Episodes
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.
Published 11/02/21
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.
Published 10/26/21
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.
Published 10/19/21
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.
Published 10/12/21
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...
Published 10/05/21
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...
Published 09/28/21
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...
Published 09/21/21
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.
Published 08/17/21
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.
Published 08/10/21
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.
Published 08/03/21
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.
Published 07/27/21
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...
Published 07/20/21
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.
Published 07/13/21
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 our Privacy Policy at https://art19.com/privacy and our California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Published 07/06/21
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 our Privacy Policy at https://art19.com/privacy and our California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Published 06/29/21
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.
Published 06/22/21
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. 
Published 06/15/21
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. 
Published 06/08/21
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. 
Published 06/01/21
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.
Published 05/25/21
Dre and Ben return for Dating Diaries season 3 on May 25, 2021!
Published 05/21/21
Whether it’s moving to a new city after only a couple weeks, planning vacations or dreams of taking things to the next level, this week’s singles are just not on the same page as their partners.   See acast.com/privacy for privacy and opt-out information.
Published 10/14/20
It looked like love at first. A single from season one returns to the podcast to share her side of a whirlwind romance that turned toxic and what she learned about herself and relationships in the process. The contents of this show, Dating Diaries: Questions and Confessions, is for informational and entertainment purposes only. The commentary and opinions on this show should not be taken as professional advice.   See acast.com/privacy for privacy and opt-out information.
Published 10/07/20
We meet a woman who gets herself in a sticky situation with two guys who have a lot more in common than she bargained for. Is date two too soon to unpack sexual preferences? One single is left speechless after her date gauges her interest in his personal needs. One couple recounts their journey to love after a brief encounter on a dating app.    See acast.com/privacy for privacy and opt-out information.
Published 09/30/20