#29 From Matchmaker to Marriage

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

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Single Parents with Kimrie Lewis1:23:43

13h ago1:23:43

1:23:43

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 ...…

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

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I Used to Be a Cougar with The Bubbies1:14:25

8d ago1:14:25

1:14:25

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 ...…

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

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Baecations with Dax Holt1:23:45

14d ago1:23:45

1:23:45

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 ...…

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

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Alter Egos1:40:41

22d ago1:40:41

1:40:41

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... Bar ...…

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

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Your Chairlift or Mine?1:15:44

29d ago1:15:44

1:15:44

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 ...…

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

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Body Doubles1:30:32

1M ago1:30:32

1:30:32

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 Weddi ...…

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

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Real Relationships & Fake Accents with Rob Mack and Naz Perez1:14:56

1M ago1:14:56

1:14:56

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, ...…

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

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Sister from Another Season with Kristen Doute1:37:57

2M ago1:37:57

1:37:57

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 ...…

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

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Into the Freezer with Whitney Bischoff1:13:38

2M ago1:13:38

1:13:38

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 ...…

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

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Feeling Tempted with Chad Johnson1:46:05

2M ago1:46:05

1:46:05

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 ...…

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

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On Matters of Sex1:19:15

2M ago1:19:15

1:19:15

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 ...…

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

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Dean's Homecoming1:30:59

3M ago1:30:59

1:30:59

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 (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 ge ...…

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

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Trust Your Gut1:24:01

3M ago1:24:01

1:24:01

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 (exclusivematchmaker.net) stops in to share some tips on how to t ...…

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

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Surviving the Ultimate Sucky Date1:17:17

4M ago1:17:17

1:17:17

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. Sh ...…

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

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Getting Intimate1:28:02

4M ago1:28:02

1:28:02

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.An ...…

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

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Q & A Day1:25:13

4M ago1:25:13

1:25:13

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 (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 communi ...…

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

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#55 We All Have Our Flaws1:09:10

4M ago1:09:10

1:09:10

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”. Vaness ...…

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

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#54 Let's Get it Together!1:02:56

5M ago1:02:56

1:02:56

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 spoke ...…

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

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#53 Girl Talk1:17:23

5M ago1:17:23

1:17:23

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 vis ...…

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

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#52 Sometimes You Have to Disconnect to Connect1:12:12

5M ago1:12:12

1:12:12

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 ...…

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

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#51 The Bugaboos1:10:52

5M ago1:10:52

1:10:52

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 ta ...…

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

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#50 Sex Ed1:16:02

6M ago1:16:02

1:16:02

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 g ...…

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

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#49 Pool Party46:50

6M ago46:50

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 ...…

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

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#48 Brainspotting1:10:40

6M ago1:10:40

1:10:40

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 t ...…

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

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#47 Like Apples and Onions1:13:20

6M ago1:13:20

1:13:20

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 y ...…

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

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#46 Stuck in a Trance1:14:00

6M ago1:14:00

1:14:00

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 co ...…

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

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#45 I Ain't 'Fraid of No Ghosts1:09:53

7M ago1:09:53

1:09:53

Dean, Jared and Vanessa head right into the haunted house, to see why people ghost each other. Elle Huerta from the Mend app calls in to help us understand the motivations behind ghosting, and has some tips on how to end relationships in a responsible way. And do you know what “zombie-ing”, “cushioning” and “orbiting” are?? It may be happening ...…

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

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#44 Leading On and Breaking Up with Taylor Nolan1:05:40

7M ago1:05:40

1:05:40

Taylor Nolan is hanging out with Dean, Vanessa and Jared this week, and she’s ready to tell all about her recent break up with Derek Peth. She and Dean give an exclusive look behind the scenes of what really goes down during Paradise, and she explains the one sentence that can help anyone going through a break up. And Jared, Dean and Vanessa ge ...…

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

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#43 Man with a (Wedding) Plan1:03:40

7M ago1:03:40

1:03:40

Jared is deep into wedding planning, and he's here to give Dean and Vanessa a full update on the search for a venue, and opens up about how Ashley's changed since they got engaged. Dean confronts Jared about not getting a plus one to the big day, and hear his honest thoughts on the comparison of Colton and Tia to Dean and Kristina on Paradise. ...…

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

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#42 Welcome Back Unglert1:13:47

