On a frustratingly cold and grey early summer day, my best friend and I were walking back to his office, drinking our Jamba Juices after lunch at Max Brenner’s in Union Square. We never need an excuse to have a workday lunch together, but I had specifically called this meeting. The topic: “What’s up with Ken’s love life?” It’s not something I typically ponder, which is probably why there hasn’t been much going on in that department. I needed John’s always-sage advice.
Truth is, my life is organized the way I like it and I haven’t really lamented being single too much. In fact, by and large, I’ve embraced it. But lately—blame age, horniness, being surrounded by people in long-term relationships—I’ve started to eye my prospects for love and dating again. And to consider if that’s what I really want.
It’s been four years since my last real relationship and the man-break was necessary, to put it kindly. The previous six years had been a heart-wrenching back and forth with someone I loved very much but who was never a good match for me, nor I him. It made me fundamentally doubt my desire—and capacity—for a long term relationship.
However, living in New York—the place with probably the highest number of gay men in the world—has been a constant reminder of what I’m missing.
The problem for me has always been how to go about it. Historically, I’ve done one of two things: held people at a full arm’s length, or fallen in love immediately. Casual dating is like Sanskrit to me. I honestly don’t know if I’m wired for it. As an analytical person, I tend to sum up a potential mate immediately and make an almost instantaneous binary yes/no decision. John noted this as he dispensed his advice.
“This summer you shouldn’t worry about getting involved with anyone,” he said. “You should just spend the summer dating. Have some fun. Meet lots of people—and lots of types so you see what’s really out there.”
That was the carrot. Next came the stick.
“You get involved in situations that are beneath you,” he cautioned, meeting my gaze. He wasn’t only referring to the negotiated nature of most of my relationships, but also my tendency to find broken people who need a hand. It comes from a good place, but serves me poorly.
Only a best friend can get away with such a bold “observation.” But as harsh as it sounded, it came from love and was even a compliment in a weird way. I knew it was designed to stun my insecurities into submission, and it worked because I know two key things about John: 1) such dynamic proclamations from him are rare and therefore meaningful; and 2) he’s almost never wrong.
He was right as he implied—gently and with consummate therapist-like sensitivity— something I already knew. I choose people because I know it won’t work with them. According to my collective, unofficial life coaching team of John, my sister Sandi and my old therapist from Orlando, I do this so that I can have some viable emotional connection while still sidestepping actual commitment.
I can’t blame the boys—and truth be told they all had certain boyish qualities, even when confined to a simple lack of maturity. If you feed the lions at the zoo despite signs advising against it, it’s not the lion’s fault when he gets confused and eats you.
I have received rewards for my ambivalence. I could be the daddy without having to make any promises. I could feel connected without someone cluttering up my apartment. I could have all the guiltless sex I want. As a result, inappropriate and/or unavailable have been my stock and trade since I came out.
But this hasn’t insulated me from heartbreak. Intellectually I choose men because they’re unavailable, but my heart doesn’t distinguish the difference. Because I’m not made of stone I end up having feelings, and those feelings have gotten hurt.
John offered a new perspective. If you’re going to get your feelings hurt anyway, why not go for it and do it for the right reason? Let attraction develop. Let lust progress into something more meaningful. And then if things go south, at least you won’t have any regrets.
It seems a simple lesson, particularly for a 43-year-old man. Accepting that you’re not good at everything is not the worst object lesson for someone like me. I have my talents, but I exhibit bad judgment when it comes to men, and I have astonishingly poor directional sense. It’s my unique birthmark.
The logistics of the ‘Summer of Dating’ are simple: (1) go on at least one date a week (repeats don’t count); (2) tricks don’t count (Don’t give me that look—you know the difference) and should be limited; (3) hold off on any sort of commitment until Labor Day; and (4) be transparent about #3 with all interested parties.
There are a couple of more general concepts, too. One is to date different types of people. While I have to be attracted to them, of course, dating men of different ages, looks, lifestyles and interests will challenge my notions on compatibility.
And there have been some limiting patterns. When John met a recent man I became involved with, his appropriately-timed comment was, “Well, girl, you sure do have a type.” John’s lover, Kennieth, was more direct with his description: “Heavy latin bottoms who need to be saved.” I can’t deny it.
The summer has started in earnest, and so has the dating. I can report that it’s already been pretty great. Some have been in my traditional “sweet spot,” pun intended. But I’ve also gone out with a 52-year-old and a 21-year-old. An artist and a lawyer. Tops and bottoms who happened to be white, brown, or black.
I’ve met some interesting men and had some fantastic experiences. Seeing this city through the eyes of different people has been fascinating. My circle of friends has already begun to expand.
And by raising my aim, I now see the full panorama of what is available. (A lot, by the way.) I am also reminded of what I have to offer. Within the context of misshapen relationships, it’s easy to focus on your shortcomings and forget the positives you bring to the table.
If the Summer of Dating does nothing else, it’s reminded me of who I am from the outside, not just from within. And who knows? It might just provide me with what I want… whatever that turns out to be.
