Yesterday, I began thinking about a topic that’d never really occurred to me before:

At what point does ‘getting to know you time’ with someone of the opposite sex morph into ‘just friends?’

Is it necessary that someone exhibit explicit romantic intentions from the get-go?

And most importantly, in what time frame do you need to get things heated up before becoming permanently platonic?

My only experience with these kinds of issues occurred with a male friend of mine we’ll call Grin. Grin was, and still is, the human result of what my ideal cooked up man would be like as far as looks, nationality, personality, and intelligence. Unfortunately, a lesser version of Grin, Mr. Grey, commanded all my emotional attention at the time – so while I was interested in Grin, I felt like I had enough on my man-plate, and never really got into it. Nevertheless, we’d meet up as friends, hang out and one another’s houses, and occasionally party together.

Then we started helping each other out with some business ventures and it became clear that our relations heading anywhere near the world of intimacy would be highly inappropriate.

Then he seemed too attractive. Untouchable. It’s like when you can appreciate a piece of artwork while having no desire to buy it. At a certain point, the romantic tension snapped and ceased existing.

Then we crossed that line and started telling each other about our love lives. For Grin, his obsession with this woman named Giulia who only lived in New York part time and who I saw as painstakingly average and uninteresting. For me, my rocky relationship with Mr. Grey, who he also knew.

The moment that our rubber band of romantic tension didn’t just snap, but got swept under the rug and forgotten, was when I met Giulia. Grin had made me aware that the woman he liked would be coming out with our group of friends that night. I chit-chatted with Giulia at the bar for twenty minutes thinking the entire time that Grin’s wonder woman had yet to arrive. It never occurred to me that my ‘perfect’ man would be interested in a woman who could be categorized as average. I expected a Giselle look-alike to saunter through the door.

This is when attraction didn’t just die, but got murdered and stepped on.

Men: I don’t think you realize how much other women define you by the woman you have on your arm. Shallow, but true.

It’s like when one of your male friends is dating a poll dancer with acrylics. You think – “Oh! That’s what he’s looking for? Really?” His stock plummets in a crash that’s impossible to recover from. You’ll never look at him the same way again.

When I saw that Grin’s obsession was a clearly very nice, but not an attractive, employable or exceedingly interesting woman, his transformation into ‘normal guy’ instead of ‘guy of my dreams’ was complete. Who am I to judge her? Giulia may be a fantastic individual, she just wasn’t what I was expecting.

Grin and I are close friends to this day, yet I still stop to wonder if we could’ve been the incredible power couple that exists in my mind. We were both attracted to one another, but somehow we missed the romantic boat. It’s like we had tickets for the cruise but ended up running around the marina lost for six hours. The timing was off and I guess my initial statements query if there’s a concrete time frame is for love.

Two weeks?

Two months?

Who makes the first move?

And why is making that move after you've got to know each other so much scarier than making a move with someone who you’re just lusting after?

I guess because when you’ve come to know and appreciate one another, there’s so much more at stake. Sometimes so much at stake that you’d rather keep the person in your life as a friend as opposed to losing them in a romantic tragedy.

Obviously, you want to get to know each other first.

Obviously, you don’t want to get to know each other so well that the thought of kissing the other person feels like incest.

It’s a rainy Thursday and as I sit here with a steaming hot chocolate, complete with mini marshmallows (yes I’m still five), it seems the perfect opportunity to reflect on the other immature aspects of my life. Yep, you all guessed right. I’m ranting about grey relationships yet again. Cut me some slack. Today the sky’s grey, the rain’s grey, my sheets are grey (they used to be white, I need to wash them, I realize that’s gross). Grey is inevitably on my mind. So using my Milanese ex-fantasy man Grin as an example, I’m going to go over some of the common symptoms that stem from dysfunctional big city relationships, all of which I suffered through with him, some of which still plague me now:

1. The Silent Treatment: Remember that game you used to play at age eight when after losing a fight with your brother or sister (usually over some glossy toy or gross piece of play dough) you’d give them the ‘silent treatment’ until your bruised ego felt like it had ‘punished’ them for an adequate amount of time? While we’re no longer playing with Barbie’s (hopefully), we still treat our grey relationship partners in the same irrationally emotional way we did our siblings. By not calling them, not texting them, not emailing them you’re both protecting yourself from being hurt when they potentially don’t respond and winning in the infantile ‘silent treatment game’ sense of victory. This transitions beautifully into our next symptom.

