10 Phases of Dating – Michael’s Game


As a man with some semblance of an ego, it pains me to say this, but the male subject of this chapter, Michael, is what men and women would call “a stud.” Case in point? A female dating blogger fell victim to his slick words and dashing looks and called him Hemingway with a “mix of Mitchum and Mastroianni.”

He walks in the room dressed impeccably. His hair is perfectly coiffed with not a strand out of place; a look that, of course, seems achieved without an ounce of effort. You can’t ignore him – in any room. At 6’4” with a mixed Hispanic heritage, he’s every part the leading male sans the Hollywood credentials.

He lays his pea coat on the chair to reveal a fitted gray V-neck sweater over the crisp white collar of an expertly starched dress shirt. Then he takes a seat and glances at me with an air of cool confidence that has me wondering – who’s interviewing who?

I’m a little intimidated. It’s the first time that I’ve interviewed someone with the fear of looking like I’m asking for advice – though I assume he has plenty.

He does.

Some interviews involve a lot of pushing and pulling. This one involves a quick hand and a great deal of effort to produce legible chicken scratch. He’s not just talkative; he’s cocksure and rehearsed. He may not be right, but he’s assured nonetheless. We’re talking about being single.

“I loved being single,” he says as he looks off. It looks like he’s reminiscing. At the age of 30 and now in a steady relationship, he probably is. “Not many people can say that and mean it, though. They’re always looking for a relationship and if they’re not in one, they’re upset about it. Whether they admit it or not is a different issue.”

“For me, though, being single isn’t a negative state – you learn about other people, yourself, etc. You observe a lot. For example, if you meet 10 different girls, you may start to notice similarities in six of them; you start to see patterns. A lot of girls have their guard up, and they have no idea how obvious it is. Some just want your attention. But some are actually really cool.”

“You learn these things when you’re single because you’re actually out talking to girls. You get a clear understanding of what you like and what you don’t like.”

“For you, what did that look like?” I ask.

“I was out at happy hour two to three days a week [in 2010] and…well, a lot.”

“It’s addicting. I love the male/female dynamic. The banter, the chase, the chemistry, the back-and-forth. Getting to know that many women was good because it put me in a position of confidence to meet other women. I knew it was a phase, but I enjoyed the chase and conquer that came with it. It’s a challenge. ‘Yeah, she’s hot, but can you actually do it?’ I loved that.”

“Did you ever want more? Like something more meaningful?” I asked. It’s a subtle jab, but I want to see if he picks up on the fact that I assumed it was meaningless. He catches it and has an answer for it.

“I think it’s natural for people to want companionship, and ironically, that’s why I loved being single. You get a lot of the perks without all of the problems. It’s unnatural to want to be monogamous. You can do it, but it’s not natural. You have to teach yourself. And back then, I had no interest in learning.”

“I was probably dating and sleeping with six different girls every month, and none lasted more than a few weeks, but I didn’t care.”

The cadence of his speech is picking up now. He’s impassioned and speaking as if he’s arguing a point that was never contended.

“You want to know what the key to being single is, if you’re a guy? Don’t care. Don’t ever care. Most of the time, you will get rejected. But if you don’t care, you don’t lose anything. You just move on to the next one. You’ll strike out a few times and then get up to the plate and hit a home run.”

“When you have no fear and you don’t care, it’s amazing what happens. You want to get with the hot girl? You will get with the hot girl.”

And just as quickly as he leaps to his pedestal for that brief moment of inspiration, he steps down.

“I knew exactly where I was and exactly where I wasn’t. I never felt guilt for what I did, though, and I didn’t change my ways because I felt it was wrong. But it’s cotton candy.”

“Cotton candy. What does that mean?” I ask.

“Everyone likes cotton candy. It’s big, tasty and colorful. But you eat the whole thing over and over again and it’s disgusting. It might satisfy you sometimes, but it’ll never leave you fulfilled.”

“Does that mean you felt unfulfilled?” I ask.

He pauses. I’m not sure if he’s debating it or just thinking of the best way to respond.

“No. The thing is, I was always willing to be in a relationship, but I was never the kind of person to need one. I think a lot of people compromise way too much just to have someone; anyone. I was doing exactly what I wanted to be doing at that point. So no, I wasn’t unfulfilled.”

I wonder quietly if he’s realized how profound a statement he’s just made – at least in my eyes. Simple, yes, but the concept of knowing the difference between wanting and needing a relationship is a major one worth discussing. I decide to store it for later because, well, he’s still going.

“You look at guys like George Clooney. His whole identity is being this perpetual bachelor who beds beautiful women. Well for my co-workers? I was George Clooney. These married guys, 35 years old with two kids, they looked up to me. It was all part of the game.”

“So was it a game for you?” I propose.

“Being single is a lot like being an athlete; you have to get suited up for every game and bring your best stuff every time. You have to be ready for the cameras. You have to practice. Sometimes the game gets rained out; you get rejected. And sometimes you just get tired of it. But make no mistake – it is a game.”

He pauses.

“In some ways, I think it was addicting.”

“You have to ask yourself – do you want to go out on top, or become that old guy who stayed too long?”

It begs the question – did he change his ways because he felt he was getting old? That his window was closing? I lob the question his way.

“That was definitely part of it, yeah,” he replies. “It’s also really expensive; I was spending a minimum of $1,000 a month just to share the company of beautiful women. It was a lot of things. I guess you could call it growing up. At some point, it just got old.”

I’m a little taken back by the statement “it just got old.” Michael’s left the stamp of the self-aware bachelor with little remorse for his conquests but a keen understanding of their context. I guess I expected him to move on from it more decisively when he chose to. But he gives the impression that he was resigned to his fate, instead.

For clarification’s sake, I ask.

“Honestly, even at my “peak” I still felt loneliness. I was never unaware of the fact that people had the types of fulfilling relationships that I desired. But you have to teach yourself to want that; it’s a discipline.”

“Does that mean it’s a discipline you weren’t ready for?” I ask.

“Exactly. If a relationship is going to happen, you have to be open to it. People stop taking you seriously if it’s not your mindset.”

“But you also said it’s a discipline. How do you go from doing whatever you want with whomever you want to – monogamy?” I ask.

“Well, at first it’s discipline, but then it becomes pleasure within the discipline.”

He has an answer for everything.

“How so?” I ask.

“Well, it’s the same as a lot of other things in life. If you’re trying to lose weight, and you’re eating well and going to the gym, you start to see the results. Your body changes. You look good; you feel good.”

“Dating is the same way. You start making sacrifices for the sake of the relationship and the person you’re with. It may feel like work at first, but then you get companionship, trust, love – things like that – in return. So there’s pleasure that comes with the discipline.”

I agree wholeheartedly. And it strikes me as a bit odd that the most prolific bachelor in my book also seems to be one of the most honest and aware when it comes to love. Is that significant? Maybe. Maybe not.

But it does mean something. To me at least.

In fact, it’s the premise of the entire book.

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