HELP! I Suck at Dating

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Latest Episodes:

Parental Control Feb 18, 2022

Show notes

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??

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Not Your Average Joe with Annaliese Puccini Feb 14, 2022

Show notes

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!

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Baby Marathon Feb 11, 2022

Show notes

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!

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Speed Dating with Dean & Caelynn Feb 07, 2022

Show notes

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!

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Baby Brady Feb 02, 2022

Show notes

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.

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Crushing Hard with Annaliese Puccini Jan 31, 2022

Show notes

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!

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Marriage Boomers Jan 27, 2022

Show notes

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”.

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It’s Complicated with Angela Amezcua Jan 24, 2022

Show notes

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”??

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Life on Other Planets with Kendall Long Jan 17, 2022

Show notes

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!

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Pickles are Cucumbers with Kelsey Weier Jan 10, 2022

Show notes

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!

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