Season 2 E:09 "Online Date Leads to Bender"

What this episode covers

In this episode of Don't Be Sorry Be Better, Dicky Braggs recounts to Theo and Ronnell what might go down as one of the worst (or best, depending on perspective) dates of all time. What started as a simple online match quickly spiraled into a disastrous evening—awkward conversations, unexpected guests, and a bill that made Dicky question his life choices. But the real story begins after the date, as Dicky embarks on a legendary four-day bender featuring a rotating cast of strangers, VIP champagne rooms, and some truly questionable decisions. Can Theo and Ronnell piece together what actually happened? And more importantly—did Dicky ever make it home? Tune in for wild storytelling, regret-filled laughter

Share this episode

Similar Episodes

183. Yuta Katsuyama: Folding Culture Into Every Rice Ball

Apr 22, 2026 ·87m

182. Charles Wong on BBQ, Culture & What Comes Next

Apr 14, 2026 ·104m

181. You Don't Need a Crisis to Ask for Help — Holley Brandchaft-White, SHFT Behavioral Health

Apr 8, 2026 ·177m

180. A Love Letter To Pizza in Chicago ft. Tony Scardino [Professor Pizza]

Mar 25, 2026 ·95m

179. Immigration Law ft. Anastasiia Bilousko, ESQ and Mia Isberto

Mar 17, 2026 ·83m

178. Da Local Boy ft. Nate and Dianne

Mar 10, 2026 ·88m

Similar Podcasts

The Sacred +Profane Podcast nephtaragrace The Sacred + Profane Podcast is a provocative conversation dedicated to cementing a better future for all. We specialize in unpacking the nuances of what is considered sacred and profane, particularly focusing on sex, death, and all that pertains to the circle of life. Our aim in focusing on such ”taboo” subject matter is to demystify what is unconscious, bring to light what has been known for centuries as ”the occult,” and empower the rapid transformation that is occurring on the Planet. Explicit Creativity Threads Life w/ Mr Benja Mr Benja Welcome creatives! These are discussions, thoughts, case studies, interviews, and lessons about how our creativity relates to life. The host, Mr Benja, is a former video game programmer / designer for Rockstar Games, Sony Santa Monica, The 3DO Company, and others, as well as a fine artist. -- Be sure to check out the website for more. Explicit The Commonality Podcast with Pilar Pilar Lyutfalieva The Commonality Podcast explores what it means to do our best in today’s messy beautiful world. Hosted by Pilar, a personal and professional coach, we dive into it all with a mix of honesty, humor, and heart. Whether it’s solo musings, breaking down weird astro sh*t, or listening to guest stories, this is your space to remember this life is non linear and you're not alone. Explicit I am Consciously Curious Victor Chan I am Consciously Curious is a Chicago based podcast that dissects passionate individuals in various industries. The goal is to share their stories to inspire you to cultivate meaning within your own space. If you are interested in coming on or know someone that would be great for the podcast, please message us on fb/ig: @iamconsciouslycurious Explicit

Frequently Asked Questions

How long is this episode of Don't Be Sorry Be Better?

This episode is 1 hour and 4 minutes long.

When was this Don't Be Sorry Be Better episode published?

This episode was published on April 1, 2025.

What is this episode about?

In this episode of Don't Be Sorry Be Better, Dicky Braggs recounts to Theo and Ronnell what might go down as one of the worst (or best, depending on perspective) dates of all time. What started as a simple online match quickly spiraled into a...

Can I download this Don't Be Sorry Be Better episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.