Description

In this episode, Michael and Matt get personal about what we love about being single, how we knew we were ready to start dating again, and what we want to experience differently this time around. We talk about flirting on apps, dating in 2026, and all the messy, exciting parts of putting yourself back out there when you’re ready to mingle. 

Some of the topics we cover in this episode are:

• Getting back into the dating world

• When your nervous system tries to hijack your dating life

• Red flags and green flags

• What we’re actually looking for in a man now (and how that has changed) 

It’s cheeky, honest, and surprisingly insightful. If you’re single (or single-ish), you’ll feel right at home.

Today's Hosts:

• Matt Landsiedel
• Michael DiIorio
• 360° Self-Review for the New Year

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• Watch podcast episodes on YouTube
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- LEARN WITH US -

• Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others.
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• Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series.
• Take the Attachment Style Quiz to determine your attachment style and get a free report.

Chapters

• (00:00:05) - Gamin Going Deeper: Being Single & Ready To Mingle
• (00:01:46) - What Is Single and Ready To Mingle?
• (00:02:27) - What Do You Love About Being Single?
• (00:05:02) - Mixed Messages on Dating and Singling
• (00:06:02) - What's Your Favorite Stage Of A Relationship? The Honeymoon Phase
• (00:10:22) - Matt on Conflicts In His Relationships
• (00:12:06) - Single People Talk About The Best Things About Being Single
• (00:16:13) - What I Need In A Good Relationship
• (00:17:50) - What's The Non-Negotiable Item In A Relationship?
• (00:20:43) - Gay Men's Brotherhood
• (00:21:22) - When Are You Ready to Mingle?
• (00:24:31) - Gay Men on Matching Apps
• (00:28:26) - "Does It Mean I Attract a Polyamorous Partner?"
• (00:31:49) - Are You Dating Gay People?
• (00:33:28) - Gaiman's Going Deep: Relationships and Dating
• (00:34:25) - What Would You Like To Experience The This Time Around?
• (00:39:17) - What You Need To Know About Chasing
• (00:43:10) - What I Want In A Relationship
• (00:43:52) - Matt on His Sexual Life
• (00:46:14) - I Should've Knew That My Best Friend Had Sex With Her
• (00:49:28) - "That's Off-limits" For Gay People
• (00:49:47) - Gay Men's Brotherhood: Connection Circle