HELP! I Suck at Dating

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Latest Episodes:

Long in the Front, Short in the Back Jun 13, 2022

Show notes

When you come off The Bachelor, it’s not always a fairy tale romance! Dean and Jared discuss the difficult first year that many Bachelor couples face after the show.

Should Dean expect something from Caelynn if he gets her an engagement ring??

Plus, Jared reveals a big change coming in his relationship with Ashley.

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Shrinkage with The Shrink Chicks Jun 09, 2022

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Anna Redman from Matt James’ season is back with Dean and Jared for a therapy session with the Shrink Chicks! Emmalee and Jen are best friends that became marriage and sex therapists and now want to pull back the stigma on therapy.
Hear some amazing advice on how to bring up therapy with your partner, when is the best time to seek therapy, and how to get mental health help on a budget!
And, Dean opens up about his experience with therapy and why it’s important to be honest with your therapist.

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Kicked Out of the Restaurant with Anna Redman Jun 06, 2022

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Jared and Dean catch up with Anna Redman from Matt James’ season! She spills everything about her relationship with Chris Bukowski and we find out when they plan on taking “the next step”!
Plus, Anna shares some brutally honest advice for anyone going to Paradise!

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Double the Fun with Daniella McBride May 30, 2022

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Jared and Dean are hanging out with one of the newest parents from Bachelor Nation: Daniella McBride from Sean Lowe’s season! She had twin boys last year and has some advice for Jared on how to get to the “fun” baby stage.
We hear the status of Daniella’s 7 year relationship and why they haven’t gotten married!
Plus, who should change their name when getting married??

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Roses for Housewives with Leah McSweeney May 26, 2022

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Pieper James is back with Dean and Jared to hang with Leah McSweeney from The Real Housewives of New York! Leah is a HARDCORE Bachelor fan… but would she ever go on the show??

She has an important lesson to share that she picked up while following Jared and Ashley’s love story.

And, find out the ONLY reason (according to Leah) that you should stay in touch with an ex!

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Popping the Question with Pieper James May 23, 2022

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Dean and Jared get to know fellow Paradise alum Pieper James! We hear the real story of her controversial romance with Brendan and we find out the truth behind rumors of their break-up.

Hear the good and the bad that comes with a long distance relationship and we get the latest on what's going on between Pieper and Natasha Parker!

Plus, Dean reveals a BIG decision that could completely change his future with Caelynn

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Mating Season with Austin Nogiec and Paige Dacanay from “Love in the Jungle” May 19, 2022

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Dean is back with Sarah Herron and if you thought finding love on The Bachelor was strange, wait until you meet Austin and Paige from “Love in the Jungle” on Discovery+!
We hear all about trying to make a romantic connection by embodying an animal and reenacting mating rituals. Does it work??
What animal would Sarah take on if she was sent to jungle? All is revealed!

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Rocky Mountain High with Sarah Herron May 16, 2022

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Dean is going one on one with Bachelor in Paradise OG Sarah Herron (Sean Lowe’s season) for a very special episode! Sarah and Dean have an unexpected connection that goes much deeper than you might think!

Sarah opens up about her journey with IVF and she and Dean reveal why Paradise can sometimes feel like Hell.

Plus, find out why Dean and Caelynn are in a “rut”!

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The Return of Love Man May 12, 2022

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Dean and Jared are back with Katie Morton! We talk to Lisa Bilyeu, cofounder of Quest Nutrition (yes THOSE health bars!) and she shares some incredible advice on how to overcome hardship and achieve success.

If you've ever struggled with confidence, you need to hear this conversation.

And when we needed him most, Love Man returns!

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Kicking it with Katie Morton May 09, 2022

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Katie Morton from Colton’s season is back with Dean and Jared, and she might STILL suck at dating.
She’s in a long term and VERY long distance relationship, and she’s ready to give us the real story on dating someone overseas! Find out if she’s going to spend a lot of time in an immigration office OR if we’ll see her back on the beach in Paradise!

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