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It’s not Romantic; It’s Ridiculous: Don’t Wait 20 Years to Make a Move

I've heard of shy, but this is nuts.

I’ve heard of shy, but this is nuts.

I like to occasionally check out the West Side Rag, this local blog listing all the restaurant openings and closings and health code violations and weird crimes that happen on the Upper West Side. And I saw this story, about a woman who had a crush on a neighborhood guy when she was 19 years old and new to New York City. She thought he was so hot. She dubbed him “Teen Idol.”

And then she did not a damn thing about it for 20 years.

That’s right. The occasion for the story isn’t just that this woman stalked him all over town, but that she wistfully watched him from afar, living his life, until one day, like a year ago, she spotted him in a building where he was working, and where she would be coming regularly. So, you know, she finally got up the nerve to introduce herself. Two decades later.

And just the other day, they got married in Central Park. That’s great! It’s also a crying shame.

Seriously?! Maybe the journalist took some liberties; maybe the woman thought he was cute but wasn’t that interested. Maybe she was involved with someone else 15 of the past 20 years. The story doesn’t say.

But what I do now is this—she waited until she was 39 to grow a pair. OK, so maybe she might have made a move when she was 22, and he may not have been ready for her, or ok, they could have gotten together, had a hot thing going, and flamed out before either of them hit 30. Doesn’t matter. You can call it fate, but I call it crazy.

My problem has always been that people say, “Ah if it’s meant to be, it will be.” But I couldn’t disagree more, because that’s like playing a chess game with fate and deciding that in order to win you won’t move any of your pieces around.

(Read more of my strong feelings about fate. Strong language advisory.)

Say something! 

My question to you is this: You see someone who appeals to you, even a little? What on God’s earth are you waiting for? This city, and most cities, are crawling with people, and the continual churn of randomness of it all is such that you just may not get this chance again.

You say, “Oh but I don’t want to have to ask a guy out.” (Men, you have no excuse. Man up.) But ladies, you don’t have to do that. But you do have to swing that door open so he knows you’re there and that he’s welcome to walk through. And I can’t tell you how many times it’s paid off (many). Including my last serious relationship, which happened because I left my card behind and he followed up.

Ok, I’ll admit, even I choke sometimes: I was playing touch football in a Zogsports league as I do in the spring and fall, and I spotted a cutie, but was like, Jesus, what the hell do I do? Walk up to him at 3pm on a Sunday and ask him out? That’s weird. Hit on him in front of his friends as they change their shoes? No. So I didn’t do anything. Like a dummy.

Then…last game of the season, guess who we’re playing. Yup. It was a tense game, overtime, the whole thing. We win. Long story, I was late, so I hadn’t played this game, but you better believe I jumped in to do the whole “good game” hand shake thing. And when I got to this handsome fella, I shook his hand and smiled and said quite simply, “You’re so cute.” I said it with a big smile and a silly energy, since it was a high-energy game and I just went with it. “You’re cute, too,” he said. “Well, I regretted not telling you that the first time we played you,” I said.

His reply? “Want to get a drink sometime?”

Yes. Yes I would.

Truth is, he could have said, “Oh, that’s sweet, but I’m married,” or “Why thank you,” and then nothing. Who cares? What do I lose by doing that? Nothing. How am I supposed to know what his deal is. It’s the most blissfully ignorant moment of all. Worst case scenario? He is blushing and flattered and you made his damn day.

Bottom line: Do not wait around and stare at people from afar. Make yourself known. Or you’ll find yourself hobbling toward some old hottie in the nursing home, saying, Didn’t you used to eat at Ray’s Pizza in the 90s? And then your dentures will fall out of your head.

(Read also: How to happen to the hottest guy in the room.)

Why You Shouldn’t Believe My Instagram Feed

Team

How fun! We won! What you don’t see is how stupid and scared I felt stepping onto that field.

Don’t believe what you see on my Instagram or Facebook page.

