HELP! I Suck at Dating

Both Jared and Dean found love while in a swimsuit in Paradise, but could they handle a dating show where you truly bare all?  You’ll be shocked to hear what Dean and Jared think of the UK show “Naked Attraction”, and find out how to make a lasting first impression with your clothes ON.  Plus, Dean reveals why he might get rid of his wedding ring! Learn more about your ad-choices at https://www.ih...

Sierra Jackson is back with Dean and Jared to break down all the questions that come with a marriage proposal! We’re hanging out with Rebecca Lynn Pope, host of “Marry Me Now” on OWN, and she shares some insight on how to know when your partner is ready for the big question.  And Dean opens up about how he would react if Caelynn got down on one knee and asked HIM to marry her!   Learn more about y...

Sierra Jackson from Clayton's season of The Bachelor joins Dean and Jared to try and figure out which of the new emojis are best for sending a spicy text!  Sierra shares some of the red flags she got from Clayton that you DIDN'T see on The Bachelor.  And find out who she's hoping to see in Paradise!  Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listen...

Abigail Heringer from Matt James’ season is back with Dean and Jared to ask the million dollar question: Can you find love on “Joe Millionaire”?? Steven and Calah from Joe Millionaire are here with the honest truth about how things are going in their relationship since the show ended! We hear the latest on their engagement and they fill us in on what it means to get a “promise ring” put on your fi...

Dean and Jared hang out with Abigail Heringer from Matt James' season, and she has some exciting dating news to share! She has all the details on how she and Noah became a Paradise success story and she opens up about why it was eye opening to watch the season back.  And we go through the 8 Break-Up "Dos and Don'ts". If you've recently broken up, you need to hear this list!! Learn more about your...

We're OBSESSED with Love is Blind on Netflix so Jared, Dean and special guest cohost Heather Martin are hanging out with one of the success stories from season 1: Lauren Speed-Hamilton! Lauren lets us in on her relationship with Cameron and how their family might be growing soon! But she also shares some of the hottest and dramatic moments that went on behind the scenes of Love is Blind.  And Jare...

Heather Martin from Colton’s season is sitting in with Dean and Jared this week! She gives us an update on her dating life after crashing Matt James season of The Bachelor, and we try to figure out what’s worse: breaking up with someone, or getting broken up with! And… does Dean have “baby fever”?? We clear things up and get the real answer! Learn more about your ad-choices at https://www.iheartpo...

Are you uncomfortable talking about sex? Jared, Caelynn join Caroline Lunny from Arie’s season to discuss everything you’ve wanted to know about sex… but were afraid to ask. They’re sitting down with intimacy educator and author Shan Boodram to try and uncover why there’s so much shame and secrecy around sex.  Shan gives Caroline some life changing advice after she shares a very personal moment. ...

Caroline Lunny from Arie's season joins Jared and Caelynn for a real and honest conversation about becoming a parent, as Caroline lets us in on her journey of freezing her eggs.  Jared gives us the REAL truth about being a first time parent and Caelynn reveals the deadline she gave for Dean if he wants to be a dad! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnyst...

Do you know which fork to use at a fancy dinner? How to ask for a raise? How to decipher a thirst trap?? All these questions and more are answered when Dean, Jared and guest co-host Sydney Lotuaco talk to the “Duchess of Decorum”! We’re hanging out with Pattie Ehsaei who went viral on Tik Tok teaching young people how to navigate through situations no one prepared us for!   Plus, find out why Dean...

Sydney Lotuaco is back with Dean and Jared and she has some exciting news... she's engaged!  Jared shares some crucial wedding planning advice and we hear how Sydney plans on working her pro dancer background into the ceremony!  Plus, find out why a major celebrity break-up could be very good news for Dean.  Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.co...

