HELP! I Suck at Dating

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Latest Episodes:

New Year’s Resolutions with Kelley Flanagan Jan 03, 2022

Show notes

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??

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Tis the (Cuffing) Season Dec 20, 2021

Show notes

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!

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We Were on a Break! Dec 13, 2021

Show notes

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!

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F-Boy Dean Dec 06, 2021

Show notes

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.

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Ghosts of Bachelor Couples Past Nov 29, 2021

Show notes

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!

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Caelynn Pops the Question Nov 22, 2021

Show notes

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!

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A Family Affair Nov 15, 2021

Show notes

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??

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Cat People & Dog People Nov 08, 2021

Show notes

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!

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Bae Watch Nov 01, 2021

Show notes

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??

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See omnystudio.com/listener for privacy information.

Don't Forget to Swipe Oct 25, 2021

Show notes

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.

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