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HELP! I Suck at Dating

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HELP! I Suck at Dating

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iHeartPodcasts

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Podcast website

www.iheart.com

Latest episode

Jul 11, 2026

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Episodes

Single Parents with Kimrie Lewis 19.03.2019

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...

I Used to Be a Cougar with The Bubbies 12.03.2019

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 int...

Baecations with Dax Holt 04.03.2019

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 fr...

Alter Egos 25.02.2019

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! Learn more about your ad-c...

Your Chairlift or Mine? 18.02.2019

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”.   T...

Body Doubles 11.02.2019

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...

Real Relationships & Fake Accents with Rob Mack and Naz Perez 06.02.2019

Vanessa recently made it Instagram official with her new boyfriend, and she’s ready to open up to Dean and Jared about why this might be her most serious relationship yet.   Then Rob Mack from Famously Single on E! stops by. He’s a “love coach”, and once we find out what that is, he tells us all about how to find true happiness in a relationship, and he spills about some of the celebrity couples h...

Sister from Another Season with Kristen Doute 28.01.2019

Kristen Doute from Vanderpump Rules stops by to hang with Dean and Vanessa… and she brought wine! After a couple glasses of her new “Witches of Weho” wine, she lets us in about some of the hookups that go down on the new season of Vanderpump Rules, and she bonds with Dean and Vanessa over life on reality TV.  Then we take a trip to the sunshine state, with Madisson Hausberg from Siesta Key! We tal...

Into the Freezer with Whitney Bischoff 21.01.2019

This week everyone focuses on an extremely important part of Vanessa’s anatomy… her ovaries. Vanessa’s been exploring the topic of freezing her eggs, so we talk to Bachelor alum Sadie Murray , who actually froze her eggs. She was also the original “Bachelor virgin”, so we get her take on Colton’s season and the unending virginity talk.   Then, we talk to Whitney Bischoff from Chris Soules’ season,...

Feeling Tempted with Chad Johnson 15.01.2019

Dean addresses his bombshell interview with Access Live and explains why he said Bachelor relationships aren't real.  Jared, who is in a Bachelor relationship of course disagrees with Dean, and they fight it out on the air. Then, former  Bachelorette contestant, Chad Johnson from  MTV's “Ex on the Beach” is coming by the studio.  Dean is NOT happy about it and considers not participating in the in...

On Matters of Sex 08.01.2019

Dean is back from the land down under, and he’s ready to talk all about everyone’s favorite subject… SEX. Dr Chris Donaghue, author of the book "Rebel Love", stops by to clear up some misconceptions about sex, including a MAJOR misunderstanding Dean has about the female anatomy.  We answer your burning questions, and some of them get REALLY down and dirty.  Then, we find out something about one of...

Dean's Homecoming 18.12.2018

Dean’s back from his trip to South America! He’s got a bunch of stories from his adventures, and he finally some news from his dating life! Then, we hang out with relationship expert Hillary Goldsher (drhillarygoldsher.com), for some advice on how to get the most out of therapy. She also has some valuable resources people can check out before getting started with therapy. And she sticks around to...

Trust Your Gut 11.12.2018

Vanessa wants to clear up some rumors that have been circulating about her romantic life with a member of Bachelor Nation, and we hear about Jared’s experience as a Chippendale’s dancer, and his first time being spray tanned. Then matchmaker and relationship expert Susan Trombetti (exclusivematchmaker.net) stops in to share some tips on how to tell if you’re being cheated on, and how to know you’r...

Surviving the Ultimate Sucky Date 03.12.2018

Jared and Vanessa meet up to talk about Lauren Bushnell’s new boyfriend, country singer Chris Lane, and it leads to a conversation about if you should give an ex a heads up before “going public” with a new relationship. Then Youtuber Brittani Louise Taylor stops by, and shares her absolutely wild story about the worst relationship in history. She has some dating lessons she learned from being invo...

Getting Intimate 26.11.2018

This week, Dean and Vanessa are ready to get real about sex. Intimacy expert Alanna Pratt is on to help Vanessa work through a situation with her recent ex, and they discuss if monogamy can actually work in a relationship.  Dean opens up about his love life, and we hear the (sometimes) awkward argument of why Vanessa thinks she’s great in bed. And she spills a few secrets about the more intimate m...

