HELP! I Suck at Dating

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Latest Episodes:

Help! We Suck at Being Newlyweds Feb 14, 2023

Show notes

Dean and Jared are joined with Dean’s future wife Caelynn Miller-Keyes as a permanent co-host.

Together learning the ins and outs of marriage, and there’s no telling what other life lessons they’ll pick up along the way!

We get a look at Dean’s STRICT wedding guest list and we find out if and WHEN they might have kids!

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Big Tipper Energy with Courtney Robertson Feb 06, 2023

Show notes

Courtney Robertson from Ben Flajnik’s season of The Bachelor connects with Jared over something EVERYONE should know before going out on a date: How to be a good tipper!
Courtney opens up about what it was like to be seen as a “villain” on The Bachelor, and she has some advice for women who want to “shoot their shot” – The DM slide worked for Courtney!
And… Jared has a sneak peek at the NEW version of Help I Suck at Dating, coming soon!

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Hard vs Soft Launch with Jill Chin Jan 30, 2023

Show notes

Jill Chin from Clayton's season and BIP is hanging out with Dean and Jared and ready to drop a hard launch... or maybe a soft launch? We try to figure out what exactly it is.

What is "Bachelor Head" and who in the franchise is guilty of it?? Dean and Jared spill about how appearing on the show can change a personality.

And we get into the weeds on Miley Cyrus' new song "Flowers" with an inside source close to Bachelor Nation!

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Opposite Icks with Hunter Haag Jan 23, 2023

Show notes

Hunter Haag from Clayton’s season and Bachelor in Paradise is getting caught up with Dean and Jared, and telling us everything about dating from the perspective of a REAL Disney princess!
She gets real about her time on Paradise and how it feels to be most famously known for…. IBS.

We run down the most common “icks” people have in relationships, and Dean confronts Jared about why he missed Dean and Caelynn’s engagement party! Things get HEATED!

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Sharing Dating Wisdom with Kiarra Norman Jan 19, 2023

Show notes

Kiarra Norman from Peter Weber's season is back with Dean to help members of #SuckArmy get through some serious dating problems!

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Turn the Drama On with Kiarra Norman Jan 16, 2023

Show notes

Kiarra Norman from Peter Weber’s season is hanging out with Dean and sharing why she thinks she could be next to join the Engaged Club!
Dean and Kiarra get real about how people change when the cameras are on and what it was REALLY like to film The Bachelor.
Plus, they revisit their old Bachelor questionnaires from the casting process and you won’t believe some of their answers!

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Dating Tipline with Lauren Jones Jan 12, 2023

Show notes

Dean and Jared are teaming up with Lauren Jones from Peter Weber's season to help members of #SuckArmy suck less at dating!

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March of the Penguin with Lauren Jones Jan 09, 2023

Show notes

Lauren Jones from Peter Weber's season is hanging out with Dean and Jared and sharing EVERYTHING about her dating life.

Did she miss out by skipping Paradise?? Jared and Dean share the honest truth.

Plus, find out why Jared thinks Ashley "settled" with him.

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First Date of 2023 Jan 03, 2023

Show notes

Happy New Year! Dean and Jared reflect on their holidays, the life lessons they learned in 2022, and Dean shares the trials and tribulations of wedding planning.

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Superfriends with Jenna Cooper Dec 22, 2022

Show notes

Jenna Cooper from Arie’s season is throwing a holiday party with Dean and Jared!
She shares all about her painful experience with Jordan after their time on Paradise and we finally clear up what REALLY happened.
Plus, Jenna helps dish out some much needed relationship advice to members of #SuckArmy!

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