We made out in the hot tup, and then… (a Juneteenth recap)

I’ve talked at length about those who I have dated. There was Joe, my would-be husband had things not ended terribly and appropriately. Then John, the flight attendant I tried to date. But before either of them was Tim, again, not his name, but you see the pattern. We reconnected at Juneteenth celebration in Dallas. Now I’m all fucked up in the heart.

Tim & Juneteenth

Long ago, Tim was a guy outside of my norm. Where I usually like dark skin, he was not. And where I usually liked slight, tight bodied bottoms, he was neither of those things. Tim was educated and ambitious, dedicated and caring. He was a healthy evolution when everything in my ego wanted to remain the same.

He and I dated briefly but remained friends–social media friends at least. Our lives took us to so many places, each farther away than the last. Then, one Juneteenth weekend, we finally got into each other’s space to say what needed to be said.

I am Jai The Gentleman and this Dear Black Gay Men Podcast. It’s a short, bullshit-free step out of our comfort zone to talk about all the emotional ups-and-downs along the journey to happiness. Hopefully, this is our weekly reminder of how dope it is to be Black gay men who love Black gay men. 


Dating someone accomplished has been difficult for me. At first, it was my save-a-hoe complex. If a suitor didn’t present enough problems that my ego convinced me only I could solve, I lost interest. Thank Oshun that my therapist healed that brokenness. Then my deeply African upbringing told me that I need to be the provider in my house. Again, thank Oya that I realized it won’t be my house. When I get married, it will be our house that we build and enjoy equally.

Whether it was therapy or personal evolution, I had to realize many of my flaws that were on full display when Tim and I dated. And that is why our meeting at Juneteenth was so monumental.

A Lesson on Ego

Tim may have been the best person I’ve ever dated. He required me to be better without forcing me to be anything but myself. He heard me and held me in ways that I couldn’t appreciate until after I fucked it up. Parts of me–the majority of me–knew this while we dated. I knew he was what my life needed, but my ego wouldn’t let me settle into him. My insecurities told me that the life he deserved was not one I could provide for him. So I sabotaged it, and probably hurt him in the process.

Despite all my shortcomings though, he still held a flame for me. We necked in his hot tub after, for the first time, I was able to express to him. And, true to form, he heard me, and saw me. I wondered why had I been so fucked up while being equally thankful that I’m not fucked up anymore.

You probably read this hoping for the salacious details of our tongue acrobatics. But really, this is my love letter to Tim. I hope he knows who he is.

Thanks Tim for being absolutely yourself, especially when I couldn’t be mine.

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