HELP! I Suck at Dating

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979 episodes
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Episodes979

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Jun 26, 2018 · 1 hr 14 min
#37 Put a Ring on It
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 recap this week’s Bachelorette episode, and we find out if Jared and Ashley will get married on TV. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Jun 19, 2018 · 59 min
#36 Fast Food Sex
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 test that Vanessa put every guy through on the first date. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Jun 12, 2018 · 59 min
#35 Break Up Like a Pro
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, they talk about if it’s okay to date a friend’s ex. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Jun 5, 2018 · 1 hr 12 min
#34 Exes & Friends
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 more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
May 30, 2018 · 1 hr 26 min
#33 Dirty Dancing
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 at dating whether he lives in a small town or the big city. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
May 23, 2018 · 1 hr
#32 Love Club
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 tears Then 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-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
May 15, 2018 · 1 hr 23 min
#31 Camp Crushes
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 when Allison Kaz calls in. She’s casting a new show for Fox that’s kind of like a “grown up” version of The Bachelor. She’s looking for ladies that are sick of dating and are ready to start a family with a serious partner. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
May 9, 2018 · 1 hr 13 min
#30 Dating Etiquette
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 Waters (is she a shark or a dolphin?) hangs out to share how she stopped sucking at dating, and met the man of her dreams. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
May 1, 2018 · 1 hr 6 min
#29 From Matchmaker to Marriage
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 how they made their wedding “The Greatest Wedding Ever Donated”. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Apr 24, 2018 · 1 hr 8 min
#28 Sucking at Dating North of the Border
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 over a breakup. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Apr 17, 2018 · 1 hr 29 min
#27 Group Therapy
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 more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Apr 10, 2018 · 1 hr 29 min
#26 What's Inside My Head?
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 Jared and Dean spiritually. Next, Matchmaker Nora DeKeyser calls in and offers some tips on the best way to find a quality match, and what to look for in your partner. And they wrap up with some listener emails, and give their advice on what to do if you and your friend are interested in the same person, and if you can have a future with someone if you have political differences. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Apr 3, 2018 · 56 min
#25 More or Les with Dean
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 his family was exploited on The Bachelorette. And, the group talks about “What Makes Us Weird”. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Mar 28, 2018 · 1 hr 23 min
#24 Kendall & Jared
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 balance between friends and relationships. Then, Kendall and Jared offer some listeners their advice on what to do when you’re caught up in a love triangle with friends, and how to handle an aggressive coworker. They wrap up with a rapid fire Q & A, and we find out where they stand on ghosting, blind dates, and how long to wait before having sex. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Mar 21, 2018 · 57 min
#23 Big Time Dating
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 ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Mar 13, 2018 · 47 min
#22 Ask Dean Anything
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://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Mar 6, 2018 · 1 hr 15 min
#21 Let's Hug it Out
Dean talks all about opening up and the benefits of hugging with Justin McMillen, the founder and CEO of Tree House Recovery. And this week is ripe with Bachelor drama after the season finale, so Dean and Erica do a full expert review how things wrapped up with Arie. Then, they read some listener emails, and Dean gives a behind the scenes look at what happened during Winter Games. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 26, 2018 · 1 hr 25 min
#20 Viall to the Rescue
Dean is out this week, but his buddy Nick Viall is happy to step in as guest host! He starts off the show by sharing what he thinks makes a good first date, and the phenomenon that is Black Panther. Then, he takes a trip to the world of meditation, when experts Sukey and Elizabeth Novogratz call in to offer advice on treating anxiety. But don’t worry, your emails are in good hands! Nick lends his opinion on getting back together with an ex, and he shares his concept of “Sour Patch Kid” relationships. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 20, 2018 · 44 min
#19 Dean's Friends from Camp
As Bachelor Winter Games is in full force, Dean brings his new friends from Vermont to the podcast! He’s joined by Courtney Dober, Kevin Wendt, and Lesley Murphy. They relive some memories, and get to know each other better as all corners of Bachelor Nation meet! Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.
Feb 14, 2018 · 1 hr 16 min
#18 Dating Sucks at Any Age
Dean is joined this week by his friend from Bachelor Winter Games, Courtney Dober, from Bachelorette Australia. The two get a dose of dating advice from matchmaker Carmelia Ray, from the Myx TV show “Mom vs Matchmaker”. Then, for a different perspective at finding love, they hear from Julie, who is 74 years old and very much on the dating scene. Dean is delighted to read some listener emails, including some ideas for a new show name, how to date someone who doesn’t drink, and he and Courtney give some tips on how to audition for The Bachelor. Learn more about your ad-choices at https://www.iheartpodcastnetwork.com See omnystudio.com/listener for privacy information.