Would you set your mom up on a date?? Dean, Jared and Annaliese Puccini talk to Karen Larrera and her daughter Breana from "My Mom, Your Dad" on HBO Max.  We find out if kids can REALLY make better dating decisions for their parents, and how Karen's experience on the show is different from The Bachelor.  Plus, what should you do if you suspect infidelity from your in-laws?? Learn more about your a...

Annaliese from Arie's season of The Bachelor is back and hanging out with Dean and Jared! Kurt Sowers (AKA Joe Millionaire) tells us his experience dating on reality TV, and why it might be more effective than The Bachelor.  And, Kurt reveals his surprise romance that didn't involve a contestant! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener f...

Jared’s off adjusting to new dad life, but Caelynn is back to help Dean pick up some tips for first time parents!  Dawn Dias shares all the “sh*t they never tell you about parenting” along with some incredible advice on how to split up the duties when a new baby joins the family.  Plus, Dean and Caelynn reveal their plans for kids… both with and without fur! Learn more about your ad-choices at htt...

Dean and Caelynn are baring all and answering some of the toughest relationship questions with TOTAL honesty! Everything is on the line when we ask about their future together, their biggest relationship challenges and who does the cooking!   Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

We’re catching up with Jared just hours after becoming a new father! Find out everything that happened in the delivery room and why he’s afraid he’ll “suck” at being a dad. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

Annaliese from Arie’s season is back from Hawaii and is ready to share all her dating stories with Dean and Jared!  Jared could be mere HOURS away from becoming a father and shares his most personal thoughts.  Dean has a “crush” on Caelynn, but it might not go other way…  And, find out if Annaliese would return to The Bachelor! Learn more about your ad-choices at https://www.iheartpodcastnetwork.c...

Angela Amezcua is back with Dean and Jared to get some much needed relationship advice from matchmaker Jackie Dorman!  Find out why it’s BETTER for a relationship to move fast! Would you get married after dating for less than 12 months?? And we learn that the pandemic could lead to a “marriage boom”. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listen...

Angela Amezcua from Nick’s season and Bachelor in Paradise is back with Dean & Jared! She’s ready to spill everything about her new relationship after leaving BIP: Canada and she reveals why Paradise couples have a much higher success rate! Plus, what is “outer-course” and why is it considered the “future of dating”?? Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See...

Fan favorite Kendall Long is back with Dean and Jared! She gets real about her experience on Paradise and we hear an update on her dating life! And, find out which member of Bachelor Nation Dean is attempting to set up with Kendall!  Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

Kelsey Weier from Peter’s season of The Bachelor and Bachelor in Paradise is hanging out with Dean and Jared this week! She’s moved on from “Champagne-gate” and is ready to spill EVERYTHING about her first kiss since Pilot Pete!  Learn some proper lessons on How to Flirt (it’s all in the eyes) and we get a few crucial Tik Tok Tips from a master of the art form, Brett Robinson from Big Brother! Lea...

Suck Army...we're back and better than ever. This is the new and improved HELP I SUCK AT DATING.  We’re heading into 2022 with a different female co-host each week! Kelley Flanagan is in the HOT SEAT! We get an update on her dating life and she lets us in on what happened in her relationship with Pilot Pete. Now, more than ever, it's time to listen as this crew will help you solve all your dating...

Between starting a new business, buying a house and supporting a very pregnant wife, Jared has zero time for the holidays! What do you do when you feel overwhelmed this time of year??  Dean and Caelynn are split on how to spend Christmas Day. Hear what will happen if they spend the holiday apart!  And, have you ever felt “trapped” in a relationship? Dean and Jared might have some words of wisdom f...

Can a relationship become stronger after going on a “break”?? Dean and Jared discover the truth about taking breaks. Ashley I reveals the biggest challenge in her relationship with Jared and why it might be getting worse. And could filters be ruining your dating life?? Find out if Facetune is a friend or foe! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.c...

 Dean made a major change in his life that might send him back to his “f-boy” days!  Jared shares all the craziness from the opening of his coffee shop! And Dean opens up about the tragic loss of his dog Pappy. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.