HELP! I Suck at Dating

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Latest Episodes:

Mother’s Day No More May 22, 2023

Show notes

Jared has a controversial take: should Mother’s Day be CANCELLED?? He explains why he thinks we don’t need the holiday anymore.
Caelynn reveals who does the heavy lifting in the intimacy department in her relationship with Dean, but it sounds like things are going well!

Plus, we get a wedding update, and surprising no one, Dean is missing a MAJOR detail.

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Courthouse I Do’s May 15, 2023

Show notes

After all this build up, Dean and Caelynn almost got married LAST WEEK! Jared shares his take on a “courthouse wedding” and why Dean and Caelynn need to do it!
Caelynn opens up about her fears and anxieties about her wedding dress, and we get a full recap of her dream bridal shower in Vegas!
Plus, Jared lets us in on life as a single dad while Ashley is out of town… and he might toally lose it before she gets back.

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Nip(ple) it in the Bud May 12, 2023

Show notes

The newlyweds are answering your emails and they go to some strange places!

We get into body hair removal and learn a little too much about Jared and Dean.
And things get TENSE when sharing how their significant others "hold them back"!

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Cloudy with a Chance of Bridal Showers May 08, 2023

Show notes

The Newlyweds are stressing this week! Caelynn is getting ready for her bridal shower but some major people will be missing... and one of them happens to be Dean!

Jared is dealing with single dad life after Ashley makes a last minute trip to Australia.

And, find out why Dean and Caelynn might be parents sooner than you thought!

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Hot, Not, or Botox May 01, 2023

Show notes

Do you think it’s hot when someone has a raspy voice?? You might be surprised at what Dean, Caelynn and Jared find hot in the opposite sex! We get into (too much) detail about what gets them going.

Plus, could Dean and Caelynn be moving AGAIN?? Find out where they might be relocating to, and Jared reveals some of the challenges he faced moving from LA back to Rhode Island!

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Brother to Mother Apr 24, 2023

Show notes

Caelynn and Dean are in the depths of wedding planning, and Caelynn has a shocking admission to make which brought her to tears. You won’t believe what’s on her mind!
And, we set the record straight about Dean and Caelynn’s plans for a “genetically similar” sperm donor.

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High Fives over Low T Apr 17, 2023

Show notes

Dean and Caelynn share the results of their fertility tests, which could mean that a Bachelor baby is in the future! But... wait until you hear why Dean might NOT be the father!

Plus, we get into all the details about our recent guest Lindsay Hubbard from Summer House and her "accidental hard launch" of Tayshia's possible new guy!

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The Newlyweds Bare All Apr 13, 2023

Show notes

Dean and Caelynn face off in the ultimate challenge: Who knows the other best??
Nothing is off the table as Dean and Caelynn answer intimate questions about each other, and it seems like Jared might know Dean better than his other half!
Plus, you won’t believe WHY Dean strips down in the middle of the podcast!

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Turning Summer House into a Summer Home with Lindsay Hubbard Apr 10, 2023

Show notes

Lindsay Hubbard from Summer House joins the Newlyweds to share the journey of saying yes to the dress! She’s getting close to the big day and things are getting heated!
Find out if her wedding will be televised, and why she almost spent her engagement in the emergency room!
Plus, Lindsay shares the story of why she decided to freeze her eggs.

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You May Prank the Bride with Ling and Lamb Apr 03, 2023

Show notes

Dean, Jared and Caelynn discuss why they have no hope for Bachelor couples these days. Ouch!Caelynn reveals how she really felt when Dean stood her up the first time they had planned to hang out. Double Ouch!!

And, every strong relationship is built on trust, communication, and the ability to pull a good prank! Dean, Caelynn and Jared talk to Tik Tok stars Ling & Lamb about what it’s like to put their ENTIRE relationship on social media, and how their love can withstand some of the most intense pranks they pull on each other.

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