HELP! I Suck at Dating

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Latest Episodes:

A Decent Proposal Mar 24, 2022

Show notes

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!

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Emoji Interpreter with Sierra Jackson Mar 21, 2022

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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!

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Millionaire Match-Up Mar 17, 2022

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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!

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Return to Paradise with Abigail Heringer Mar 14, 2022

Show notes

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!!

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Check the Receipts with Lauren Speed-Hamilton Mar 10, 2022

Show notes

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.

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Breaking Up is Hard to Do with Heather Martin Mar 07, 2022

Show notes

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!

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Jared and his “Things” Mar 03, 2022

Show notes

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.

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The Kids Are Alright with Caroline Lunny Feb 28, 2022

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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!

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Mind Your P’s and Q’s Feb 24, 2022

Show notes

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”!

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Dance Down the Aisle Feb 21, 2022

Show notes

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.

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