty joins the Newlyweds to share some incredible advice from his 25 year marriage!

Jared reveals t…

00:50:54  |   Mon 10 Jul 2023
Happy Fourth of July!

Happy Fourth of July!

See omnystudio.com/listener for privacy information.

00:15:07  |   Mon 03 Jul 2023
Tossing the Q&A Bouquet

Tossing the Q&A Bouquet

The Newlyweds are back for another round of Q&A and NOTHING is off limits! Things get tense when Dean admits why he never felt like he was “in love” until recently!
 
Caelynn reveals how she manifested…

00:25:19  |   Thu 29 Jun 2023
For Whom the Bell Tolls

For Whom the Bell Tolls

Dean and Caelynn fill us in on a MAJOR life decision they made at 3 AM in Bali… and Jared doesn’t know how to react.
 
Jared opens up about a frustrating parent moment while trying to build a bike for …

00:36:27  |   Tue 27 Jun 2023
90 Day Mountain Climbing Fiancé

90 Day Mountain Climbing Fiancé

The final countdown is on for Dean and Caelynn’s wedding, and Dean is hard at work to prove there ain’t no mountain high enough to keep him from Caelynn. 

The Newlyweds are answering all your questio…

00:33:53  |   Thu 22 Jun 2023
No Use Crying Over Spilt Paint

No Use Crying Over Spilt Paint

It’s Caelynn’s birthday! And no better way to celebrate than traveling with Dean for 20 HOURS. Will this trip be the final straw for Dean and Caelynn?? We’ll find out!
 
Jared reveals that he and Ashle…

00:29:59  |   Mon 19 Jun 2023
A Tik Tok Marriage with Taylor & Sophia Watts

A Tik Tok Marriage with Taylor & Sophia Watts

Social media sensations Taylor and Sophia Watts join the Newlyweds to talk all about getting married at a young age, sharing everything about their relationship on social media, and what happened whe…

00:23:53  |   Thu 15 Jun 2023
Venue Vendetta

Venue Vendetta

Dean and Caelynn had a photoshoot at their wedding venue! You won’t believe the feelings that came up as they get closer to the big day.

If you’re planning a wedding, you HAVE to hear the method Dean…

00:34:22  |   Mon 12 Jun 2023
The Perfect Date

The Perfect Date

There's some tension between Dean and Caelynn on their wedding date! You won't believe Caelynn's reaction when she finds out when Dean plans on celebrating their anniversary! 

We get a sneak peek at …

00:46:11  |   Mon 05 Jun 2023
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