HELP! I Suck at Dating

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Latest Episodes:

Must Love Dogs Jun 24, 2020

Show notes

In the wake of Dean’s major hair change, we discuss what hairstyle women like best on a guy.

Then Pappy and Lois' dad's discuss DOGS and DATING!

How much can you tell about a person how they treat their dog? Dean and Jared learn that a new relationship might only be a leash length away!

They talk to Leigh Isaacson, founder of the Dig app, about launching a dating app based around hooking up “dog people”.

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Never Have I Ever Jun 15, 2020

Show notes

It’s Caelynn’s birthday week… what’s Dean gonna do?? He shares his plans (or lack thereof!)

We play a game of Never Have I Ever and you won’t believe what Dean reveals!

Plus Dean and Jared talk to Leah Van Dale and her boyfriend Matt Polinsky (known in the WWE as Carmella and Corey Graves) about what it’s like being in a relationship as pro wrestlers.

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Wear Protection Jun 08, 2020

Show notes

Dean and Jared catch up with Tayshia Adams and she shares her thoughts on the state of the country right now. She shares her experience growing up with biracial parents and we hear about how dating is going for her… even in quarantine.

Plus Dean and Jared talk about the new rules for safe sex: wearing masks!

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Working Towards Change Jun 04, 2020

Show notes

Dean and Jared have an honest and vulnerable conversation about racism and the protests against police brutality throughout the nation.

Jubilee Sharpe (The Bachelor - Ben Higgin’s season and Bachelor in Paradise) joins Dean and Jared to educate, enlighten, encourage them about matters of race. They also address the underrepresentation of Black people on The Bachelor.

Dr. Ish discusses racial issues and how they affect our relationships. He shares resources that people can use to better understand the experiences of Black people in America.

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Spin the Bottle May 27, 2020

Show notes

Dean and Jared open up about their intimacy struggles during quarantine, especially for Jared, who’s been on lockdown with his in-laws for months.

They share an incredibly honest conversation about self-esteem issues and how they can affect intimacy.

But then they spill all during a SPICY round of “Spin the Bottle”!

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7 Minutes in Heaven May 20, 2020

Show notes

Dean and Jared discuss Mary-Kate Olsen’s split from Pierre Sarkozy and her “iron clad prenup” which opens a TON of questions. What’s the oldest you could date?? Would you ever get a prenup? Are they a smart idea??

And we play a round of “7 minutes in Heaven”, where the boys get to talk about anything they want! You won’t believe what Dean reveals about his new love: the saxophone.

Plus Jared talks to one of his favorite authors Ben Mezrich!

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Wild Animals May 13, 2020

Show notes

Dean and Jared get open up about their “intimate moments” in a way we’ve never heard before! Plus we hear how dating in the public eye has changed the way they view relationships.

Dean and Jared talk to Sukanya Krishnan, host of “Find Love Live” on TLC. She tells about the challenges and advantages of playing matchmaker over video chat!

Plus, should you wait until after quarantine to define your relationship??

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Big Plans with Big Ed May 06, 2020

Show notes

When are Jared and Ashley going to have kids....we get an update. And, Dean & Caelynn may have already added to their family!

Plus, Dean and Caelynn open up about their future together, since their anniversary is coming up!

Dean & Jared talk to the breakout superstar of 90 Day Fiance… Big Ed! We get all the inside info on his relationship with Rose, including what caused their biggest fight!

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Getting Down in Lockdown Apr 29, 2020

Show notes

Even though everyone is in quarantine, there’s still a lot of hooking up happening, so Dean and Jared call in sex therapist and Bachelor alum Taylor Nolan. She helps us figure out why sex is often linked to shame and ways to have safe healthy sex while in quarantine.

and from the Netflix phenomenon “Too Hot to Handle”, Francesca Farago Zooms in with Dean and Jared. She spills everything about her future with Harry and we find out how she’s keeping things spicy while in isolation.

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What's APPropriate Apr 21, 2020

Show notes

Significant Other Takeover...Ashley and Caelynn steal the mics to reveal some intimate secrets about Dean and Jared!

Dating in the time of quarantine poses some strange challenges, and Dean and Jared are ready to get to the bottom of it all.

How to navigate the dating apps while in isolation. What stands out about profiles? How do you deal with catfish? All the answers and all the Help!

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