Jack: “Does everyone here think you’re straight?

Kyle: “Yeah. And I am. Little curious though.

Jack: “Ohhh haha ok 😉

Kyle: “Haha, but you’re a good looking guy

Jack: “Ha well thx. You too

Kyle: “You should come over

The above is the first conversation I ever had with “Jack”. I had just given him my phone number and we were on a yacht, playing footsie, at sunset. Cute, right?

Hours before, I just unwittingly unhinged myself from a semi-dependent friendship – or rather, a complicated relationship with another person – because of an article I had written on this very blog that completely outraged him into never wanting to speak to me again. He was done; tired of being hurt by me, a person that would never reciprocate the same feelings toward him. And also probably hurt by the fact that I admitted I wanted to date girls again. I was upset by his reaction, primarily because there was someone alive in the world that had such contempt for me. But all the uncertainty of losing an integral person in my life completely fell overboard the second I laid eyes upon Jack. It was like-at-first-sight.

Piercing eyes, devastatingly handsome, with ever the slightest twinge of mystery, Jack captivated me in a way that was completely new and unexpected. He came on board the yacht of our mutual friend with his roommate, Sam, who was completely the antithesis of him. For every, calm, cool, and collected nerve inside of Jack, there was a bombastic, hilarious, and brazen comment that spilled out of Sam that left me in stitches. He even stood at the helm of the yacht and mooned all of us within an hour of my meeting him.

When we were anchored at sea, drinking and watching the sunset, Jack and I were leaning with our backs to two walls directly across from one another. I slipped my foot in between his before commanding the courage to ask for his number, which he promptly gave me and sent me the above text. Truth be told, I had just come off a string of dating three girls, none of whom I felt any special connection with (Spoiler Alert*** I was gay). Jack made me call into question my most recent dating choices; was I really into guys? Or was it just him?

When we docked, Jack had to drive a now-drunken, but still hilarious, Sam, back to their home in Hollywood, while I was headed back to my house in Long Beach. Needless to say, my invitation to come home with me never quite panned out. I said goodbye to my new acquaintances feeling excited, smiling to myself. I couldn’t help but think the old saying was true; “when one door closes, another one opens.” I had abruptly ended a significant chapter of my life, and on the same day, I was confident that a completely new one would be starting.

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Founder & Creator of Hamptons to Hollywood, lifestyle blogger, entertainer, and all-around lover of life.

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