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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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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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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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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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!

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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. 

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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.

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.