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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 - Take the 360° Self-Review for Gay Men
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Matt Landsiedel
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- 0:05Gamin Going Deeper: Being Single & Ready To Mingle
- 1:46What Is Single and Ready To Mingle?
- 2:27What Do You Love About Being Single?
- 5:02Mixed Messages on Dating and Singling
- 6:02What's Your Favorite Stage Of A Relationship? The Honeymoon Phase
- 10:22Matt on Conflicts In His Relationships
- 12:06Single People Talk About The Best Things About Being Single
- 16:13What I Need In A Good Relationship
- 17:50What's The Non-Negotiable Item In A Relationship?
- 20:43Gay Men's Brotherhood
- 21:22When Are You Ready to Mingle?
- 24:31Gay Men on Matching Apps
- 28:26"Does It Mean I Attract a Polyamorous Partner?"
- 31:49Are You Dating Gay People?
- 33:28Gaiman's Going Deep: Relationships and Dating
- 34:25What Would You Like To Experience The This Time Around?
- 39:17What You Need To Know About Chasing
- 43:10What I Want In A Relationship
- 43:52Matt on His Sexual Life
- 46:14I Should've Knew That My Best Friend Had Sex With Her
- 49:28"That's Off-limits" For Gay People
- 49:47Gay Men's Brotherhood: Connection Circle