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Dating Diaries: Questions and Confessions

Entered in Podcast


In 2020, our initial season was focused on dating in Covid. Since then, Dating Diaries: Questions and Confessions has become one of the most popular podcasts in the modern love category, covering all things dating advice, relationships and the methods in which people connect in this digital age.

The series has evolved into a podcast that addresses the challenges singles and couples face every day.  Our audience spans from college students to adults rediscovering their romantic and sexual selves later in life.

We have sought to be more proactive in searching out singles who have shared their stories on social media platforms. We also get DMs and emails from fans of the show asking for help. We love inviting them to share their story on the podcast.

Strategy and Execution

With Dating Diaries, we wanted to offer dating stories that are emblematic of modern dating through the lens of two longtime best friends with great chemistry. These stories are sometimes uplifting and other times heartbreaking.

For example, we meet an actor who feared he gave his partner gonorrhea only to find out his partner gave him Covid. We heard another story about an adventuresome young woman who is certain she slept with an alien after a nearby UFO sighting. And we hear from a single father who asked for help with his online dating profile after receiving no swipes in a year. Andrea Gunning and Ben Fetterman unpack the complexities and experiences of humans just trying to find their person. 

The advice and feedback our hosts offer is candid, funny, and practical. And while the hosts focus on one single person at a time, the messages are always applicable to a larger community of people looking for love and companionship.

What started as an outlet for singles to vent about the perils of dating during a pandemic, Dating Diaries: Questions and Confessions is the podcast that is exploring dating culture, intimacy and love in our new normal. The show tackles all the uncertainty singles have about how to approach love, vulnerability and intimacy.


Listener engagement on Dating Diaries is exceptional. Email letters to hosts are lengthy, personal and often reference specific stories or moments on the podcast. Reviews emphatically support the show. DMs on the show’s Instagram account often include the show’s lexicon of the host’s expressions including terms like, “step-over text”, “rock climber” and the dreaded “molotov cocktail text.”

The podcast has been featured by outlets such as People Magazine, Forbes, Elle, Cosmopolitan and many others  for its entertainment value and dating advice. Our past accolades include being featured on Apple’s Flowcase and covered on Access Hollywood and ABC, NBC and CBS news affiliates.


Video for Dating Diaries: Questions and Confessions

Entrant Company / Organization Name

Glass Podcasts


Entry Credits