HELP! I Suck at Dating

Copyright: 2024 iHeartMedia, Inc. © Any use of this intellectual property for text and data mining or computational analysis including as training material for artificial intelligence systems is strictly prohibited without express written consent from iHeartMedia

Latest Episodes:

Three's Company Apr 05, 2021

Show notes

Is a throuple right for you?? Dean and Jared talk to a real life throuple and find out how they make it work! You may be surprised by the insightful relationship tips you will learn from these "Three Dads and a Baby".

On another note, Jared reveals the one weird item Ashley kept from her time on The Bachelor and Dean has a new way to gross out everyone with a shocking reveal of his daily hygiene routine.

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Twin Flames Mar 29, 2021

Show notes

Dean shares a major difference he has with Caelynn and how it affects their relationship.

Jared reveals that he could have ended up with Carly Waddell instead of Ashley!

And find out that Dean’s true soul mate might actually be…. Jared!

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Living in a Rom-Com Mar 22, 2021

Show notes

Dean and Jared talk to screenwriter Tiffany Paulsen about how to find real life relationship advice from romantic comedies.

Find out the major breakthrough Dean made with his brother over his relationship with Caelynn!

And Caelynn joins to clear things up about “the cabana story”.

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Lending a Hand Mar 15, 2021

Show notes

Jared reveals what’s really going on with Nick Viall’s new relationship. Could she be “the one”??

Is it true that the longer you’re in a relationship, the less sex you have? Dean and Jared share their experience.

And find out what causes the biggest fights between Jared & Ashley and Dean & Caelynn!

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

A Touch of Lace Mar 08, 2021

Show notes

Dean and Jared catch up with Lace Morris from Ben’s season of The Bachelor, and find out the dangers of matching tattoos.

Plus, Dean tells the story of how he almost broke up with Caelynn

And Jared opens up about being on the brink of divorce!

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Touchdown Pass Mar 01, 2021

Show notes

Jared opens up about his journey to parenthood and hears some fatherly advice from NFL great Matthew Judon about how to “throw a game winning pass”.

Matthew answers everything you want to know about the mind of a man for a round of “Ask a Guy”.

And we catch up with Liz Sando from Nick Viall’s season (as she’s about to deliver a baby!)

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

No Filter No Cry Feb 22, 2021

Show notes

Is it possible to go on a truly blind date anymore?? Dean and Jared talk to Alex Durrant, founder of the Jigsaw dating app, about how his app is saving singles from superficial dating.

Hear about Dean’s catfish close call.

And, Dean reveals a broken promise from Caelynn that changed him forever.

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Thirty, Flirty & Thriving Feb 15, 2021

Show notes

Dean and Jared hear some crucial dating advice from the hosts of the Almost 30 podcast about how relationships can DRAMATICALLY change from 25 to 30!

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Mensches & Schmucks Feb 08, 2021

Show notes

Dean spills on his wedding with Caelynn and if we’ll see them tie the knot on TV!

We find out how Ashley’s parents reacted when they first met Jared

Plus, hear some crucial advice on how to find a “mensch” in your city!

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.

Open Ended Questions Feb 01, 2021

Show notes

Dean opens up about being in an open relationship!

Jared tries to figure out if Ashley is more obsessed with him than he is with her.

And, we talk to psychologist and relationship expert Guy Winch about how to tell that a couple is going to break up after spending 90 seconds with them.

Learn more about your ad-choices at https://www.iheartpodcastnetwork.com

See omnystudio.com/listener for privacy information.