Certified life & wellness coach. Helping you build authentic self-confidence from the inside out. I don’t use Facebook DMs. Start at wellismo.com
Michael DiIorio is a certified life & wellness coach, Founder of Wellismo Coaching, leader of Gay Men’s Brotherhood, and co-host of the Gay Men Going Deeper podcast. Michael uses a collaborative approach to coaching that is solution-focused and action-oriented. He specializes in confidence, sexuality, and relationships.
22/05/2026
If you like out-of-the-box journal prompts and future self work, read this:
Better Questions Build Better Lives | Gay Life Coach Stop fantasizing and start building. A gay life coach in Toronto shares 3 better questions to design a clear, intentional life vision that fits you.
Dating intentionally doesn’t mean killing the fun.
It means knowing whether you’re choosing someone because there’s real interest… or because being alone feels uncomfortable.
From Gay Men Going Deeper Podcast Ep. 272: Single and Ready to Mingle.
You expected hate from straight people.
You didn’t expect it from your own community.
But a lot of the time it’s not about you.
It’s what you represent:
Confidence.
Freedom.
Unapologetic expression.
That hurts people who haven’t allowed themselves to go there yet.
So they judge it and attempt to tear you down.
Have you seen this dynamic play out?
12/04/2026
Sure, you can change your mind about just about anything. But sometimes it's easier to just let go completely. This looks at the cost of being overly "determined" in your healing journey:
When the Mindset Work Isn’t Worth it - Wellismo | Life Coaching for Gay Men I often remind my clients that the people in our lives are not good or bad; they’re neutral. It’s only when we start having opinions about them that we put – Personalized support for gay men seeking confidence, clarity, and purpose.
Gay men grow up wanting approval and acceptance from straight men.
But in adult life…
A lot of straight men are quietly looking at gay men thinking:
“How are they so free?”
Free to express themselves as they see fit without playing by the same rigid rules around masculinity.
No, it’s not perfect in the gay world.
But it does make you wonder:
Are we chasing something they have…
while they’re craving something we’ve already built?
What do you think:
Who actually has more freedom? Gay men or straight men?
If you grew up in a world where being gay was stigmatized, it’s nearly impossible not to have some remnants of internalized homophobia lingering.
This isn’t a personal failure.
It’s something you learned.
The work isn’t to shame it…it’s to notice it.
🎙️ We unpack this in Episode 284 of Gay Men Going Deeper: “Masc 4 Masc: Preference or Internalized Homophobia?”
The inability to follow through isn’t just annoying. Look closer. If you’re inconsistent with others,
you’re probably inconsistent with yourself too.
That project you keep restarting.
That routine you never stick to.
Those goals that quietly disappear.
It’s the same pattern.
This isn’t about your calendar.
It’s about fear, avoidance, and a lack of self trust.
Save this. Or send it to your flakiest friend.
In my 40s, I don’t date like I used to.
For a long time, I thought I was being “easygoing.”
Low maintenance. Chill.
What I was actually doing was tolerating things that I genuinely don’t like.
Inconsistency.
Confusion.
Potential with no follow-through.
But patterns don’t lie.
At some point, you stop trying to make it make sense…
and you just opt out from what doesn’t meet your standards.
This isn’t being picky. It’s paying attention to what actually works for you - and not settling for less.
If you’ve dated in the gay world for more than 5 minutes, you’ve met the “maybe” guy:
Vague plans. Soft interest. Just enough attention to keep you around.
Clarity is attractive. Ambiguity is avoidance.
We go deep on this in this week’s podcast episode about flakey g**s. It’s out now on Apple Podcasts. Available on all platforms on Thursday
Somewhere along the way, we started equating social media metrics with confidence.
That more followers = more confident and likes = more secure.
But confidence isn’t measured by applause. It’s measured by how you show up when there isn’t any.
The loudest profiles aren’t always the most self-assured… and the most self-assured men often aren’t trying to prove anything at all.