Dating Diaries: Questions and Confessions

Dating Diaries: Questions and Confessions

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.

Episodes

November 2, 2021 27 min

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. 

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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.

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October 19, 2021 26 min

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.

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October 12, 2021 26 min

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. 

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October 5, 2021 26 min

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.

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September 28, 2021 22 min

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 him...

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September 21, 2021 25 min

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 lov...

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August 17, 2021 25 min

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. 

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August 10, 2021 22 min

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.

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August 3, 2021 26 min

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.

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July 27, 2021 22 min

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?

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July 20, 2021 23 min

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? 

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July 13, 2021 25 min

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. 

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July 6, 2021 29 min

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.

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June 29, 2021 24 min

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.

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June 22, 2021 24 min

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.

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June 15, 2021 27 min

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. 

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June 8, 2021 30 min

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. 

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June 1, 2021 22 min

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. 

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May 25, 2021 24 min

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.

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