389: Sydney Castillo on Losing His Brother, Mother & Facing Death | The HoneyDew with Ryan Sickler #389

The HoneyDew with Ryan Sickler

Ryan Sickler

Comedy Interviews, Comedy, Stand-up

4.9 • 9.9K Ratings

🗓️ 8 June 2026

⏱️ 70 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

SPONSORS QUO -Make this the season where no opportunity — and no customer — slips away. Try QUO for free PLUS get 20% off your first 6 months when you go to QUO.com/honeydew HIMS -Ready to reach your goals? Visit hims.com/honeydew to get a personalized, affordable plan that gets you. ProtonVPN -Right now, Proton VPN is offering our listeners 70% off a two year plan when you go to ProtonVPN.com/HONEYDEW My HoneyDew this week is comedian Sydney Castillo! Sydney Highlights the Lowlights of losing his brother to a stroke and his mother to cancer just one year later. We discuss growing up with an older father and the perspective it gave him on life. Sydney also opens up about navigating grief, family conflict, and discovering that a cousin had been stealing money from his mother’s account as her memory began to fade. It’s a powerful conversation about loss, family, mortality, and learning how to cope with death. Check out Sydney on the road at a show near you! 🎟️See me live. All tickets at www.ryansickler.com/tour 🎤Check out my new standup special “Live & Alive” streaming on my YouTube now! http://youtu.be/PMGWVyM2NJo?si=SrhXjgzR1pe6CyYE 👉 Subscribe for more standup and new episodes of The HoneyDew, The Wayback, and more! http://youtube.com/@rsickler ✅ Subscribe to my Patreon “The HoneyDew with Y’all”! Get The HoneyDew audio and video a day early, ad-free, for just $5/month! Want more? Upgrade to the $8/month premium tier and get everything above plus The Wayback a day early, ad-free, censor-free, and exclusive bonus content you won’t find anywhere else! http://patreon.com/RyanSickler 📧What’s your story?? Submit at honeydewpodcast@gmail.com 👕Get Your Merch👕 http://www.bonfire.com/store/ryansickler/ 🎧 Listen to my Podcasts 🎧 The HoneyDew - http://podcasts.apple.com/us/podcast/the-honeydew-with-ryan-sickler/id527446250 The Wayback - http://podcasts.apple.com/us/podcast/the-wayback-with-ryan-sickler/id1721601479 Patreon - http://www.patreon.com/ryansickler 📣 Follow Me📣 ▪ Instagram: http://www.instagram.com/ryansickler/ ▪ TikTok: http://www.tiktok.com/@ryan.sickler ▪ Facebook: http://www.facebook.com/RyanSicklerOfficial 🕸️ryansickler.com/ 🍈thehoneydewpodcast.com/ 🦀Subscribe to The CrabFeast Podcast🦀 http://podcasts.apple.com/us/podcast/the-crabfeast-with-ryan-sickler-and-jay-larson/id1452403187 Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	The internet is coaching our kids.
0:04.0	When boys hear that on repeat, it shapes how they see themselves.
0:08.0	We can't leave it to those voices.
0:10.0	We have to be louder.
0:12.0	Together with EEE, we need to coach them, guide them, back them.
0:15.0	Building our boys up every chance we get.
0:18.0	Be yourself. Back your mates.
0:20.0	Confidence comes from a vin. As proud partner proud partner of the England team's EE has support and guidance to help build all our voice up on and off the pitch. Search EEE Yes, Boys. Indeed presents. Hires, you can't afford to get wrong. Like payroll manager. Hi, I was just checking my pay slip and it's all in Japanese yen. Yes, you're welcome. Sorry? Given the exchange rate between the pound and the yen, you're technically a millionaire now. Don't spend it all in one place. I can't really spend it anywhere. This is a job for sponsored jobs. This is what happens when you don't sponsor your job on Indeed. So the next time you need someone to get the job done right, get matched with quality candidates with an Indeed sponsored job.
0:56.8	Visit Indeed.com slash next hire and sponsor your job today.
1:00.2	Tulsa, Oklahoma.
1:01.4	I'll be there Friday, June 19th and Saturday, June 20th.
1:05.6	All tickets on my website at Ryan Sickler.com.
1:14.1	The Honeydew with Ryan Sickler Welcome back to the honeydew y'all. We're over here doing it in the NightPants Studios. I'm Ryan
1:30.5	Sickler, Ryan Sickler.com and Ryan Sickler on all your social media. I want to start by saying thank you guys for supporting this show or for supporting anything I do. And if you've got to have more, go get the Patreon. It's five bucks a month and it is this show with y'all, the honeydew with y'all. And I promise you, I've said it forever, you won't find crazier stories on the internet. All right. If you or someone you know that has a story that needs to be heard, submit it to Honeydew Podcast at gmail.com.
2:02.7	If you sent it before, send it again. Bump it to the top. We get a lot of them. We would love to do your story. All right? That's the biz. You know what we do here. We highlight the low lights. I always say that these are the stories behind the storytellers. I am very excited to have this guest with us. first time on the honeydew.
2:17.4	Ladies and gentlemen,
2:18.4	Sidney Castillo.
2:19.4	Welcome to the Honeydews.
2:20.7	I appreciate you having I am very excited to have this guest with us. First time on the honeydew. Ladies and gentlemen,
2:18.4	Sydney Castillo,
2:19.3	welcome to the honeydew city. I appreciate you having me, man. Thank you for being here. You guys set up, man. Thank you very, very much. Before we get into what we're going to talk about, right there, promote everything and anything you like. Let's get it. Hey, listen, I'm all things Sydney is funny.
2:33.0	S-Y-D-N-E-Y is funny.
	...

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