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.
Feb 07, 2022•35 min
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.
Feb 02, 2022•20 min
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.com See omnystudio.com/listener for privacy information....
Jan 31, 2022•41 min
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/listener for privacy information....
Jan 27, 2022•27 min
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 omnystudio.com/listener for privacy information....
Jan 24, 2022•45 min
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.
Jan 17, 2022•1 hr 1 min
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! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for...
Jan 10, 2022•51 min
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 dilemmas. Plus, could Kelley be your next Bachelorette?? Learn more about your ad-choices at https://...
Jan 03, 2022•58 min
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 for you! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/li...
Dec 20, 2021•51 min
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.com/listener for privacy information....
Dec 13, 2021•1 hr
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.
Dec 06, 2021•45 min
A number of Bachelor couples have broken up recently… so Dean and Jared are trying to figure out why! Which Bachelor show has the most “success stories”? And what do these predictions mean for the future of Dean and Caelynn?? We take a trip through the past to find out who in Bachelor Nation sucks at dating! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Nov 29, 2021•59 min
Now that Dean and Jared are back from Ben’s wedding, everyone wants to know when Dean is tying the knot! What would Dean say if… Caelynn proposed to him?? Something might be in the works… And to ring in the holiday season, we hang with Amanda and Markelle from HBO Max’s “12 Dates of Christmas”. This dating show is MUCH different than The Bachelor, and we find out everything that goes down! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for pr...
Nov 22, 2021•50 min
Dean shares all the buzz in Nashville for Ben Higgins’ wedding! Find out what’s going through his mind just before he walks down the aisle! Vanessa Anoorsian and Natasha Khachatoorian from “The Armenian Dating Show” tell us about the experience of including their ENTIRE family when it comes to picking a guy. And Dean reveals his awkward blind date story! Plus, what do you do when you run into past hook-ups with your new partner?? Learn more about your ad-choices at https://www.iheartpodcastnetwo...
Nov 15, 2021•42 min
Dean and Jared talk to Leigh Isaacson, founder of Tabby and Dig. And in case you’re not a pet person, those are dating apps for cat lovers and their canine loving counterparts. Find out what you can learn about a potential partner through their pets! And Leigh reveals the app’s strange connection to a recently single Bachelorette! Plus, Dean opens up about a Caelynn’s battle with a home intruder! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener...
Nov 08, 2021•1 hr 4 min
Dean gets real about everything else he’s sucked at… besides dating. And he reveals some of his biggest challenges with Caelynn! We get to know the stars of Prime Video's “Tampa Baes” and learn how crazy things can get when you forget the cameras are rolling. Plus, when should you put your partner’s priorities above your own?? Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Nov 01, 2021•41 min
Are you overwhelmed with online dating? Not sure which apps to join, how many pictures to post? Dean and Jared know how you feel, so they’ve brought in dating expert Alyssa Dineen to help clear up some of the biggest challenges in dating apps! Plus, Dean and Jared share some advice on how to reignite the spark in your relationship if your partner is too focused on work. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Oct 25, 2021•47 min
Dean and Jared connect with Amie Yudice, who is a “woman in transition”. She shares her experience of starting a new era of her life post-divorce, with some crucial tips to get back in the dating game. Dean opens up about how he handled break-ups during his “f-boy days”. And find out how you can get top secret Bachelor dating advice by visiting Jared and Ashley’s coffee shop! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy informat...