7M ago1:13:47

1:13:47

Dean is finally back after his whirlwind trip around the world!We find out the deeply personal lessons he learned about himself, and about dating while on his trip. Plus, he shares a traveling habit that will make you question everything.And then Holly Martyn stops by, to talk about how her life changed when she challenged herself to go on 100 ...…

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

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#41 Make Do and Mend1:12:56

8M ago1:12:56

1:12:56

Jared and Vanessa tackle the difficult topic of how to recover from a break up, so they brought in Elle Huerta, who created the “Mend” app, which offers tools and support for people having a tough time splitting up. You have to hear some of the easy tricks she’s learned for how to beat the temptation to call an ex. Then, Bill Freeman and Sonya ...…

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

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#40 Flipping the Switch1:18:53

8M ago1:18:53

1:18:53

Jared is officially in wedding planning mode, and he shares some ideas he’s had for his bachelor party, and also reveals a few of the names from Bachelor Nation that will be on his wedding guest list. From “The Seven Year Switch” on Lifetime, Charles J. Orlando stops by to give Jared and Vanessa some valuable advice about honesty and communicat ...…

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

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#39 Return of the Stanger1:24:59

8M ago1:24:59

1:24:59

Millionaire matchmaker Patti Stanger is back! She gives Vanessa some incredible dating advice that she desperately needs. She confronts Jared about what she heard about him from Ashley, and he fires back at Patti for saying he and Ashley don’t belong together. Then Greg Behrendt and his wife Amiira Routola, the authors behind “He’s Just Not Tha ...…

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

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#38 Engagement Fast Track1:04:14

8M ago1:04:14

1:04:14

Jared, who is recently engaged himself, sits down with LisaReye and Anthony, who got engaged on last night’s episode of The Proposal on ABC. They talk about what it was like to make such a huge decision after a short amount of time, and how different the dating landscape is in 2018.Then Vanessa joins in to talk about another quick proposal, fro ...…

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

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#37 Put a Ring on It1:14:54

9M ago1:14:54

1:14:54

Jared is back after getting engaged to Ashley, and he’s got all the details on what went down, including some secret details about her ring.Dean gets Jared to spill some steamy secrets about his post engagement love life, and the guys give a behind the scenes look at the breaking news that Derek Peth and Taylor Nolan have split up.Then, they re ...…

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

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#36 Fast Food Sex59:13

9M ago59:13

59:13

Dean and Vanessa discuss how they were blown away by Jared and Ashley’s engagement news, and we get an update on Vanessa’s love life, as well as a look into some dates that Dean has been going on.Then they sit down with human relationship exper Dr. Wendy Walsh, and she gives Dean an honest look at his “marriage readiness”.We also find out the t ...…

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

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#35 Break Up Like a Pro59:34

9M ago59:34

59:34

Dean, Jared and Vanessa discuss the whirlwind relationship of Ariana Grande and Pete Davidson, and Jared tells us if he’s ready to take his relationship to the next level.Then they’re joined by Chelsea Leigh Trescott, a break-up expert, for some help on how to not suck at breaking up.And, after reflecting on their experiences with The Bachelor, ...…

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

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#34 Exes & Friends1:12:13

10M ago1:12:13

1:12:13

Dean, Vanessa and Jared talk about if you should be friends with your ex, and Dean shares his policy of blocking all his exes on social media.Then they recap the new episode of The Bachelorette, and Dean offers some inside info on the drama between Colton and Tia. And Jared shares a very intimate detail about his relationship with Ashley. Learn ...…

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

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#33 Dirty Dancing1:26:09

10M ago1:26:09

1:26:09

Jared opens up to Vanessa about a recent Hawaiian vacation with girlfriend Ashley. He spills all the details on the romantic getaway and the compromising position housekeeping caught them in! Author, Heather Monahan, calls in. She and the gang discuss confidence in dating, and how Vanessa can apply it to her own love life. And Dean still sucks ...…

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

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#32 Love Club1:00:34

10M ago1:00:34

1:00:34

After keeping it under wraps for months, Jared talks about a huge emotional breakthrough, and tells Vanessa and Dean who he’s dating, which leaves everyone in tearsThen they talk to matchmaker Kailen Rosenberg from “The Lodge Social Club” about dating apps, and opening a club for single people to meet and find love. Learn more about your ad-cho ...…

