Gay Men Going Deeper
Gay Men Going Deeper
Michael DiIorio & Matt Landsiedel | Gay Men’s Brotherhood
Liked by Everyone, Chosen by No One: The Nice Guy Trap
49 minutes Posted Jul 9, 2026 at 10:00 am.
Gay Men Going Deeper: The Nice Guy Trap
Being Nice
What Does Being A Nice Guy Actually Mean To You?
Matt on Being A Nice Guy
Have You Ever Been The Nice Guy?
Is Your Friend Think You're A Nice Guy?
What Is Niceness In Your Relationships?
Gayman's Brotherhood: Connection Circles
Why Being a Nice Guy Backfires in Dating
Matt Says Being Honest In Dating Backfires
In the Elevator With Michael
Gay Men on Dating and Relationships
How to Shift From Being Nice to Being Chosen
How To Be With Yourself
Be Candid With Yourself
Michael Jackson on Not Being Like Everyone
Matt on Not Being the Nice Guy
Thank You!
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Show notes
A lot of gay men pride themselves on being “nice”— easygoing, agreeable, low-drama. But what if that’s exactly why you’re not getting what you want?
In this episode, we break down the difference between being kind and being “nice,” and how approval-seeking, conflict avoidance, and over-accommodating are quietly killing attraction, respect, and real connection. 
We talk about:
Why “nice” is often a strategy, not a personality
The hidden cost of being liked by everyone
How this shows up in dating and relationships
The difference between being chosen vs. being liked
How to shift from approval-seeking to self-respecting
If you’ve ever felt overlooked, under-appreciated, or stuck in the friend-zone, this one will hit.
Today's Hosts:
Matt Landsiedel
Michael DiIorio - Take the 360° Self-Review for Gay Men
Reno Johnston
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