Dear Black Gay Men’s Substack

Dear Black Gay Men’s Substack

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Dear Black Gay Men’s Substack
Dear Black Gay Men’s Substack
I'm Miserable Without Him
The 40-Something Swipe Right

I'm Miserable Without Him

Have You Ever Wanted Your Ex Back? It's Okay I Do, Too

Jai The Gentleman's avatar
Jai The Gentleman
Apr 11, 2025
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Dear Black Gay Men’s Substack
Dear Black Gay Men’s Substack
I'm Miserable Without Him
2
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By Any Means Necessary

I stood on that corner pleading my heart out for this man. I wanted to him to relent his position and see me. I honestly believe I would have gotten on my knees if I thought it would have changed anything.

Kevin and I had had our ups-and-downs along the journey of dating.

He helped me uncover some unknown insecurities that, of course, I’d never addressed. But as with any content creator, I’d imagine, I process everything out loud…sometimes in front of mics and cameras.


The 40-Something Swipe Right

This Break-Up Broke Me. Have You Ever Been There?

Jai The Gentleman
·
Mar 27
This Break-Up Broke Me. Have You Ever Been There?

God, Please Help Him Reconsider

Read full story

I wanted to work through my issues with him. I wanted him to hear that I’m working. In the end, I just wanted to reassure him that I got it together and I’ll try even harder next time. But none of that worked.

In me, there was this nagging feeling that if he walked away from me, my life would implode. He was the pillars holding up my otherwise fragile existence. Even as I type that, I know it sounds crazy and unhealthy, but that’s what I thought when break-up was looming.


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At that moment—in that short conversation where I fought for my man—I didn’t see a life without him.

Looking back, though, I don’t want to have seen life without him. I knew that dating him would change the trajectory of everything I was doing. My business, new businesses, my podcast, my relationships with my family would all have been enriched with Kevin by my side.

What I was fighting for was that future. The future that was plotted clear as day with him hand-in-hand. I loved the me I was with him and on that afternoon, I didn’t know if I could be that same me without him. Then I realized.


On New Terms

What came the days later was a new awareness.

After my last big break up, I’d called Maquan. Joe (my ex before Kevin) and I had lived together. One day, ironically the day I’d planned to buy his engagement ring, Joe came home and told me that he’d rather move on alone.

Over the next couple hours, I found myself sleeping on an air mattress in the apartment that I paid for watching Black Is King on my iPhone. My life felt dismal so I called my only comforter at the time and told him my problems.

Maquan listened for a minute, asked questions where appropriate, and waited for me to get all my commiserating out before he said one thing that has stuck with me ever since.

I said, after 2 years of planning my life with Joe, “Who am I without him?”

Maquan replied, “You’re Jai motha-fucking Makokha”.

That’s all I needed to snap out of it. I finished streaming Beyonce’s African opus, logged on to Zillow and was out of that apartment that I’d paid for by the next morning.

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