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HELP! I Suck at Dating

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HELP! I Suck at Dating

  • 979 episodes
  • Updated Monday

Episodes979

  • Feb 8, 2021 · 43 min

    Mensches & Schmucks

    Dean spills on his wedding with Caelynn and if we’ll see them tie the knot on TV! We find out how Ashley’s parents reacted when they first met Jared Plus, hear some crucial advice on how to find a “mensch” in your city! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Feb 1, 2021 · 1 hr

    Open Ended Questions

    Dean opens up about being in an open relationship! Jared tries to figure out if Ashley is more obsessed with him than he is with her. And, we talk to psychologist and relationship expert Guy Winch about how to tell that a couple is going to break up after spending 90 seconds with them. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jan 25, 2021 · 54 min

    Just a Bling Thing

    Everyone is obsessed with Bling Empire and Kevin and Kim are here to tell all. Kevin Kreider and Kim Lee share the one big mistake most guys make early in dating. Dean finally reveals what happened in his relationship with Bri and if he would have chosen her in Paradise! And if that wasn’t awkward enough for Caelynn, we also hear about how their sex life has changed since Dean’s ski injury. Jared and Dean hold nothing back when sharing their true feelings on Dale and Clare’s break-up! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jan 18, 2021 · 1 hr 4 min

    The Toxic Avenger

    What are your toxic dating habits?? Do you know? Dean and Jared run down the most common toxic parts of relationships with Courtney Robertson from Ben Flajnik’s season and Jake Ellis, Jared’s buddy from Bachelor in Paradise Australia! Find out how Dean was involved with conceiving Courtney’s baby! And Jared opens up about one of HIS most toxic dating traits. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jan 11, 2021 · 1 hr 1 min

    From Gas Tanks to Wedding Bells

    Dean and Jared hang out with Marquel Martin (Andi Dorfman’s season and season 1 of Paradise) who was actually in the running to be the first black Bachelor. We hear his honest reaction to Matt James and we find out why he didn’t become the lead years ago. Plus, he shares everything about his recent engagement and has some tips on how you can meet your special someone without apps or the internet! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Jan 4, 2021 · 57 min

    Aloha Annaliese!

    What would you do if you made plans to move away to a remote island with your significant other… and they dumped you weeks before you leave?? That’s what happened to Annaliese from Arie’s season and she tells Dean and Jared all about it! You won’t believe the drama she’s been through in the last few months, but she’s ready to share the lessons she’s learned along the way. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 31, 2020 · 44 min

    New Years Eve Q&A Live on Stereo!

    Before we say a final goodbye to 2020, Dean and Jared are baring all with a Q&A like you’ve never heard before! Find out the issue that might cause major problems for Dean and Caelynn in the future! And Jared shares the crazy story about how he got arrested! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 29, 2020 · 59 min

    Castles & Cameras

    Jared reveals the intimate gift he got Ashley for Christmas that might jumpstart their road to pregnancy. Dean shares why romance movies are horrible role models for a relationship. And we talk to Garrett Marcantel, the gay lead on "12 Dates of Christmas", about his experience finding love in front of a camera. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 21, 2020 · 55 min

    Love Across the Pond

    Katie Morton is back with Dean and Jared and she has a MAJOR life update! Plus, Chief Dating Officer Maya Ezratti helps Dean realize a major insecurity in his relationship with Caelynn. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 14, 2020 · 51 min

    I Like You Maximumly with AJ McLean

    Dean and Jared hang with AJ McLean from The Backstreet Boys and his Pretty Messed Up podcast cohosts Rene Elizondo and Cheryl Burke from Dancing with the Stars! AJ has an INSANE catfish story that easily beats anything on the MTV show. Plus, find out how to get married twice without ever proposing! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 11, 2020 · 44 min

    Dean and Jared's Q&A Live on Stereo!