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

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#31 Camp Crushes1:23:16

10M ago1:23:16

1:23:16

Jared and Vanessa learn about “Camp No Counselors”, where you can play like a kid, and party like an adult. Then on the other side of the spectrum, venture capitalist Jesse Draper with the ultimate advice on how to avoid financial arguments when starting a new relationship. And if you’ve ever wanted to be on The Bachelor, you won’t want to miss ...…

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

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#30 Dating Etiquette1:13:12

10M ago1:13:12

1:13:12

Dean addresses the rumors that are swirling around about who he may or may not be romantically involved with, now that he’s single.Then, Vanessa and Dean sit down with Julian Clark from EVite, who is an expert in dating and party etiquette. He teaches Dean and Vanessa what to do if you run into an ex, and how to “ghost” a party.And Alexis Water ...…

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

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#29 From Matchmaker to Marriage1:06:25

11M ago1:06:25

1:06:25

Vanessa, Dean & Jared dive in head first to try and figure out the best way to meet somebody.Right off the bat, Matchmaker Tammi Pickle calls in, and since she works with successful and wealthy clients, she knows the most effective ways to meet a quality partner. Then, Dean’s friends Tiffany Au and Caleb Remington stop by the studio, to share h ...…

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

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#28 Sucking at Dating North of the Border1:08:33

11M ago1:08:33

1:08:33

Vanessa Grimaldi joins Dean and Jared in the studio this week, and she reveals something about her dating life she hasn’t told anybody before.Jared spills some behind the scenes info on what went down on Bachelor in Paradise Australia, and they talk to Life Coach Gina Kloes, who helps explain the stages of grief, and how that can help getting o ...…

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

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#27 Group Therapy1:29:36

11M ago1:29:36

1:29:36

Dean and Jared are joined by Amanda Stanton, who gives her honest feelings about what’s going on between her and Robby Hayes.Life Coach Cherie Healey calls in, to help Dean navigate the world of the recently single, and to see how his venture into therapy is going.And then Dean, Jared and Amanda reveal their biggest dating “dealbreakers”. Learn ...…

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

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#26 What's Inside My Head?1:29:25

11M ago1:29:25

1:29:25

Jared Haibon and Dean dive right in with the elephant in the room – Dean’s break up with Lesley Murphy. Together, they talk about what ended the relationship, and how he’s feeling after breaking up. Then, they continue on the path to improving at dating, by inviting psychic Reginald Lewis into the studio, for a reading on what is going on with ...…

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

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#25 More or Les with Dean56:34

12M ago56:34

56:34

Dean’s back! And he’s joined by his girlfriend Lesley Murphy for a deeper look at the world of dating.Erica has a dilemma – she’s developed a crush on her oral surgeon! How do you make a move after treatment has ended?Then, they tackle some listener emails, like what to do when a guy you like asks for your friend’s number, and if Dean felt like ...…

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

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#24 Kendall & Jared1:23:31

12M ago1:23:31

1:23:31

Kendall Long from Arie’s season of The Bachelor, and Jared Haibon from Kaitlyn’s season are the guest hosts this week, and ready to find out how to suck less at dating.After admitting their biggest relationship insecurities, they call on the help of Cherie Healey, a “possibilitarian” and Life Coach, to help find ways to open up, and how to find ...…

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

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#23 Big Time Dating57:31

12M ago57:31

57:31

James Maslow is in for Dean this week!After getting an update on what’s new in his world, and his experience on Celebrity Big Brother, James offers up his most valuable dating advice. Then, he helps some listeners out that are dealing with real dating struggles, like how to get past 3 dates, and if men should use emojis. Learn more about your a ...…

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

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#22 Ask Dean Anything47:56

1y ago47:56

47:56

Now that Dean is free from the shackles on contractual secrecy... he's answering your questions! And his girlfriend Lesley Murphy is hanging out to help field some burning questions about Winter Games, the Bachelorette, and beyond! Learn more about your ad-choices at https://news.iheart.com/podcast-advertisers…

Help! I Suck at Dating with Dean, Vanessa and Jared « »
#29 From Matchmaker to Marriage

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Help! I Suck at Dating with Dean, Vanessa and Jared « » #29 From Matchmaker to Marriage

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Help! I Suck at Dating with Dean, Vanessa and Jared « »
#29 From Matchmaker to Marriage