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Dating Diaries: Questions and Confessions

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 ...
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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 Cali…
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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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at ht…
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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. See Privacy Policy at https://art19.com/privacy and…
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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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at htt…
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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 fo…
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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 prio…
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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 scooper…
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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.…
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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.
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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…
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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 Pri…
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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 …
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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 …
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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://a…
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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 Califor…
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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…
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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…
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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://art…
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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 Califor…
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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 htt…
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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 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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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 op…
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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 P…
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One new couple finds comfort in each other as they navigate personal hardships very quickly into their relationship. We also speak to a single who’s struggling to build a connection with a woman who is newly exploring her sexuality. And TikTok star, Lauren Saddington recounts a date she’ll never forget for all the wrong reasons, proving that going …
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Great sex and an Ivy League resume has one single hanging onto a relationship for dear life, despite his lack of communication. Another woman finds herself in a sticky situation after having more men than she can handle. And we speak to a single whose family creates a dating show to help their sister find a partner. See Privacy Policy at https://ar…
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This week we’re flipping the script and have some very special guests. Since no one knows you quite like your family, Andrea’s mom and twin sister join us to give an inside look at Dre’s dating life. 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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Dating Diaries follows one single woman, Lynette, through the dating jungle while she dodges dates who exaggerate, mislead and straight up lie. The experiences finally drive her to stop looking for love altogether. Then, after meeting a charming couple, she rethinks the idea of seeking a partner and an open heart yields rewards she didn't think she…
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What happens when your friend takes over texting on your phone with a potential new love interest? Nothing good. Plus, one single figures out that COVID concerns may be just be a cover for bad habits. And finally. when all else fails, this guy finds a new way to date in the most public way. See Privacy Policy at https://art19.com/privacy and Califo…
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This week on Dating Diaries we hear of stories that cross the borderline, literally and figuratively. From a woman who treks 4,500 miles to reunite with her love to another who explores a new dating territory. And on top of that Dre and Ben unpack one of our craziest dating experiences yet! See Privacy Policy at https://art19.com/privacy and Califo…
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A single discovers her date has been to her place before with someone else in a really strange way. Season 1 favorite Theresa, a COVID healthcare worker, needs her medical skills for an emergency at home. And does LOVE mean learning to embrace your inner Michael McDonald? Experience all of the dating highs and lows with Dre and Ben without ever lea…
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Dre and Ben are back for Season 2. Some of us may be out of quarantine but life and dating is still a challenge as we adjust to our new normal. Dre and Ben dig in to fresh stories about singles looking for love in strange times. The hosts are haunted by an unprecedented ghost story. And we hear from a listener favorite who delivers an update and (a…
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Relationship therapist Dr. Nedra returns to illuminate the benefits of a crisis on love and personal growth. Plus, Dre & Ben sing Hamilton's praises. 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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We went to the mailbag. Listeners wrote in and brought tough questions to Dre and Ben for the candid, compassionate feedback that we've come to expect. We hear from a musician who can't get a moment of privacy, a woman who is flashes her hot connection then gets ghosted and a seriously infatuated guy who sends a milkshake to the yard of his love in…
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When you need a safe word to stay platonic, can you still really call yourselves "friends?” We speak to a single who has got it pretty bad for someone that is unavailable. Dre and Ben unpack how to handle major cultural differences and the importance of what it means to be truly invested in someone else. And government guidelines for safe sex durin…
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Loving the same TV show or band can jump start a relationship, but will it endure? Plus, is that a doctor in those scrubs or is he just playing one on Tinder? 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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States are reopening and singles are trying to figure out if traditional dating will go back to the way it was or Facetime dates are here to stay. Another single experiences quarantine with her boyfriend and his family, despite barely knowing one another. And, we also hear from show favorite Reno who has a message for Ben. See Privacy Policy at htt…
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When we started this podcast, it was to provide an escape in a difficult time. We were all in quarantine, everything was so uncertain. And it still is. The show became a platform for sharing stories about personal relationships, showing up for one another and encouraging difficult conversations. We felt that proceeding with a new episode this week …
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We hear back from Kate about the excuse she got from a guy who blew her off. Dre and Ben also dig into a question from a listener whose date ending in a 3 mile walk home. 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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This week we hear from people moving in, moving away, and moving together. We check in with Theresa to see how things are going with her subway beau, a new single talks about how unhealthy social media can be during a mid-pandemic breakup and we hear from someone who is keeping sparks flying from thousands of miles away. See Privacy Policy at https…
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Love in the time of COVID is affecting people of all ages. Whether you’re a parent, dating a parent, or you had to move back in with your parents, each scenario breeds its own challenges. We'll also hear back from a familiar voice and her PSA on unsolicited explicit pictures and why no one wants them. If you have a question or quarantine confession…
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Ben's mom joins for this bonus episode. Dr. Nedra Fetterman is a renowned relationship therapist and licensed psychologist. Dre gives an update about her most recent ghosting experience and Dr. Fetterman shares some insight into the deeper reasons why people ghost. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at htt…
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Being isolated away from your friends and family can be really tough but we talk to singles who are finding the benefits to spending time with yourself. People are learning new skills, designating private spaces, and finding ways to be more comfortable with themselves. Dre and Ben delve into the power of focusing on yourself and Dre shares her own …
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Andrea and Ben revisit the step over text with a new listener question and talk about bargaining with yourself and breakups in quarantine. If you’d like your question answered on a future episode, email us about your quarantine dating situation at datingdiariespod@gmail.com. See Privacy Policy at https://art19.com/privacy and California Privacy Not…
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