Stepping out onto the dating scene after ending a long-term relationship can be a challenge. Coming out onto the gay male dating scene after living as a straight man–and a married one at that–is an incredible feat. First of all, the rules of dating you learned as a straight man? Throw those out the window. It’s a whole new ball game fellas, with a brand new set of rules–or lack thereof. A relative newbie, I won’t pretend to know, let alone understand, any of these apparently mailable rules. In fact, if you have any pointers, please, comment away. I could use a clue…or twenty.

My very first date with a man was during the short-lived “open marriage” period that preceded my divorce. First of all, he went for a questioning married guy. RED FLAG. Married, to a woman, dad to twins, exploring openness and bisexuality? I wouldn’t have touched me with a ten a foot pole! He was nice enough, but “nice” is of course that empty descriptive device we use–the one that offers absolutely nothing useful about a person’s character. I didn’t manage to learn much about Nice Guy that night. He was tentative and I was distracted by the fear and excitement of putting myself out there–years of silent wonder finally boiling over into action. But, for all I knew that night, ours was the epitome of a gay date: a coy struggle to find out as much as you can while offering as little as possible. (My straight friends lament how there’s nothing gay about it; that’s just dating. Perhaps I had forgotten.)

It started the way all great romances of the internet age do, with a wink or a poke that demands zero effort and involves even less risk. Yet, I was downright giddy about the playful text messages, which became “let’s see” cocktails, followed by a “this could be interesting” dinner, and then an “ok, so you seem normal” after-dinner drink. When he invited me up to his apartment, which was “on the way to my train,” I was too naive to recognize what it was really about for him, and too overwhelmed to understand what it meant for me. To be clear, the excitement I felt had nothing to do with Nice Guy. What I knew of him could barely fill a thimble. What I was really excited about was the truth of my sexuality completing its 30+ year journey to the surface.

I sat there on his couch. He fumbled with the radio. Top 40s. (Eek.) I tried to strike up a conversation to drown out the awkwardness, something about a new band I had just discovered. “My friends hate this about me,” he starts, “I don’t really like music.” (I love music.) “I mean, I like to hear it, but there’s nothing that I feel that strongly about.” (I feel strongly about your musical ambivalence.) I shifted the conversation, playfully commenting on how every one of his profile pics captured him in plaid. He proceeded to show me his closet. (Yes, really.) It was almost all plaid. Hipster plaid. Maybe he was just as nervous as me.

Back on the couch with Katy Perry, he asks “so, what kind of guys are you in to?,” tracing the back of my hand with his index finger. (No, not nervous.) Someone who is self-aware, emotionally available, takes more risks with his heart than anything else . . . I said none of these things, and turned the question back to him. “Well, I’ve never been out with a guy wearing one these before,” he says, rubbing my finger–the one with the wedding band. Was I supposed to take it off? I didn’t know. I didn’t even think about it anymore. He clearly was, and it was working for him.

I hadn’t had a first date in 7 years. But I was not so out of practice that I didn’t know what “do you want come upstairs?” meant. Indeed, I had many a date with a young lady that ended with a cup of coffee up in her kitchen or an episode of Gilmore Girls on her couch. But now his mouth was on mine, and two strong hands slid up my back. His lips touched my neck and the gentle scrape of his stubble made me shudder. He began to unbutton my shirt. Layers dropped on the floor as the skin of our chests met. He touched my belt. “This might be too much.” I hated saying it. I wanted this experience. I wanted to know how it felt to be with a man. More than a drunken college hookup, where I wasn’t just fumbling around next to a boy and pretending it wasn’t happening.

“Do you at least want to get off together?” he asks, pulling down his pants. (At least the boxers weren’t plaid.) Before I could answer, he was at it. We kissed while he finished. My pants stayed on. Afterward, he comments on how great it is to be gay because you could find sex anywhere, anytime you wanted. “I guess it has its benefits,” I fake-laughed. I tried to explain that I wasn’t just looking for sex. Of course, I’m interested in the physicality of it all, I explained–but I want to experience what it’s like to be intimately and emotionally connected to a man. As he saw me out the door, I got the sense that my wedding band wouldn’t be the only thing keeping me from experiencing that connection.

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gayDate: A Story of Firsts

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