HELP! I Suck at Dating

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979 episodes
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Episodes979

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Feb 24, 2022 · 31 min
Mind Your P’s and Q’s
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 thinks he and Caelynn are “total opposites”! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 21, 2022 · 32 min
Dance Down the Aisle
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.com/listener for privacy information.
Feb 18, 2022 · 27 min
Parental Control
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 ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 14, 2022 · 32 min
Not Your Average Joe with Annaliese Puccini
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 for privacy information.
Feb 11, 2022 · 25 min
Baby Marathon
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 https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 7, 2022 · 34 min
Speed Dating with Dean & Caelynn
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 2, 2022 · 20 min
Baby Brady
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.
Jan 31, 2022 · 41 min
Crushing Hard with Annaliese Puccini
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 27, 2022 · 27 min
Marriage Boomers
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 24, 2022 · 45 min
It’s Complicated with Angela Amezcua
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 17, 2022 · 1 hr
Life on Other Planets with Kendall Long
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 10, 2022 · 50 min
Pickles are Cucumbers with Kelsey Weier
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 privacy information.
Jan 3, 2022 · 58 min
New Year’s Resolutions with Kelley Flanagan
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://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Dec 20, 2021 · 51 min
Tis the (Cuffing) Season
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/listener for privacy information.
Dec 13, 2021 · 59 min
We Were on a Break!
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 6, 2021 · 45 min
F-Boy Dean
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.
Nov 29, 2021 · 58 min
Ghosts of Bachelor Couples Past
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 22, 2021 · 49 min
Caelynn Pops the Question
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 privacy information.
Nov 15, 2021 · 42 min
A Family Affair
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.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Nov 8, 2021 · 1 hr 4 min
Cat People & Dog People
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 for privacy information.