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HELP! I Suck at Dating

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HELP! I Suck at Dating

  • 979 episodes
  • Updated Monday

Episodes979

  • May 12, 2022 · 18 min

    The Return of Love Man

    Dean and Jared are back with Katie Morton! We talk to Lisa Bilyeu, cofounder of Quest Nutrition (yes THOSE health bars!) and she shares some incredible advice on how to overcome hardship and achieve success. If you've ever struggled with confidence, you need to hear this conversation. And when we needed him most, Love Man returns! See omnystudio.com/listener for privacy information.

  • May 9, 2022 · 36 min

    Kicking it with Katie Morton

    Katie Morton from Colton’s season is back with Dean and Jared, and she might STILL suck at dating. She’s in a long term and VERY long distance relationship, and she’s ready to give us the real story on dating someone overseas! Find out if she’s going to spend a lot of time in an immigration office OR if we’ll see her back on the beach in Paradise! See omnystudio.com/listener for privacy information.

  • May 5, 2022 · 41 min

    Bi-Coastal Dating with Tammy Kay Ly

    Jared connects with Tammy Kay Ly from Peter Weber’s season and Bachelor in Paradise to try and figure out dating when you travel between 3 different cities! Tammy has been all over, so she has firsthand knowledge on dating in LA, NY, and Mimai, all while working 6 jobs! And how do guys react when a woman approaches THEM? Should women be more proactive in shooting their shot? See omnystudio.com/listener for privacy information.

  • May 2, 2022 · 44 min

    Significant Other Time at the Help I Suck at Dating/Almost Famous Crossover Party!

    Dean and Jared are hanging out with Ben Higgins and Ashley I from the Almost Famous podcast for a special crossover party presented by Pandora Jewelry! We're putting the spouses in the hot seat! Ashley and Caelynn join in to answer the most intimate questions about Jared and Dean. But Ben isn't safe! We bring in his new wife Jess to get the real story on what it's like to be married to "Perfect Ben"! See omnystudio.com/listener for privacy information.

  • Apr 25, 2022 · 47 min

    Showered with Love

    Dean is live from a Wyoming mountaintop to try and figure out how to suck less at dating! Dean opens up about how Caelynn has changed his life and anyone who can smell him is VERY grateful. But it goes both ways, and we find out which of Dean's dirty habits have rubbed off on Caelynn. And Jared is concerned about baby Dawson's exposure to social media. How do you limit access as parents without being overprotective?? See omnystudio.com/listener for privacy information.

  • Apr 21, 2022 · 24 min

    How to Make a Match

    Kendall Long and Deandra Kanu return with Dean to get to the bottom of what people are REALLY looking for in a partner. We talk to the Matchmaking Duo about the secret details that will help you land the person of your dreams! They have 2 IMPORTANT tips that are guaranteed to land you more dates with higher quality people, and we find out the perfect mindset to have when starting to date someone new. See omnystudio.com/listener for privacy information.

  • Apr 18, 2022 · 43 min

    A Hard Launch with Kendall Long and Deandra Kanu

    Kendall Long is back with Dean and and she has some BIG news to share about her "hard launch" on Instagram. And we talk to Deandra Kanu from Peter's season about the challenges of dating in LA. Do apps still work?? See omnystudio.com/listener for privacy information.

  • Apr 14, 2022 · 20 min

    It’s Now or Never with Randall and Jake from The Ultimatum

    If you can’t get enough of “The Ultimatum” on Netflix, you don’t want to miss this episode! Dean and Jared are back with Serena Pitt from Matt James’ season and this time we have Randall and Jake from “The Ultimatum”! Find out what caught Randall off guard about going on the show, and Jake reveals what changed his mind when he refused to go on. And, we learn what “The Ultimatum” can teach us about relationships and healthy growth. See omnystudio.com/listener for privacy information.

  • Apr 11, 2022 · 43 min

    Cleanup on Aisle 5 with Serena Pitt

    Serena Pitt from Matt James’ season and Bachelor in Paradise joins Dean and Jared to catch up on her romance with Grocery Store Joe! She spills everything about how their relationship has changed since moving to New York together and we find out why they might be getting married sooner than you think! Plus, Serena tells us the REAL story of why she sent herself home on Matt’s season. See omnystudio.com/listener for privacy information.

  • Apr 7, 2022 · 24 min

    Resting Betch Face with Jordana Abraham

    Genevieve Parisi from Clayton’s season is back with Jared to try and figure out dating in 2022 with Jordana Abraham, founder of Betches! Genevieve WISHES she was married and Jordana has some advice on how to find “the one”! Do you think technology has helped or hurt dating?? We try to understand how dating has changed and where its headed in the future. Plus, Jordana is a HUGE Bachelor fan and has some thoughts on the state of the franchise. See omnystudio.com/listener for privacy information.

  • Apr 4, 2022 · 37 min

    Make Relationships Flirty Again with Genevieve Parisi

    Genevieve Parisi from Clayton’s season is hanging out with Jared this week and spilling EVERYTHING about her time getting to know the “real” Clayton. Is it possible to see her on the beach in Paradise?? Jared gets Genevieve to open up about her future with the franchise. Plus, we share tips on how to make your long term relationship “flirty” again! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Mar 28, 2022 · 1 hr 4 min

    Naked and Afraid

    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.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Mar 24, 2022 · 28 min

    A Decent Proposal

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

  • Mar 21, 2022 · 37 min

    Emoji Interpreter with Sierra Jackson

    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/listener for privacy information.

  • Mar 17, 2022 · 23 min

    Millionaire Match-Up

    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 finger. Plus, Steven tells us if his bromance with Kurt from Joe Millionaire was able to survive the competition of the show! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Mar 14, 2022 · 45 min

    Return to Paradise with Abigail Heringer

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

  • Mar 10, 2022 · 20 min

    Check the Receipts with Lauren Speed-Hamilton

    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 Jared reveals the harsh truth about the "work" that comes with trying for a baby. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Mar 7, 2022 · 39 min

    Breaking Up is Hard to Do with Heather Martin

    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.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Mar 3, 2022 · 34 min

    Jared and his “Things”

    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. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.

  • Feb 28, 2022 · 39 min

    The Kids Are Alright with Caroline Lunny

    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 omnystudio.com/listener for privacy information.