Oct 18, 2021•1 hr 3 min
Now that we’ve all seen Dean and Caelynn’s big moment on Paradise, we have to hear the REAL story of what almost went down on the beach. Dean is ready to tell all, and because it’s Dean, he’s not holding anything back. And, Dean and Jared talk to a married couple that are re-inventing their lives after their kids moved out of the house, and putting it all on YouTube. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Oct 11, 2021•56 min
Dean reveals that his overseas trip may have been more than just a vacation! Find out what this means for his future with Caelynn! Jared drops a few hints about his new coffee shop that will make Bachelor Nation fans VERY happy. And, Dean opens up about his near death experience in Alaska. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Oct 04, 2021•59 min
Fresh off the beach (and back in clothes), Jared hangs out with Britt Whitmire from “Naked and Afraid of Love”! She shares her experience dating completely naked, and why it might be a more effective method than The Bachelor! And we get an inside look at Jared & Ashley’s coffee shop as they prepare to open the doors! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Sep 27, 2021•46 min
Dean and Jared share a much needed breakdown of this season of Bachelor in Paradise. You won’t believe the scorching hot takes these Paradise alumni have to share! Has Covid made you unmotivated to work out?? Dean is feeling it and opens up about how his workout routine is much different than Caelynn’s these days. Plus, Hannah Berner from Summer House on Bravo stops by and spills everything about why she left the show! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See ...
Sep 20, 2021•1 hr 15 min
Dean sets the record straight on his marriage and reveals a shocking discovery about Caelynn since they’ve been overseas. Jared and Dean answer all your questions in a raw unfiltered Q&A! And because it’s late at night where Dean is… his answers are spicy! Plus, Jared shares what scares him most about becoming a father. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Sep 13, 2021•49 min
Jared's wife Ashley I joins Dean and Jared to find out what really happened on “F-Boy Island”! Casey Johnson tells us the story of how he arrived as an F-Boy and left a “reformed nice guy”. Fernando Titus shares some behind the scenes drama from making the show and why he thinks nice guys finish last. And, Dean might be on his honeymoon??? Dean might be the best F-boy success story! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy i...
Sep 06, 2021•49 min
We finally know what gender Jared and Ashley are expecting! But the next secret for us to guess is the name of their baby. It’s something Ashley has had picked out for over 20 years! Dean and Jared answer all your questions about dating, relationships and beyond. Dean reveals that in the past, he’s been “bad at break-ups”. What does this mean?? And is a FaceTime break-up ever acceptable?? When are you allowed to have “the talk” without meeting face to face? Learn more about your ad-choices at ht...
Aug 30, 2021•59 min
Jared is back from Ashley’s first ultrasound and the reality of fatherhood is setting in. There’s one big question on everyone’s mind about the bundle of joy and Jared is ready to reveal! Paulina and Mike from Shahs of Sunset had a very different reality show experience than Dean and Jared and they’re here to set the record straight. What do you do when your friends don’t approve of you’re new partner?? Mike and Paulina went through that challenge with cameras rolling! Learn more about your ad-c...
Aug 23, 2021•57 min
Dean and Jared need some spousal support! Caelynn and Ashley join their other halves to reveal some major secrets! Find out why Caelynn won’t become the new “Mrs. Unglert”. Jared and Caelynn confront Dean about an issues that affects everyone close to him. Plus, Dean and Jared share their honest thoughts on how things ended with Katie and Greg on The Bachelorette! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Aug 16, 2021•52 min
Dean and Jared are taking a (virtual) trip to Love Island! Find out why even on Love Island, people still suck at dating. We check in with some of the contestants, and hear from Cinco who tells us what really went down between him and Cashay. Contestant Javonny reveals the first thing he did when he got voted off (and it involves clippers!) And Love Island host Arielle opens up about the pressure of the show airing (almost) live. Love Island fans, this one is for you! Learn more about your ad-ch...
Aug 12, 2021•55 min
How can you tell you’re in a toxic relationship?? Dean and Jared have some tips on how to spot toxic traits in your partner. If Kristina Schulman wrote a tell-all book… would she mention Dean? And can you be friends with an ex… if it’s not YOUR ex?? Hopefully Dean can share some wisdom before he misses another flight! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Jul 31, 2021•58 min
What are you supposed to do on a first date?? The eternal question. Jared shares some helpful tips to make your next first date memorable! Relationship coach Dr. Nicole LaBeach reveals the signs to know you’re in a healthy relationship. This is CRUCIAL information if you’re dating someone new! And find out how to prepare your partner before having a tough conversation. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information....
Jul 26, 2021•58 min