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That's 30 years older than Jayden was when he and I met four years ago in Melbourne on a night when he was out with his soon-to-be ex-girlfriend.

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That's how young he was: He hadn't yet come to terms with his sexuality, never mind coming out of the closet. As he later told me after ardently pursuing me, our meeting provided his moment of clarity. Meanwhile, I knew he was all wrong for me. He was still in university and dependent enough on his parents to be terrified to tell them that he was gay. Despite the social and economic limitations of his youth, I was attracted to his openness and his fearlessness if coming out wasn't the dare involved. I was his first boyfriend, and he dived right into the relationship, unencumbered by the baggage of past loves and disappointments.

He may have looked like a baby, but the courage and vigor with which he pursued me was all true man. As with most of my relationships with younger guys, none of which were just about sex or my paying their way, we had a smooth ride out of the starting gate because there weren't all those roadblocks that get bumpier as potential mates get older: He hadn't lived long enough to compile a lengthy list of rules, so he forged recklessly ahead.

Sadly, that old devil called doubt, with insecurity as its pitchfork, would eventually come between Jayden and me. Several months into our romance, he told me about a dream he had in which I left him for someone closer to my own age, a grown-up with a career and a home who was out and proud. I may not have known what was best for me, but Jayden thought he did. I knew the end was coming, though it didn't arrive for another six months.

People from different generations can grow even farther apart. But if I learned anything while sorting through the wreckage of our relationship once it was over, it wasn't that guys half my age are too young for me. I couldn't imagine getting involved with anyone else who wasn't completely out of the closet, but I wasn't ruling out a future boyfriend who was born after the Class of '87 graduated from high school.

I don't believe a twentysomething is inherently worse for me than a man in his forties. I've dated enough of my contemporaries to know that they're not necessarily more mature or well adjusted. Stevie Wonder, Kate Bush and The Beatles created some of the most enduring music in the history of rock and roll well before they turned 25, so youth does not necessarily equal undeveloped.

And being older certainly doesn't mean you have your shit together. It's not like I lived happily ever after with any of the people my own age whom I dated before I turned It's not like any of those relationships were easier -- or better.

What Grindr Taught Me About Dating Older Men

I hate that guys born after the Reagan Administration rarely have the same points of pop-culture reference cases in point: His life was set the fuck up. His ceilings must have been 30 feet high, and his parties had bartenders. That day was very nice. He indulged me by following Laura Dern around instead of looking at the gardens, which was definitely not the first time she had been stalked by gay men at a garden party.


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Afterward, we had wine with some of his straight friends. By the end of the day I had done something uncharacteristic for me at that time: I asked him about his life instead of talking about mine. What were the hardest years? When did he get real?

Ep 6 Clip: Dating & The Gay Age Gap

When did he make money? Twenty years after becoming successful, what did it feel like now? I gathered my information, came, and then went home to my basement. We maybe hung out romantically once more after that, but then it faded in a natural way. This kind of thing happened a couple dozen more times in my early 20s.

Ten Reasons Younger Adult Gay Men Like Older Adult Gay Men | Jimbolaya

A huge theme in all my work is confidence. From the moment you realize as a gay man who you are, whether it's a challenging process or not, you know maybe subconsciously that a lot of the world hates you. Some want you dead.


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  8. I knew it was harder for me to get what I wanted, and a lot of that was self-inflicted. I didn't think I deserved what I knew I wanted. What I was doing in my early 20s, by dating older men, was showing myself that maybe there was hope.

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    That someday I could make some money and be successful and create a life for myself, just like these older men. It was a genuine sense of confidence from the inside. Most gay men never reach the end of this process, and many never start.