HELP! I Suck at Dating

Dean and Jared are hanging out with Raven Gates from Nick Viall’s season and Bachelor in Paradise! She has an update on her love story with Adam Gottschalk and she shares the details from the emotional delivery that gave her a healthy baby.   We discuss Katie Thurston’s current relationship status and the power of taking a moment to “date yourself”.   Plus, Dean and Jared share their biggest perso...

See omnystudio.com/listener for privacy information.

Dean and Jared meet the REAL 40 year old virgin! Tommy Lee shares his story of trying to get laid with the help of his friend, comedian and pro athlete Nem Stankovic.   The friends share that Tommy’s journey to losing his virginity transformed into finding his adulthood and learning confidence and self-esteem.   And, Jared opens up about Ashley’s experience as a virgin at 27 years old. See omnystu...

Caelynn is our special guest co-host this week because she wants to set the record straight on her relationship with Dean!  This is an unfiltered and uncensored look into the realities of their partnership. Find out their biggest challenges and who made the tougher compromise in their lives together!  And, we finally hear the truth about their plans for marriage.  See omnystudio.com/listener for p...

“Queen Victoria” Larson from Matt James’ season is here with Dean and Jared to try and figure out why she sucks at dating.   But first, she has to admit to Ashley why she’s had her blocked since they met on The Bachelor set during her season!   And, Victoria reveals why she took on the role as “the villain”.   See omnystudio.com/listener for privacy information.

Dean and Jared are learning the secret to what makes…or breaks… a relationship from Dr. Nicole LaBeach from OWN’s “Put a Ring on It”.   She’s an expert in determining if a couple will stay together or go their separate ways.   And, find out why you should be worried if you NEVER fight with your partner! See omnystudio.com/listener for privacy informa...

When you come off The Bachelor, it’s not always a fairy tale romance! Dean and Jared discuss the difficult first year that many Bachelor couples face after the show.  Should Dean expect something from Caelynn if he gets her an engagement ring??  Plus, Jared reveals a big change coming in his relationship with Ashley.   See omnystudio.com/listener for privacy information.

Anna Redman from Matt James’ season is back with Dean and Jared for a therapy session with the Shrink Chicks! Emmalee and Jen are best friends that became marriage and sex therapists and now want to pull back the stigma on therapy.   Hear some amazing advice on how to bring up therapy with your partner, when is the best time to seek therapy, and how to get mental health help on a budget...

Jared and Dean catch up with Anna Redman from Matt James’ season! She spills everything about her relationship with Chris Bukowski and we find out when they plan on taking “the next step”!   Plus, Anna shares some brutally honest advice for anyone going to Paradise!   See omnystudio.com/listener for privacy information.

Jared and Dean are hanging out with one of the newest parents from Bachelor Nation: Daniella McBride from Sean Lowe’s season! She had twin boys last year and has some advice for Jared on how to get to the “fun” baby stage.   We hear the status of Daniella’s 7 year relationship and why they haven’t gotten married!   Plus, who should change their name when get...

Pieper James is back with Dean and Jared to hang with Leah McSweeney from The Real Housewives of New York! Leah is a HARDCORE Bachelor fan… but would she ever go on the show?? She has an important lesson to share that she picked up while following Jared and Ashley’s love story. And, find out the ONLY reason (according to Leah) that you should stay in touch with an ex! See omnystudio.c...

Dean and Jared get to know fellow Paradise alum Pieper James! We hear the real story of her controversial romance with Brendan and we find out the truth behind rumors of their break-up.  Hear the good and the bad that comes with a long distance relationship and we get the latest on what's going on between Pieper and Natasha Parker! Plus, Dean reveals a BIG decision that could completely chang...

Dean is back with Sarah Herron and if you thought finding love on The Bachelor was strange, wait until you meet Austin and Paige from “Love in the Jungle” on Discovery+!   We hear all about trying to make a romantic connection by embodying an animal and reenacting mating rituals. Does it work??   What animal would Sarah take on if she was sent to jungle? All is revealed! See...