2. Playing to Win: Often when I post about grey / faux relationships, I’m surprised to receive reader comments encouraging me to confess my true feelings for my partner, talk it out with him, take it to the next level – all reasonable suggestions if one’s goal was to live happily ever after or fall in love. I feel in all my writing about this topic, I’ve evidently failed to properly illustrate on what a high level of immaturity the grey dynamic operates. Stability, normalcy and happiness aren’t the goals here. People in grey relationships are too afraid to fall in love. They’re terrified of living happily ever after. Happily ever after, despite its charming connotations, is frighteningly final, and grey relationship participants tend to be commitment phobic. The implicit goal may be to get closer to another human being, but the explicit goal is to win. The dysfunctional relationship rule book clearly states that whichever entity appears to care less about the relationship is considered the winner. Let’s look at an example:

After five days of giving one another the silent treatment, Grin texts me for an aperitivo. Grin initiated contact (+10 points for me) with a detailed plan for getting together as opposed to a vague ‘how are you’ (an additional +15 points for me). He’s putting himself on the line.

I happen to be busy that night (+12 points for me – I’m seemingly not prioritizing him), but phone to thank him for the invite (phoning means reaching out / caring so minus 15 points for me, + 12 points for him.)

The ultimate goal is to keep both our scores equal. If one person seems to care more than the other, things get unbalanced and someone tends to freak out and disappear. The grey relationship is destroyed. Ideally, both your scores rise at a matching rate (I mean if your scores didn’t rise you’d never see one another at all.)

So while this game may seem cruel, it’s actually a process of you both nurturing for your faux relationship so it can continue to exist at a level of intimacy you’re both comfortable with. And while the whole score keeping thing may seem confusing, it’s actually not at all. Most 21st century Manhatteners are capable of making virtually all of these calculations subconsciously. Often I don’t even think we know we’re doing it, but in a grey relationship, someone’s always keeping score. There is self-imposed control. I mean, if you just let things just play out naturally you might find yourself actually being intimate with someone (God forbid!), which in the dating game of most major metropolises is a no-no.

3. Pacing Intimacy: Pacing intimacy has a lot to do with knowing how to properly keep score. It also requires obeying certain boundaries, some of which I explored in Please Don’t Be Nice. Even though you may be crazy about this person, you have to keep in mind that you’re not each other’s significant other. The grey relationship is about fun, excitement, adrenaline, and intensely high doses of middle school cattiness. It’s not about companionship. Your partner cannot become to ‘real’ to you. I mean if you start shoe shopping together you’re just a hop, skip and a jump away from him farting in your face and you no longer shaving your legs. Or as a friend of mine put it:

“If you spend more than fourteen consecutive hours together, you’re fucked.”

Fucked in what sense? You may thoroughly enjoy each other's company, but going out to dinner or brunch several days a week is just crossing a line. You might actually start to feel like boyfriend and girlfriend (again, God forbid).

4. Hide and Seek: And because there are so many questions you’d like to ask your grey relationship partner, but know you can’t (doing so would obliterate the cloudy grayness in which you both feel comfortable), you try to attain knowledge about them indirectly from other sources. Like:

My friend (casually): Hey, you know I ran in Grin the other night at Pacha.

Me (suddenly sweating bullets): Wait. When? Where? At what time exactly? Who was he with? A girl? Several girls? What was he wearing? Dressed down or dressed up? Did he ask about me? Was he wearing jeans or dress pants? What was your exact conversation word by word? Tell me Godammit!!!!

Since I’d often be paranoid Grin was out partying when he claimed to be at home, I’d go out when I’d normally stay in and go to as many Milanese clubs and bars as physically possible with our common friends, scouring each location to make sure he wasn’t there. He never would be and I’d come home, exhausted but victorious. Mature, right?



And at the end of the day, I think one of the reasons dysfunctional relationships are so common is that they allow us to recapture the joys of childhood immaturity. These adrenaline-based affairs may be absurd, but they help us feel like kids again. The relationship games we play are rarely stressful, they’re somehow as relaxing and familiar as a game of tag, a battle of hide-and-seek.

So far, that’s the only explanation I’ve come up with about why we keep coming back for more.