HELP! I Suck at Dating

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979 episodes
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Episodes979

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Jul 10, 2023 · 50 min
Give Me Your Heart, Make it Real with Rob Thomas
Jared has re-entered the honeymoon phase with his new bromance! His idol Rob Thomas from Matchbox Twenty joins the Newlyweds to share some incredible advice from his 25 year marriage! Jared reveals the words of wisdom Rob gave him after he and Ashley got married, and we find out how that tip completely changed their relationship. Plus, we learn what Rob REALLY thinks of The Bachelor! See omnystudio.com/listener for privacy information.
Jul 3, 2023 · 15 min
Happy Fourth of July!
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Jun 29, 2023 · 25 min
Tossing the Q&A Bouquet
The Newlyweds are back for another round of Q&A and NOTHING is off limits! Things get tense when Dean admits why he never felt like he was “in love” until recently! Caelynn reveals how she manifested her relationship with Dean, and Jared shares his true hopes for baby #2! Does he want a boy or a girl?? See omnystudio.com/listener for privacy information.
Jun 27, 2023 · 36 min
For Whom the Bell Tolls
Dean and Caelynn fill us in on a MAJOR life decision they made at 3 AM in Bali… and Jared doesn’t know how to react. Jared opens up about a frustrating parent moment while trying to build a bike for Dawson. Is it possible to never show anger in front of your child?? And, Dean and Caelynn let us in on a wedding plan that could leave a permanent impact on their guests! See omnystudio.com/listener for privacy information.
Jun 22, 2023 · 33 min
90 Day Mountain Climbing Fiancé
The final countdown is on for Dean and Caelynn’s wedding, and Dean is hard at work to prove there ain’t no mountain high enough to keep him from Caelynn. The Newlyweds are answering all your questions! Find out who their first crushes were, how they express anger, and how they REALLY feel about thigh high boots. See omnystudio.com/listener for privacy information.
Jun 19, 2023 · 29 min
No Use Crying Over Spilt Paint
It’s Caelynn’s birthday! And no better way to celebrate than traveling with Dean for 20 HOURS. Will this trip be the final straw for Dean and Caelynn?? We’ll find out! Jared reveals that he and Ashley are planning to grow their family sooner than we thought! And, Caelynn opens up about the pros and cons of Dean’s handyman skills. See omnystudio.com/listener for privacy information.
Jun 15, 2023 · 23 min
A Tik Tok Marriage with Taylor & Sophia Watts
Social media sensations Taylor and Sophia Watts join the Newlyweds to talk all about getting married at a young age, sharing everything about their relationship on social media, and what happened when they started a family only 2 months after getting married! Hear the real story of the pressures that come with making your relationship public to millions of followers. And they have some crucial advice for Dean and Caelynn as they prepare to walk down the aisle! See omnystudio.com/listener for privacy information.
Jun 12, 2023 · 34 min
Venue Vendetta
Dean and Caelynn had a photoshoot at their wedding venue! You won’t believe the feelings that came up as they get closer to the big day. If you’re planning a wedding, you HAVE to hear the method Dean and Caelynn used to make one of the biggest decisions – the food! Plus, Dean reacts to the backlash he got for his refusal to celebrate their anniversary on their wedding day. Do you agree with Dean?? See omnystudio.com/listener for privacy information.
Jun 5, 2023 · 46 min
The Perfect Date
There's some tension between Dean and Caelynn on their wedding date! You won't believe Caelynn's reaction when she finds out when Dean plans on celebrating their anniversary! We get a sneak peek at where Dean and Caelynn are heading on their honeymoon. And, Dean reveals what happened when anothe reality tv star hit on Caelynn! See omnystudio.com/listener for privacy information.
Jun 1, 2023 · 27 min
Living in the Moment with Rydel Funk
Singer and actress Rydel Funk is expecting baby #3 and ready to share all the pregnancy and parenting tips to our Newlyweds! Find out the best kept secret when it comes to raising 2 kids under 2. And, we discuss the constant struggle of wanting to document every special moment with photos and videos, but also trying to be present and live in the moment. See omnystudio.com/listener for privacy information.