Q & A Day 13.11.2018

This week, Dean, Vanessa and Jared are answering all the questions listeners have submitted to them over social media. And here to help them make sense of it all is Possibilitarian Cherie Healey (www.cheriehealey.com). She helps us understand what it means to be “stuck in your own head”, and she really helps Dean figure out what type of communication is appropriate with an ex. Jared opens up about...

#55 We All Have Our Flaws 05.11.2018

Dean, Vanessa and Jared talk about the big news in Bachelor Nation: the break-up of Shawn Booth and Katilyn Bristowe. They each have a unique perspective, because Jared is friends with Shawn, Vanessa is friends with Kaitlyn, and Dean knows nothing about either one! Then, our podcast threesome talks about Frankie Grande and his “throuple”. Vanessa recently admitted she’d try a threesome, but would...

#54 Let's Get it Together! 30.10.2018

Dean, Vanessa and Jared gets some life altering tips on how to remove stress and anxiety from their lives from Lauren Berger, who is the author of the book “Get it Together!”. She also has some advice on how to better handle rejection, which anyone who is in the dating world can benefit from. Then Dean wants to reach out to an ex he hasn’t spoken to since they broke up. What’s the etiquette on tha...

#53 Girl Talk 22.10.2018

Vanessa gets honest and real in this episode, and talks all about the new man in her life, and how she felt "fighting the fizzle" in her last relationship. And she really opens up about the incredibly emotional topic of having kids. But she's got some help to lead her in the right direction, when Elle from the Mend app stops by, and we get a visit from Dr. Jennifer Freed, a psychological astrologe...

#52 Sometimes You Have to Disconnect to Connect 15.10.2018

Dean and Vanessa learn all about the troubles with tech addiction from Jedidiah Bila, who just wrote a book about taking back your life from your cell phone. She tells this INSANE story of finding her boyfriend had a totally separate life that she didn’t know about, until she looked through his phone. Then we hear from matchmaker Susan Trombetti, who has advice for how women can stay safe while da...

#51 The Bugaboos 08.10.2018

Dean, Jared and Vanessa are bringing in the big guns this week, and have 2 major experts in matchmaking to help everyone suck less at dating. We talk to Pastor Cal from Married at First Sight, about the most important factors that make up successful relationships, and he gets real about how important personal faith is in relationships. Then we talk to Eileen from Elite Connections, and she shares...

#50 Sex Ed 02.10.2018

This week, we’re getting down and dirty about sex! YouTube superstar Laci Green is hanging out to give some much needed advice to Dean and Jared about how to have better sex, and she gives Dean some pointers on how to dirty talk. And, she gets Jared to open up about his sex life with Ashley! Then, Jared and Dean discuss if it’s ever helpful to go on “a break” when you’re having relationship troubl...

#49 Pool Party 22.09.2018

Dean and Jared are live from the pool at the Planet Hollywood Hotel and Casino in Las Vegas! It gets rowdy when Jason Tartick stops by, and we hear about what it’s like dating after The Bachelorette, and what his go to “opening line” is.  And Blake Horstmann is hanging out too, and he spills the best way to get him to respond to a DM.  Then we do a round of Rapid Fire Questions: Vegas edition.  Le...

#48 Brainspotting 18.09.2018

We have a big surprise in store for Dean this week, and it puts him face to face with one of his biggest passions. Then, we get therapist Haley Hewitt in studio, for a brainspotting session with Dean. We hear the results of their off-air meeting, and he has a huge breakthrough about his past that helps him understand his behavior.   And we talk to Samantha Hess, who is a master cuddler, about the...

#47 Like Apples and Onions 11.09.2018

Taylor Nolan is back to dish about what went down during her trip to Camp Fireside with Vanessa. We hear all about the new man in her life that may convince her to move to Canada. Then, Dean and Vanessa talk to Haley Hewitt, a marriage and family therapist. She helps explain the effects of traumatic experiences, and she offers some simple tips you can follow to improve your mental health. And Tany...

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