Dean is going one on one with Bachelor in Paradise OG Sarah Herron (Sean Lowe’s season) for a very special episode! Sarah and Dean have an unexpected connection that goes much deeper than you might think!   Sarah opens up about her journey with IVF and she and Dean reveal why Paradise can sometimes feel like Hell.   Plus, find out why Dean and Caelynn are in a “rut”! Se...

Dean and Jared are back with Katie Morton! We talk to Lisa Bilyeu, cofounder of Quest Nutrition (yes THOSE health bars!) and she shares some incredible advice on how to overcome hardship and achieve success.  If you've ever struggled with confidence, you need to hear this conversation.  And when we needed him most, Love Man returns!  See omnystudio.com/listener for privacy informati...

Katie Morton from Colton’s season is back with Dean and Jared, and she might STILL suck at dating. She’s in a long term and VERY long distance relationship, and she’s ready to give us the real story on dating someone overseas! Find out if she’s going to spend a lot of time in an immigration office OR if we’ll see her back on the beach in Paradise!   See omnystudi...

Jared connects with Tammy Kay Ly from Peter Weber’s season and Bachelor in Paradise to try and figure out dating when you travel between 3 different cities!   Tammy has been all over, so she has firsthand knowledge on dating in LA, NY, and Mimai, all while working 6 jobs!   And how do guys react when a woman approaches THEM? Should women be more proactive in shooting their shot? Se...

Dean and Jared are hanging out with Ben Higgins and Ashley I from the Almost Famous podcast for a special crossover party presented by Pandora Jewelry!   We're putting the spouses in the hot seat! Ashley and Caelynn join in to answer the most intimate questions about Jared and Dean. But Ben isn't safe! We bring in his new wife Jess to get the real story on what it's like to be married to "Per...

Dean is live from a Wyoming mountaintop to try and figure out how to suck less at dating!  Dean opens up about how Caelynn has changed his life and anyone who can smell him is VERY grateful. But it goes both ways, and we find out which of Dean's dirty habits have rubbed off on Caelynn.  And Jared is concerned about baby Dawson's exposure to social media. How do you limit access as parent...

Kendall Long and Deandra Kanu return with Dean to get to the bottom of what people are REALLY looking for in a partner. We talk to the Matchmaking Duo about the secret details that will help you land the person of your dreams! They have 2 IMPORTANT tips that are guaranteed to land you more dates with higher quality people, and we find out the perfect mindset to have when starting to date someone n...

Kendall Long is back with Dean and and she has some BIG news to share about her "hard launch" on Instagram.  And we talk to Deandra Kanu from Peter's season about the challenges of dating in LA. Do apps still work?? See omnystudio.com/listener for privacy information.

If you can’t get enough of “The Ultimatum” on Netflix, you don’t want to miss this episode! Dean and Jared are back with Serena Pitt from Matt James’ season and this time we have Randall and Jake from “The Ultimatum”!   Find out what caught Randall off guard about going on the show, and Jake reveals what changed his mind when he refused to go on. &nbs...

Serena Pitt from Matt James’ season and Bachelor in Paradise joins Dean and Jared to catch up on her romance with Grocery Store Joe! She spills everything about how their relationship has changed since moving to New York together and we find out why they might be getting married sooner than you think!   Plus, Serena tells us the REAL story of why she sent herself home on Matt’s se...

Genevieve Parisi from Clayton’s season is back with Jared to try and figure out dating in 2022 with Jordana Abraham, founder of Betches! Genevieve WISHES she was married and Jordana has some advice on how to find “the one”! Do you think technology has helped or hurt dating?? We try to understand how dating has changed and where its headed in the future. Plus, Jordana is a HUGE Ba...

Genevieve Parisi from Clayton’s season is hanging out with Jared this week and spilling EVERYTHING about her time getting to know the “real” Clayton. Is it possible to see her on the beach in Paradise?? Jared gets Genevieve to open up about her future with the franchise. Plus, we share tips on how to make your long term relationship “flirty” again! Learn more about your ad-choices at https://www.i...