HELP! I Suck at Dating

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Latest Episodes:

Bachelor(ette) Parties with Hannah Godwin Mar 30, 2023

Show notes

Dean and Caelynn found kindred spirits in Hannah Godwin and Dylan Barbour who are ALSO in the midst of wedding planning!
Find out where they’re looking to tie the knot… IF Hannah can find a dress in time!
And, will Dean and Caelynn sign a prenup??

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Lifting the Viall with Natalie Joy Mar 27, 2023

Show notes

Did you see Nick Viall’s showstopping proposal?? Dean, Jared and Caelynn are talking to the woman of the hour, Natalie Joy, about her life as a fiancé and soon to be newlywed!
Hear all the details from her fairytale engagement and why Nick had to hire “extras” to make sure the whole thing was a surprise!
Plus, we get an update on wedding planning and why you might see a bundle of Joy in the Viall house before they walk down the aisle!

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A Courthouse Cakewalk with Serena Pitt Mar 20, 2023

Show notes

Dean may have found his dream wedding venue after talking with Serena Pitt about her courthouse marriage to Grocery Store Joe.

Serena shares all the wedding advice with Dean and Caelynn, but Dean only seems interested in his beloved ice cream wedding cake.

Plus, will Dean have a mustache on his big day??

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Lord of the Rings: Return of the Dean Mar 16, 2023

Show notes

Remember when Dean lost a huge diamond engagement ring? Well… he got a replacement, and it doesn’t look like he learned from his mistakes.
Caelynn confronts Dean LIVE on the podcast about some of the challenges that might prevent them from actually becoming “newlyweds”.
Plus, we answer all your relationship emails!

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Say Yes to 2 Dresses with Kenny Braasch and Mari Pepin Mar 13, 2023

Show notes

Dean and Caelynn hang out with the next Bachelor couple to tie the knot: Kenny Braasch and Mari Pepin!
If you think planning 1 wedding is tough… wait until you hear how Kenny and Mari are preparing for 2 weddings!

We get real about Bachelor parties, picking your honeymoon out of a jar, and if you’d want to have a “buddy moon”.
Plus, find out Mari’s biggest issue with Kenny and why it might mean a MAJOR change in their relationship before they get married!

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Popping the Questions! Mar 09, 2023

Show notes

Dean, Caelynn and Jared have some honest answers when #SuckArmy drops to one knee and asks the BIG questions!
Find out why Jared NEVER expected Dean and Caelynn to go the distance!
And, Caelynn reveals the one thing holding her back from pregnancy.

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Twinning with Emily Ferguson Mar 06, 2023

Show notes

Dean, Caelynn and Jared catch up with Emily Ferguson (one of the twins from Ben Higgins’ season) for an update on her new life as a mom to be!
She’s married to a pro hockey player, which is a life that’s surprisingly very similar to the nomad adventurer style of Dean, so she has some advice that will completely change Caelynn’s expectations.
And, Emily shares some unexpected tips on how to make your wedding day memories last forever!

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The Big Snip Feb 27, 2023

Show notes

Dean and Caelynn are nearly 10,000 miles apart right now, and it took a podcast to bring them back together! You’re hearing their first real conversation in 2 weeks since Dean left for Antarctica!
We consult a doctor about Dean’s extreme birth control plan, and why he might not want to get snipped.
Plus, Dean and Jared learn a very valuable lesson about the female anatomy. But better late than never!

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Intimacy Appointments with Jade Roper Tolbert Feb 22, 2023

Show notes

Jared and Caelynn get some marriage advice from one half of one of the biggest Bachelor success stories: Jade Roper Tolbert!
She and Tanner “schedule” sex, but it works! Find out the advantages to putting sex in your calendar like you would for a dentist appointment or soccer practice.
Jade gets real about the good and the bad from her televised wedding, and we find out the MAJOR decision Dean is making about building a family with Caelynn.

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Advice from an OG with Trista Sutter Feb 20, 2023

Show notes

Jared and Caelynn go to legendary Bachelor OG Trista Sutter for some much needed marriage advice!
She shares some wisdom she’s collected from the last 20 years that will help ANYONE have a more successful marriage.
And, we find out why Dean and Caelynn are only speaking once a month… could this be the end of their relationship??

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