May 29, 2023 · 44 min
A Wing Walk to Remember
Relationships are all about compromise, so what will it take to get Caelynn on the back of Dean’s motorcycle?? Dean reveals his next big stunt, but Caelynn is NOT into the idea. Should you support your partner no matter what?? And, Jared shares Ashley’s change of heart when facing their decision to leave Rhode Island. See omnystudio.com/listener for privacy information.
May 25, 2023 · 37 min
Brady Beefing with Ria and Fran from Chicks in the Office
The Newlyweds meet the Chicks in the Office when Ria Ciuffo and Fran Mariano walk down the aisle! Things get TENSE when Ria shares her real thoughts on Tom Brady. And… do you think The Bachelor is coming to an end?? Dean, Caelynn and Jared discuss the future of the franchise with Ria and Fran. See omnystudio.com/listener for privacy information.
May 22, 2023 · 34 min
Mother’s Day No More
Jared has a controversial take: should Mother’s Day be CANCELLED?? He explains why he thinks we don’t need the holiday anymore. Caelynn reveals who does the heavy lifting in the intimacy department in her relationship with Dean, but it sounds like things are going well! Plus, we get a wedding update, and surprising no one, Dean is missing a MAJOR detail. See omnystudio.com/listener for privacy information.
May 15, 2023 · 49 min
Courthouse I Do’s
After all this build up, Dean and Caelynn almost got married LAST WEEK! Jared shares his take on a “courthouse wedding” and why Dean and Caelynn need to do it! Caelynn opens up about her fears and anxieties about her wedding dress, and we get a full recap of her dream bridal shower in Vegas! Plus, Jared lets us in on life as a single dad while Ashley is out of town… and he might toally lose it before she gets back. See omnystudio.com/listener for privacy information.
May 12, 2023 · 19 min
Nip(ple) it in the Bud
The newlyweds are answering your emails and they go to some strange places! We get into body hair removal and learn a little too much about Jared and Dean. And things get TENSE when sharing how their significant others "hold them back"! See omnystudio.com/listener for privacy information.
May 8, 2023 · 48 min
Cloudy with a Chance of Bridal Showers
The Newlyweds are stressing this week! Caelynn is getting ready for her bridal shower but some major people will be missing... and one of them happens to be Dean! Jared is dealing with single dad life after Ashley makes a last minute trip to Australia. And, find out why Dean and Caelynn might be parents sooner than you thought! See omnystudio.com/listener for privacy information.
May 1, 2023 · 1 hr 2 min
Hot, Not, or Botox
Do you think it’s hot when someone has a raspy voice?? You might be surprised at what Dean, Caelynn and Jared find hot in the opposite sex! We get into (too much) detail about what gets them going. Plus, could Dean and Caelynn be moving AGAIN?? Find out where they might be relocating to, and Jared reveals some of the challenges he faced moving from LA back to Rhode Island! See omnystudio.com/listener for privacy information.
Apr 24, 2023 · 1 hr 2 min
Brother to Mother
Caelynn and Dean are in the depths of wedding planning, and Caelynn has a shocking admission to make which brought her to tears. You won’t believe what’s on her mind! And, we set the record straight about Dean and Caelynn’s plans for a “genetically similar” sperm donor. See omnystudio.com/listener for privacy information.
Apr 17, 2023 · 40 min
High Fives over Low T
Dean and Caelynn share the results of their fertility tests, which could mean that a Bachelor baby is in the future! But... wait until you hear why Dean might NOT be the father! Plus, we get into all the details about our recent guest Lindsay Hubbard from Summer House and her "accidental hard launch" of Tayshia's possible new guy! See omnystudio.com/listener for privacy information.
Apr 13, 2023 · 27 min
The Newlyweds Bare All
Dean and Caelynn face off in the ultimate challenge: Who knows the other best?? Nothing is off the table as Dean and Caelynn answer intimate questions about each other, and it seems like Jared might know Dean better than his other half! Plus, you won’t believe WHY Dean strips down in the middle of the podcast! See omnystudio.com/listener for privacy information.