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Dating Diaries: Questions and Confessions

Dating Diaries: Questions and Confessions

Author: Glass Entertainment | Wondery

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Dating Diaries: Questions & Confessions unpacks the complexities and experiences of dating in today’s new normal. Singles and couples share their dating, relationship, and love stories. And the stories are from all over – a man who traveled from Nantucket to Columbia to find love, a woman who is convinced she had sex with an alien, a mid-twenties divorcé who is trying to get back out there after heartbreak, a couple that lived two doors down and ended up sheltering in place together for good, and a man who was so concerned he gave his partner COVID, only to find out that he was infected…with a venereal disease. We’re here for all of it. 

Dating Diaries: Questions & Confessions is hosted by your new best friends, Dre and Ben. Join them for new episodes weekly. 

55 Episodes
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Breadcrumbed

Breadcrumbed

2021-11-0227:412

A single in London looks like a total package on the outside but carries his schoolboy insecurities on the inside when it comes to women. Then, a single lady met a man through friends and sparks fly. When her new man suddenly employs a bread-crumbing strategy, she realizes he's just a player. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
House Arrest Sex

House Arrest Sex

2021-10-2623:391

This week we meet a man whose life choices limit his freedom and access to dating. But even with a mandated curfew, life throws him an unexpected gift. Then a single woman from Colorado walks out on a date when she’s asked to do something that’s out of the question.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Mouth Wide Open

Mouth Wide Open

2021-10-1926:411

A young woman shares how a traumatic experience with a date changed her outlook on more than just her love life. It was the beginning of a complete transformation. Then Andrea shares the deets on a recent relationship and why the ending showed the kind of growth that only experience can teach you.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Adult Exercise

Adult Exercise

2021-10-1227:18

A single mom finds a hot guy at a place she’d least expect to but decides to let him know she’s game for just about anything. Then, a woman exploring her bi-sexuality is baited into a trip away with a new love interest only to discover she’s been completely misled. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Easy Peasy

Easy Peasy

2021-10-0526:56

Singles are all looking for a spark, a connection, their “ying to my yang.” We want a definitive sign that says: "Yeah, that’s my person". But maybe it’s calm, unstated comfort and lack of drama that's key to a successful long-term relationship. This week, we’ll meet two singles who discovered a natural ease in their relationships that have made for a lasting and happy union.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
In The Delta

In The Delta

2021-09-2823:451

Change can be painful but it can also be beautiful. At the end of the day, it’s about what you learn in those transitional times. This week, our singles are both facing significant shifts in their relationships. Our first single still has conflicted feelings for a man whose behavior borders on emotional abuse. The second must decide whether to prioritize his new experience or his new relationship. Meanwhile, Ben is in the delta himself after a significant life change!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
We welcome Brooke and Aricia, the super hilarious co-hosts of EVEN THE RICH. On their podcast, Brooke and Aricia examine the personal lives of the rich and famous. So now we’re coming together for a very special episode of Dating Diaries, where we turn the tables and take a deep dive into their romantic lives. We’re getting the scoop on the scoopers. We’ll talk everything from the apps, to dating in LA, to falling in and out of love. Brooke and Aricia are BFFs and they’ll even dish about each other’s love lives for the first time ever. EVEN THE RICH hosts Brooke and Aricia join Dating Diaries and spill it all.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Dre and Ben respond to a listener’s plea for dating and profile advice. Then Dre and Ben hear from a girl whose own ghost story proves the old adage: when you least expect it. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Oui Oui Oui not I I I

Oui Oui Oui not I I I

2021-08-1022:322

On today’s episode we hear one of the worst date experiences imaginable. And our second single struggles finding a partner that checks the many boxes on her list.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Know When To Fold ‘Em

Know When To Fold ‘Em

2021-08-0328:001

Every good dater knows that the secret to survivin' is knowin' what to throw away and knowin’ what to keep. This week we hear a disaster date. Instead of walking away, our single doubles down for a good story. Then we hear from a woman who gambles on a DM slide and rekindles an old flame. Turns out her old beau folded the relationship for the wrong reasons.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Truth Hurts

Truth Hurts

2021-07-2724:171

One of our singles tries polite but direct communication when navigating a bad date with shocking results. And another finds herself working on finding herself after a heartbreak. Is a co-dependency on a new relationship that lacks passion preventing her from chasing her true goals?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Taking Applications

Taking Applications

2021-07-2024:521

Survey says that this week’s episode is great! Dre and Ben hear from one single looking for the perfect summer fling. But not just anyone will be the right Danny to her Sandy. All suitors must go through a rigorous application process. Then we hear one heart breaking story that makes us wonder….should there be a mandatory background checks process for dating these days? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Rules of Engagement

Rules of Engagement

2021-07-1327:14

We all have our own rules when it comes to dating and love. This week Dre and Ben explore what happens when you break those rules and what happens when you rewrite them. We hear from one single who dips her toe into office romance. While another single from across the pond explores new ways of navigating dating in a more empowered way. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Pumping The Brakes

Pumping The Brakes

2021-07-0631:321

Breaks, Break Up and Break downs. This week we are pumping the brakes and exploring do breaks really work? We hear from one single’s story of heartache and how she found herself in the breakdown. Finally, Dre and Ben hear from a single who is navigating dating and sexual experiences after surviving a traumatic event.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Two Doors Down

Two Doors Down

2021-06-2924:061

Often on Dating Diaries we only hear one side of the story. This week we get the benefit of both perspectives. We hear the story of Stacie and Alex, two neighbors who eyed each other up for months. Dre and Ben unpack the logistics and delicate dance of courting someone just two doors down.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Bone Appetite

Bone Appetite

2021-06-2225:281

Sometimes disappointment brings the greatest insights. This week Dre and Ben meet two singles rebounding from harsh realities. Connor learns about an STD in a pretty cold fashion. Sasha leaves a dog of a man to reclaim her health and dignity, which leads to her greatest mission in life.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
When Love Takes Root

When Love Takes Root

2021-06-1529:201

Call us saps but we enjoy a good romance! And this week Dre and Ben unpack two great love stories. One single goes out on a limb to follow his passion and finds love in the process. Amanda encounters a new suitor who seriously pines fir her. Instead of throwing him shade she embraces his strength when she most needed it. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Intentions

Intentions

2021-06-0831:441

Picture-perfect, these ladies don't need no filter. We hear from a widower that is setting intentions with a remote beau and getting her groove back. While our other single, Jessica, struggles to understand her new suitors’ intentions which leaves her terrified after one encounter and on shaky ground after another. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
When You Least Expect It

When You Least Expect It

2021-06-0124:351

Major life moments often happen when you least expect it. Whether it’s finding love, dealing with divorce or fighting for your life, you can never predict the timing. But how these events shape you - that lasts a lifetime. We hear from two women who were challenged and tested but overcame. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Cosmic Love

Cosmic Love

2021-05-2524:501

Dating Diaries is back with Season 3! In this episode, we hear what lengths people will go to find connection. When Joe runs out of dating options on his island and seeks love elsewhere. And we hear from Claire who has a dating experience that is out of this world.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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