HELP! I Suck at Dating

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Latest Episodes:

Dean There, Done That Apr 15, 2019

Show notes

Dean tells us he’s been feeling a lot healthier and confident lately, but to really evaluate what that means, we talk to “Possibilitarian” Cherie Healey. She helps Dean face some of his unprocessed grief from losing his mother, and she shares some incredible advice on how to deal with fear. Plus, Dean lets us in on a HUGE project he’s been working on, and we hear about how his Coachella trip has left him thinking about a recent ex girlfriend.

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Pet Names with GiGi Gorgeous Apr 08, 2019

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The rumors are circulating that Dean is going back to Paradise, and he finally sets the record straight for you. He hints at a truly epic entrance, and tells us that this new season could completely change the way everybody looks at him.

We talk to model GiGi Gorgeous about her journey. She tells us her theory on why transgendered dating is better than cisgendered dating.

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Dating with Dignity Apr 02, 2019

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Dating coach Marni Battista joins us to share some advice on how to meet people that have "evolved" to a more serious level in relationships.

And we tackle some dating issues from 3 different perspectives: a single person, someone in a committed relationship, and one in a new relationship.

Also, we figure out the male equivalent to flowers... what's a quick gift you can get for your guy to show that you care and are thinking of him?

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Non Negotiables with Reza Farahan Mar 26, 2019

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It's a girls day on the podcast when Vanessa hangs out with her friend Mikaela Whightman from Bachelor Canada. Together, they tackle the question "can you ever be satisfied in love?"

Reza Farahan from Shahs of Sunset stops by, and reveals why hands and teeth could be a clue to what kind of kisser you are.

Plus, Vanessa opens up about her anxiety, and how she deals with panic attacks.

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Single Parents with Kimrie Lewis Mar 19, 2019

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Kimrie Lewis from Single Parents on ABC is hanging out with Dean, Jared & Vanessa, and all their worlds collide when they talk about the Single Parents/Bachelor crossover episode. Kimrie tells us about how her ex was the DJ at her wedding, but at the moment, Kimrie is painfully single, so we see if Dean or Jared can set her up with one of their Bachelor buddies.

Plus, we figure out why women feel heartbreak worse than men, and we get an inside update on Bachelor in Paradise from Dean, who spent some time with some of the guys recently.

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I Used to Be a Cougar with The Bubbies Mar 12, 2019

Show notes

Dean’s back from another trip around the world! Blake Hortsmann stops by the studio. Blake reveals if Bachelor Nation pals Jason Tartick and his new girlfriend Kaitlyn Bristowe have tried to hook him up with anybody. We find out what’s been on his mind while watching Colton.

Dean and Colton both had a shot at being the Bachelor and they open up about that!

And the story of Caelynn sliding into Dean’s DMs has been everywhere, so Dean has to set the record straight, and tell us all the dirty details of what went down in those messages.

Then we welcome The Bubbies into the studio, and who better than Grandmas to help us STOP SUCKING AT DATING! They have some crucial words for Vanessa, who recently hit a huge milestone in her new relationship, and you don’t want to miss their answers to your dating questions!

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Baecations with Dax Holt Mar 04, 2019

Show notes

HOW DO YOU BUTTER YOUR BREAD? Etiquette specialist Amy Rainer helps us understand the proper way to do it. You might recognize Amy from Colton’s bread buttering on last week’s episode of The Bachelor. Did you know there’s a right and wrong way to pass the salt? She has some little known rules that may save your next date!

We play a round of “10 Questions with Vanessa Grimaldi”!

And Dax Holt from TMZ and Access Live stops in to share some of his celebrity expertise, and the dos and don’ts for couples that want to share their relationship on Instagram. He warns us of the effects a vacation (even a short one) can have on a relationship, then Jared and Vanessa open up about some of the crazier dates they went on during The Bachelor.

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Alter Egos Feb 25, 2019

Show notes

Vanessa fills us in on her first Valentine’s Day with her new guy, and we hear about her clapback against a body shaming troll.

Plus, we talk to author Sabrina Must about her new book “A Terrible Dater”. With a title like that, she’ll fit right in on this podcast!

And life coach Mike Bauer introduces Vanessa and Jared to their alter egos... Barfola and Captain Suckbag!

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Your Chairlift or Mine? Feb 18, 2019

Show notes

These days, it seems like dating apps are the best way to meet people, but our expert says that might not be true! Dean and Vanessa talk to Melissa Brown, CEO of “Its Just Lunch”, about the advantages of getting to know people in person instead of just chatting on apps. And if you think you’ve tried every dating gimmick, strap your skis on, and see what happens during “Chairlift Speed Dating”.

Then, Brittany Rose from Temptation Island stops by to talk about her experience on the show, and her intimate connection to Dean. Vanessa has some predictions for this new season, and we find out how Brittany really feels about the cast members after filming ended.

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Body Doubles Feb 11, 2019

Show notes

Things get “twinteresting” when Dean and Jared hang out with Brittany and Briana, who are identical twins engaged to another set of identical twins, Jeremy and Joshua. They tell us all about their adorable proposal story, and we find out how strong the “twin bond” actually is. You can follow their entire wedding adventure on “Our Twinsane Wedding” on TLC.

Then Dean opens up about his own fears of infertility, and how he’s confronting that anxiety.

And we discuss the new menstruation emoji, and how far texting can go before it becomes cheating.

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