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HELP! I Suck at Dating

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HELP! I Suck at Dating

  • 979 episodes
  • Updated Monday

Episodes979

  • Nov 1, 2021 · 40 min

    Bae Watch

    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.

  • Oct 25, 2021 · 46 min

    Don't Forget to Swipe

    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 18, 2021 · 1 hr 2 min

    Are Relationships a Waste of Time??

    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 information.

  • Oct 11, 2021 · 55 min

    Flew the Coop

    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 4, 2021 · 59 min

    The Caelynn Effect

    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.

  • Sep 27, 2021 · 45 min

    Jared Bares All

    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 20, 2021 · 1 hr 15 min

    Paradise Veterans with Hannah Berner

    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 omnystudio.com/listener for privacy information.

  • Sep 13, 2021 · 48 min

    Mr. & Mrs. Unglert

    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 6, 2021 · 48 min

    F-Boys Will Be Boys

    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 information.

  • Aug 30, 2021 · 59 min

    Bad at Breaking Up

    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 https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Aug 23, 2021 · 57 min

    Baby Daddy

    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-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Aug 16, 2021 · 51 min

    Girl on Girl

    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 12, 2021 · 54 min

    We're on Island Time

    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-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jul 31, 2021 · 57 min

    The Return of Bennifer

    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 26, 2021 · 57 min

    A Nice Ring to It

    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 19, 2021 · 32 min

    Conjugal Visits

    Britney and Rachel from “Love After Lockdown” tell Dean and Jared how to find the man of your dreams… even if he’s in a jail cell. And, find out exactly how much it would cost for Jared and Ashley to make a sex tape! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jul 17, 2021 · 19 min

    Daddy Lessons

    There’s a new member of Bachelor Nation coming soon! Jared answers all the tough questions about his new role as a father, and he gets a few tips along the way! Find out everything about Jared and Ashley’s bundle of joy! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jul 12, 2021 · 53 min

    From Dating in Bars to Dating Behind Bars

    A long distance relationship is tough, but have ever wondered what it’s like to date someone in prison?? Dean and Jared talk to Elizabeth Greenwood, who spent years following love and marriages within America’s prison system. You’ll be surprised at what you might learn about your own relationship! And Jared reveals one of his more intimate “secrets” about something that happened on the golf course. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jul 5, 2021 · 53 min

    Going, Going Gonorrhea

    Dean and Jared talk to OB/GYN and health expert Dr. Jessica Shepherd to learn everything you want to know about STDs… but were afraid to ask! Nothing is off limits and both Dean and Jared reveal parts of their sexual history that will shock you! Does your dating profile need a refresh? Learn how strangers on social media might be the best help for making your profile irresistible. And would you help pay for your own engagement ring… if it meant a BIGGER diamond?? Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jun 29, 2021 · 1 hr 1 min

    Quarantine Slump

    Has your sex life taken a nose dive during the pandemic? You’re not alone. Dean and Jared share the hard truths about their sex drives and what you can do to spice things up! Can you be friends with your ex? Dean and Jared talk to the stars of TLC’s “You, Me and My Ex” and hear how they make their relationship work when an ex is very much still in the picture. And, we try to figure out exactly how Nick Cannon has so many kids!! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.