    Dean and Jared are going uncensored & unfiltered to answer your dating and relationship questions live on the Stereo App. Find out who has already picked out baby names! And hear some amazing marriage advice from Jared and an incredibly intimate detail about Dean! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Dec 7, 2020 · 48 min

    Lost in the DMs

    If a bikini model DM’d your boyfriend or husband… what would he say?? Dean and Jared talk to model Paige Woolen who has turned sliding in to the DM’s as a genius way to catch cheating partners. Sydney Lotuoaco is our guest cohost! She explains why after months of quarantine, she’s pretty much married! And Dean has a totally unexpected announcement about his life with Caelynn! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 30, 2020 · 1 hr 3 min

    Socially Distant Social Life

    Angela Amezcua from Bachelor in Paradise and Nick Viall’s season of The Bachelor helps Dean and Jared understand the weird rules of pandemic dating! Sleeping with someone on the first date is now “do I get within 6 feet of someone on the first date??” We get the lowdown on her close friend (and newly pregnant) Krystal Nielsen! And we hear the REAL story of why she went full “runway model” at Chris and Krystal’s wedding! Plus, Angela shares her #1 worst dating experience and you won’t believe what happened! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 23, 2020 · 1 hr

    Let's Get Bibi

    Bibiana Julian from Arie’s season spills everything about her new relationship and opens up about how quarantine has totally changed how she dates. If you’re struggling with dating right now, you have to hear her ONE rule when it comes to social media! Jared tells us about making a cameo with Ashley on The Bachelorette! They were on location when the Tayshia rumors started… what did they find out?? And we take a trip to Love Island and get to know winners Caleb and Justina! Are they “together”??? Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 19, 2020 · 53 min

    What a Girl Wants: Bibiana Julian

    Bibiana Julian from Arie’s season is here to tell us What a Girl Wants! She opens up about her dating life and how when she changed her mindset it changed her life. It can happen for you too! And find out what to do if you’re in a “situationship”! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 16, 2020 · 50 min

    Caelynn in the Hot Seat

    Dean and Caelynn are coming out of the van – and out of their shell! Caelynn is Dean’s cohost for a Q&A where NOTHING is off limits. Something in Caelynn’s past made Dean have second thoughts… find out what happened! Does Caelynn still have feelings for Connor after their time in Paradise? And Dean has cheated multiple times in the past… is it true that “once a cheater always a cheater”? Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 9, 2020 · 48 min

    The Man Whisperer

    Jared has a new cohost this week that knows him better than ANYONE… his wife Ashley! Relationship expert Lauren Frances helps Jared & Ashley uncover something that went totally wrong on their first date. And she has some amazing tips to help you improve your dating profile during the pandemic. Plus, Jared reveals the thing about Ashley that annoys him the most. You won’t believe her reaction! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Nov 2, 2020 · 1 hr 5 min

    Caelynn Bares All

    You wanted it... and now you’ve got it! Dean’s girlfriend Caelynn Miller-Keyes is here for a full interview and NOTHING is off limits! Find out what she honestly thought of dean when they were on paradise! She has something shocking to admit about the first few months of their relationship. How has Dean changed?? Whats the REAL story about their wedding bands? Will they have kids??? What was their worst date?? Who said I love you first??? All is revealed! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Oct 29, 2020 · 58 min

    What a Girl Wants: Elyse Dehlbom

    Elyse from Colton’s season tells us What a Girl Wants! We find out what the self proclaimed “Bachelor Cougar” is looking for in a relationship! And we finally get the REAL story on her quarantine hook-up! Find out which member of Bachelor Nation has been spending some “quality time” with Elyse! And we call in relationship expert Dr. Kirk for some crucial dating advice and his honest take on Clare’s season of The Bachelorette! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Oct 26, 2020 · 55 min

    Caelynn Joins the Suck Army!

    Caelynn joins Dean and Jared for the first ever interview together! She admits the one thing about Dean that may be the end of their relationship! Dean and Jared catch up with Elyse from Colton’s season and she spills everything about a quarantine hook up with a popular member of Bachelor Nation. You won’t believe what happened when she was up to be The Bachelorette! And on National “Call Your Mother in Law Day”, Jared calls Ashley’s mom and she gets a little too honest about her first impression of Jared. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.