Dating Diaries: Questions & Confessions

By Glass Entertainment Group

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Dating Diaries: Questions & Confessions unpacks the complexities and experiences of dating during the COVID-19 pandemic. The show will explore the minds, hearts and desperate measures of singles all over the country who are stuck at home, trying to find love and new ways to connect. Each week we will release an episode that features the unique perspectives of singles navigating this new age of dating. Dating Diaries: Quarantine Confessions is the podcast the country is craving right now. 

Episode Date
Nick of Time

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 leaving your house.


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Aug 12, 2020
Bonus: Cheeky

Dre and Season 1’s Kate and Mary talk about their speed dating experience through My Cheeky Date.


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Aug 10, 2020

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 (as always) gives Ben a hard time.


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Aug 05, 2020
Bonus: Friends with Benefits Situation

Dre and Ben dissect a listener's email regarding a complicated friends with benefits situation.


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Jul 20, 2020
Bonus: Never Waste A Crisis

Relationship therapist Dr. Nedra returns to illuminate the benefits of a crisis on love and personal growth. Plus, Dre & Ben sing Hamilton's praises.


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Jul 13, 2020
Bonus: Risk vs Fomo

Dre and Ben unpack listener emails.


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Jul 06, 2020
Can I Get an Amen?

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 interest with mixed results. Plus Dre confesses to sliding into someone's DM's after a few too many. 


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Jul 01, 2020
Bonus: A.F.G.O.

Dre and Ben talk to Dr. Nedra Fetterman about the anxiety and emotional complexities of reentry.


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Jun 29, 2020
Diversified Portfolios

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 during a pandemic?! Yep, Dre and Ben weigh in on that, too. 


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Jun 24, 2020
Bonus: Buzzin' Around

Dre and Ben review a listener's email.


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Jun 22, 2020
Survivor, Phish and Dr. Douche

This week, Dre and Ben are hearing more stories from people who are starting to brave the post-lockdown dating world. We hear everything from relationships budding from Survivor and Phish obsessions to fake doctors and more ghosting.


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Jun 17, 2020

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.


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Jun 10, 2020
Taking a Knee

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 as usual was not appropriate. This is a defining moment for our country to change the systemic racism that exists in America. It is important for us, as a production team, to take a step back and hold space for what is happening in our communities. Especially our home in Philadelphia. Finding the right words has been difficult. It’s important for us to be the audience this week. To listen and turn our attention to being better allies to the black community; by better educating ourselves, showing up, and having tough conversations with our neighbors, our friends and families that can no longer be ignored. So please let’s be better to one another and stay safe out there.


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Jun 03, 2020
Bonus: Too High to Hang

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.


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Jun 01, 2020

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.


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May 27, 2020
Red Zone

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 you want Dre and Ben to look at on the show, write to us at or Tweet us @DatingDiariesQC.


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May 20, 2020
Bonus: Ghostbusters

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.


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May 18, 2020
Ridin' Solo

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 quarantine confession.


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May 13, 2020
Bonus: Heartbreak and Murder Hornets

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


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May 11, 2020
Shit Gets Real

Singles are still trying to date and have fun in quarantine but what happens when situations get serious? Flings and FaceTime dates are one thing, but we talk to some singles who have found themselves staring down major dilemmas and others who have decided to take stay-at-home orders to heart. Dre and Ben break down their decisions and look at how people are handling it when shit gets real.


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May 06, 2020
Bonus: Step Over Text

Andrea and Ben talk about the “step over text” and give some advice to listeners who have sent in their quarantine confessions. If you’d like your question answered on a future episode, email us about your quarantine dating situation at


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May 04, 2020
Ghosted During a Pandemic

There’s never a good time to be ghosted. It always sucks. But we can all agree it’s even worse when you don’t have your normal routine to distract yourself from the rejection. How do you say you’re too busy when there’s no place to go? We hear different stories of relationships being impacted by ghosting during the pandemic, including one where a company decides to ghost a single when he needs his job the most. And how does becoming newly unemployed affect your love life? Also, we’ll hear back from two of our singles from Episode 1 on how their relationship status has evolved.


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Apr 29, 2020
Ground Rules

Our hosts, Andrea and Ben, are observing self-quarantine through different lenses. Andrea is in the dating world and understands how difficult spending days alone can be while Ben is married and quarantined with his wife. We’ll meet three singles who are dealing with different relationship issues in this “stay at home” environment. From gauging the interest of two potential suitors, to weighing the dangers of casual sex, our hosts will discuss and debate our participants’ decisions.

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Apr 22, 2020
Introducing Dating Diaries: Quarantine Confessions

New episodes of Dating Diaries: Quarantine Confessions will air every Wednesday starting April 22, 2020!

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Apr 16, 2020