HELP! I Suck at Dating

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Latest Episodes:

Sucky Daters Tipline! Nov 10, 2022

Show notes

Jared is solo working the phones at the Sucky Daters Tipline to help members of #SuckArmy with their dating problems!

See omnystudio.com/listener for privacy information.

It Has a Nice Ring to It with Caelynn Miller-Keyes Nov 07, 2022

Show notes

Now that we’ve heard the story of Dean’s proposal after a treacherous hike, it’s time for Caelynn’s side of the story.
Did she expect a proposal after the lost ring?? What are their plans for marriage and starting a family?? Will Caelynn still propose to Dean??
All these questions and more will be answered in this unfiltered Help I Suck at Dating!

See omnystudio.com/listener for privacy information.

Sucky Daters Helpline with Olivia Caridi Nov 03, 2022

Show notes

Olivia Caridi from Ben Higgins' season teams up with Jared to help #SuckArmy with their dating troubles!

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Go On 2 Dates and Call Me in the Morning with Olivia Caridi Nov 01, 2022

Show notes

While Dean basks in post-engagement bliss, Jared catches up with Olivia Caridi from Ben Higgins’ season!

Olivia shares her routine of going on at least 2 dates a week to try and get herself out there.

She gets real about what its like to date in New York City and how it’s possible to have too much of a good thing.
Plus, we find out if she’ll ever return to the Bachelor franchise!

See omnystudio.com/listener for privacy information.

Dean on One Knee Oct 31, 2022

Show notes

It finally happened! Dean is back from his exotic proposal to Caelynn and he’s ready to share all the magic, all the tears, and every intimate detail of how he popped the question!

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Sucky Daters Anonymous with Leah Block Oct 27, 2022

Show notes

Leah Block from Ben Higgins’ season is back with Dean and Jared to help members of #SuckArmy with their dating problems!

See omnystudio.com/listener for privacy information.

Lord of the Rings with Leah Block Oct 24, 2022

Show notes

Dean is getting ready to pop a BIG question.. if he can find the ring! Dean and Jared are hanging out with Leah Block from Ben Higgins' season and we're hearing all about Dean's proposal plans (or lack thereof).

Plus, Leah shares why she knows her own engagement might be coming soon, and how you can spot similar signs in your relationship!

See omnystudio.com/listener for privacy information.

Dating Questions and Sucky Answers! Oct 22, 2022

Show notes

Dean and Jared are sharing their (somewhat) expertise in the world of dating to help members of #SuckArmy with their relationship issues!

See omnystudio.com/listener for privacy information.

Pull the Parachute with Magi Tareke Oct 17, 2022

Show notes

Magi Tareke from Matt James' season is here to help Dean and Jared find the secrets to sucking less at dating.

We try to figure out the success rate of arranged marriages, why Instagram is the best dating app, and Dean shares some skydiving tips because sometimes dating feels like a free fall.

See omnystudio.com/listener for privacy information.

Sucky Dater Hotline with Tahzjuan Hawkins Oct 13, 2022

Show notes

Tahzjuan Hawkins from Colton’s season is back with Dean and Jared to help #SuckArmy with their dating woes!

See omnystudio.com/listener for privacy information.