Help! I Suck at Dating with Dean, Vanessa and Jared show

Help! I Suck at Dating with Dean, Vanessa and Jared

Summary: Dean Unglert has called in some backup for his quest to become better at dating, and who better to help than friends who have dated and broken up on television! Vanessa Grimaldi and Jared Haibon are Dean’s cohosts on the all new Help I Suck at Dating, and between the 3 of them, they might have a chance at finding out the secrets to a successful relationship. They’ll talk to love experts, psychics, celebrities, and everyone in between that can help make them better partners. It’s the all new “Help I Suck at Dating with Dean, Vanessa and Jared” an iHeartRadio podcast.

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 Dean's Homecoming | File Type: audio/mpeg | Duration: 01:30:59

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 (, 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 lend her expertise to some relationship questions from our Facebook page. Plus, Vanessa tells us why she thinks she’s in her sexual prime, and we hear what Dean thinks about using sex toys. Brought to you by: AMAZON FIRE TV - Head to to order a Fire TV of your very own STAMPS.COM - Enter dean for a special 4 week Trial THRIVE MARKET - Take an EXTRA 25% off your first order + free 30 day trial at THRIVEMARKET.COM/DEAN THIRD LOVE – Go to now to find your perfect-fitting bra… and get 15% off your first purchase! 23ANDME - get 30% off any 23andMe kit. Order your DNA kit at

 Trust Your Gut | File Type: audio/mpeg | Duration: 01:24:01

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 ( stops in to share some tips on how to tell if you’re being cheated on, and how to know you’re getting to know the “real” person you’re dating. Plus, she’s a Bachelor fan! She shares her expert analysis on Vanessa’s break up with Nick. And we hear some intimate details about Vanessa, her bedroom, and costumes.

 Surviving the Ultimate Sucky Date | File Type: audio/mpeg | Duration: 01:17:17

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 involved with a manipulative and dangerous person. And she helps break down the differences between dating apps, and when is the best time to tell someone you’re dating that you have a child.

 Getting Intimate | File Type: audio/mpeg | Duration: 01:28:02

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 moments she shared with Nick Viall.

 Q & A Day | File Type: audio/mpeg | Duration: 01:25:13

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 ( 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 his plans with Ashley after they get married, and the group gives some really great advice for dating as an introvert. 

 #55 We All Have Our Flaws | File Type: audio/mpeg | Duration: 01:09:10

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 she be into a “threelationship”? And we get Dean’s honest thoughts on what’s going on between Blake Hortsmann and Kristina Schulman.

 #54 Let's Get it Together! | File Type: audio/mpeg | Duration: 01:02:56

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 that?? Should it ever be done? And Vanessa spills some secrets about what she’s open to “intimately”, and we hear about Jared’s first visit to a sex shop.

 #53 Girl Talk | File Type: audio/mpeg | Duration: 01:17:23

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 astrologer. She gives Vanessa some incredible advice on what she needs to do to meet her future husband. And her friend Brandi Cyrus hangs out too, to talk about her experiences on dating apps, and what it's like moving to Denver, Colorado, a city with a TON of single guys. 

 #52 Sometimes You Have to Disconnect to Connect | File Type: audio/mpeg | Duration: 01:12:12

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 dating, and some simple tips to avoid putting yourself in dangerous situations. And we get a long awaited and in depth update on the new man in Vanessa’s dating life!

 #51 The Bugaboos | File Type: audio/mpeg | Duration: 01:10:52

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 the rules she’s come up with for your relationship to last. She tells us how important it is to be friends first with people you date, and explains how emojis can kills relationships. And we do a round of rapid fire dating questions with Dean and Vanessa, and hear about who they’ve been dating.

 #50 Sex Ed | File Type: audio/mpeg | Duration: 01:16:02

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 troubles, and we hear about what it was like when their names first got released for The Bachelorette.

 #49 Pool Party | File Type: audio/mpeg | Duration: 00:46:50

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. 

 #48 Brainspotting | File Type: audio/mpeg | Duration: 01:10:40

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 world of professional cuddling and she fills us in on the best ways to cuddle. Plus, we get a full recap of Dean’s date with Tanya Rad!

 #47 Like Apples and Onions | File Type: audio/mpeg | Duration: 01:13:20

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 Tanya Rad stops by to talk all about her upcoming date with Dean. 

 #46 Stuck in a Trance | File Type: audio/mpeg | Duration: 01:14:00

Runner up from Rachel's season of The Bachelorette Peter Kraus is hanging out with Dean, Vanessa and Jared, and we hear his take on how to confront a ghoster and how to know when you’ve met “your person”. Jared shares some incredible behind the scenes details from his proposal to Ashley, and he reveals a crazy secret about the ring! Then, Dean confronts some intense emotions when he works with Hypnotist Dr. Nancy Irwin. She shares some simple tips that everyone can use in their everyday lives.


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