HELP! I Suck at Dating

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 cameras are on and what it was REALLY like to film The Bachelor.   Plus, they revisit their old Bachelor questionnaires from the casting process and you won’t believe some of their answers! See omnystudio...

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.  Plus, find out why Jared thinks Ashley "settled" with him.  See omnystudio.com/listener for privacy information.

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 privacy information.

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 REALLY happened.   Plus, Jenna helps dish out some much needed relationship advice to members of #SuckArmy! See omnystudio.com/listener for privacy information.

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/listener for privacy information.

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 the top dating trends heading into 2023, and Jared opens up about THAT scene from The White Lotus. See omnystudio.com/listener for privacy information.

Deandra Kanu is back with Dean and Jared to help #SuckArmy with their dating questions!  See omnystudio.com/listener for privacy information.

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 some BIG plans for his wedding to Caelynn but… they involve a saxophone. Should he do it?? See omnystudio.com/listener for privacy information.

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 first move.   Plus… what ACTUALLY qualifies as a “date”?? See omnystudio.com/listener for privacy information.

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 information.

Kendall Long from Arie’s season is back with Dean and Jared to share some BIG news! Find out where in the world her new relationship is taking her!   Kendall helps us break down Pete Davidson’s dating history and try to figure out why he’s so alluring.   And, we have to ask her what she thinks about her ex Grocery Store Joe and his recent wedding 👀 See omnystudio.com/listener for privacy informat...

Lexi Buchanan from Peter Weber's season is back with Dean and Jared to help #SuckArmy with their relationship troubles! See omnystudio.com/listener for privacy information.

Lexi Buchanan from Peter Weber's season has landed with Jared and Dean to get into some spicy relationship topics! We get an update on her dating life since being on The Bachelor and how a love interest from before the show has re-entered her life!  And, we come up with a plan for how to gently push your man into a proposal mindset.  See omnystudio.com/listener for privacy information.

Jared is solo working the phones at the Sucky Daters Tipline to help members of #SuckArmy with their dating problems! See omnystudio.com/listener for privacy information.

Now that we’ve heard the story of Dean’s proposal after a treacherous hike, it’s time for Caelynn’s side of the story.   Did she expect a proposal after the lost ring?? What are their plans for marriage and starting a family?? Will Caelynn still propose to Dean??   All these questions and more will be answered in this unfiltered Help I Suck at Dating! See omnystudio.com/listener for privacy inform...

Olivia Caridi from Ben Higgins' season teams up with Jared to help #SuckArmy with their dating troubles! See omnystudio.com/listener for privacy information.

While Dean basks in post-engagement bliss, Jared catches up with Olivia Caridi from Ben Higgins’ season!  Olivia shares her routine of going on at least 2 dates a week to try and get herself out there. She gets real about what its like to date in New York City and how it’s possible to have too much of a good thing.   Plus, we find out if she’ll ever return to the Bachelor franchise! See omnystudio...

It finally happened! Dean is back from his exotic proposal to Caelynn and he’s ready to share all the magic, all the tears, and every intimate detail of how he popped the question! See omnystudio.com/listener for privacy information.

Leah Block from Ben Higgins’ season is back with Dean and Jared to help members of #SuckArmy with their dating problems! See omnystudio.com/listener for privacy information.

Dean is getting ready to pop a BIG question.. if he can find the ring! Dean and Jared are hanging out with Leah Block from Ben Higgins' season and we're hearing all about Dean's proposal plans (or lack thereof).  Plus, Leah shares why she knows her own engagement might be coming soon, and how you can spot similar signs in your relationship!  See omnystudio.com/listener for privacy information.

Dean and Jared are sharing their (somewhat) expertise in the world of dating to help members of #SuckArmy with their relationship issues! See omnystudio.com/listener for privacy information.

Magi Tareke from Matt James' season is here to help Dean and Jared find the secrets to sucking less at dating.  We try to figure out the success rate of arranged marriages, why Instagram is the best dating app, and Dean shares some skydiving tips because sometimes dating feels like a free fall.  See omnystudio.com/listener for privacy information.