HELP! I Suck at Dating

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…

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 pu…

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 succe…

Dean and Jared are joined with Dean’s future wife Caelynn Miller-Keyes as a permanent co-host.

Together learning  the ins and outs of marriage, and there’s no telling what other life lessons they’l…

Courtney Robertson from Ben Flajnik’s season of The Bachelor connects with Jared over something EVERYONE should know before going out on a date: How to be a good tipper! 
 
Courtney opens up about what…

Jill Chin from Clayton's season and BIP is hanging out with Dean and Jared and ready to drop a hard launch... or maybe a soft launch? We try to figure out what exactly it is. 

What is "Bachelor Head"…

Hunter Haag from Clayton’s season and Bachelor in Paradise is getting caught up with Dean and Jared, and telling us everything about dating from the perspective of a REAL Disney princess!
 
She gets re…

Kiarra Norman from Peter Weber's season is back with Dean to help members of #SuckArmy get through some serious dating problems!

See omnystudio.com/listener for privacy information.

Kiarra Norman from Peter Weber’s season is hanging out with Dean and sharing why she thinks she could be next to join the Engaged Club!
 
Dean and Kiarra get real about how people change when the camer…

Dean and Jared are teaming up with Lauren Jones from Peter Weber's season to  help members of #SuckArmy suck less at dating!

See omnystudio.com/listener for privacy information.

Lauren Jones from Peter Weber's season is hanging out with Dean and Jared and sharing EVERYTHING about her dating life. 

Did she miss out by skipping Paradise?? Jared and Dean share the honest truth.…

Happy New Year! Dean and Jared reflect on their holidays, the life lessons they learned in 2022, and Dean shares the trials and tribulations of wedding planning.

See omnystudio.com/listener for privac…

Jenna Cooper from Arie’s season is throwing a holiday party with Dean and Jared!
 
She shares all about her painful experience with Jordan after their time on Paradise and we finally clear up what REAL…

Dean and Jared break down everything about the big Bachelor Nation proposal this week! 

Find out how Caelynn surprised him and what Dean REALLY thinks about the “dual proposals”.

See omnystudio.com/li…

Dean and Jared get real about how red carpet interviews have changed from the time when they were FRESH off The Bachelorette, and Dean admits a major difference between him and Caelynn.
 
We get into t…

Deandra Kanu is back with Dean and Jared to help #SuckArmy with their dating questions! 

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Deandra Kanu from Peter Weber’s season is back with Dean and Jared and ready to share everything about her dating life!

She shares the one thing guys can do to catch her eye in her DMs.

And Dean has …

Shushanna Mkrtychyan from Ben Higgins' season is back with Dean and Jared to help #SuckArmy get better at dating!

See omnystudio.com/listener for privacy information.

Dean and Jared are hanging out with Shushanna Mkrtychyan from Ben Higgins’ season! 

Shushanna and Dean bond over their shared love of rock climbing and we hear about the importance of making the firs…

This year we're thankful for Kendall Long and her dating expertise! She's back with Dean and Jared to help #SuckArmy with their relationship questions!

See omnystudio.com/listener for privacy informat…