Because it doesn’t tell you the truth. Not all of it. I’m a straight shooter, honest, direct to a fault. Anyone who knows me will tell you that I pull no punches. Shit, my whole brand is built on helping other people be authentic.

And yet, lately when I sit down with friends and colleagues, they’ve been saying things like, “Well, you’ve been busy!” and “Business must be great, right?” and I wonder where they get that information from. And then I remember: ME.

It’s not that I purposely mislead or lie. The stuff that I post is true. Things are going well! But there seems to be this outsized idea of what I’m doing compared to what I really am. To what anyone really is.

So you can’t believe what you see in my feed, and here’s why:

1. I only post pictures where I look halfway decent. My face looks fug in many of them, and you don’t know that because I don’t show you.

2. I post my own successes and usually say nothing about the other shit. OK, so I had a piece published here or was interviewed there. You don’t know the things I didn’t get or was afraid to try for.

3. You think I’m out all the time. But I’m not. In fact, I’m often right here, in my studio apartment. I like being here. Sometimes it takes great effort for me to go out, and when I do, I usually am so thrilled I’ll take pictures of whatever I’m doing.

4. You assume that because I’m single in NYC, I’m really happening. Lest you think life in NYC is a non-stop carousel of craft cocktails and sex, let me tell you: It’s not.  I spend more time doing laundry. A great Saturday is a run through the park, a visit to the farmer’s market or Sephora, followed by a nap. There are no photos of these things. Lots of times I’m home, feeling I should be out, and sometimes I’m out, and wish I could be home.

5. I’m about to go on a vacation. THIS is where things are about to go off the rails, because for many sad, stressed, or boring weeks this winter, you heard nothing from me—you didn’t know I had a breakup, or that I was lied to by an old friend. You don’t know that I look in the mirror and wonder what the hell I’m doing with my hair or my life.

But in two days, there I’ll be, waving photos of the Mediterranean at you, shoving a cocktail umbrella up your virtual nose. I’ll be on a cruise through the Greek Islands, so you can expect close-up shots of olive oil, wine, pictures of me and some friends posing on cobbled roads or laughing at something no one remembers. There will be the fancy food arranged like a still life and sunsets over the water.

Promise me you won’t turn around and chastise yourself for what “other people” are doing. Or submit to this fantasy that everyone else is footloose and fancy free while you’re trying to get ketchup stains out of a T-shirt. For years, I never took a vacation, not one. So don’t extrapolate and think that “everyone’s doing cool stuff”; they’re not. In fact, there have been plenty of times I’ve seen you running down the beach or eating a perfect picnic lunch (remember that), or looking flawless and happy and content.

We haven’t been altogether honest, have we.

Let me tell you what I’m afraid of right now as I finish packing:

  • I will bring the wrong shoes / forget a charger / run out of underwear.
  • I will miss out on something big while I’m away.
  • My cat will die while I’m away (it has happened once before).
  • I’ll suffer horrendous diarrhea. Or be constipated for days.
  • I’ll have to be airlifted out of somewhere in Croatia due to some horrible injury.
  • I’ll lose my passport / my phone / my travel companion and be crying and no one will speak English.
  • I will not be able to relax, won’t be or have any fun, and have to lie to everyone about it later.

By now you’ve likely read the absolutely heartbreaking story (“Split Image” on ESPN) of Madison Holleran, the Penn freshman and athlete who, on January 17, 2014, took a running leap off the ninth floor of a parking garage and ended her life. The fact is, Madison didn’t have some horrible secret (addiction, crime). The point the piece makes is that the too-bright artificial light of social media made her life seem darker than it was or should have been. The evidence she left on her feed shows us little but the yawning chasm between what we see and what is.

You hopefully will NOT do something so drastic as to end your life (please God no), or pick up a dangerous drug habit, or any of those things. But you may, like many, suffer despair by a thousand cuts, if you allow yourself to be seduced by what you see.

So promise me you won’t.