Summer in New York means parties on rooftops. On a Friday in June, I go to one. I meet a girl on the stairwell and help her carry up a tray of hotdogs. She’s got a jet-black pixie cut and is immediately friendly. I love immediately-friendly types. We walk up to the roof together and drink beer and proceed to spend thirty minutes talking about everything under the sun. We really hit it off.

Finally she takes a step back and stretches her neck far out over the Brooklyn horizon. “Man. I am rolling!” she says. “On what?” I ask. “Molly! It’s so good.” I’ve tried molly before, and I liked it. It makes you feel friendly. I did it once with an ex-boyfriend and we told each other we loved each other. In this moment, I feel slightly deceived. I suspect maybe this girl doesn’t know what’s she’s saying. There’s something impossibly intoxicating about believing your own well-intentioned untruths, a luxury that drugs afford. Whatever. I decide fuck it, why not believe? It’s a party and I’m an accessory to a high, and I will let the warmth wash over me. So we go on, feeding each other compliments like candy.

“You are so fun and glorious and lovely!” she chants to me. “You’re like, a gorgeous porcelain doll, I could just dress you up and put you in a window somewhere.”

I eat it up. “You too! You’re so beautiful and amazing and free, I wish I knew so many more people who could talk like this, who could just be open with each other.” And I mean it.

“Oh my god, me too. Can I just say, I feel like you are like…my person? You know when you just meet someone and think to yourself, ‘This person is for me, this person is my PERSON!’ That’s you, I knew instantly we’d get along, you’re great and I just fucking love you!”

“YES! I love YOU TOO!”

“We love each other!! This night is the best! I live for nights like this.”

We sit on the asphalt and roll around laughing and chatting and staring up at the smoky sky for a few hours, and then I take a 3 a.m.-train home sober.

*

I grew up in the Midwest, where people settle down early. A childhood friend of mine who I stopped keeping in real touch with years ago is getting married soon. She and her fiancé both have good jobs and a condo in Chicago. They’re likely registered at a handful of department stores for a series of matching home goods. For me the thought of buying real estate is beyond daunting, and I recently spent three hours on a roof telling a flying stranger how much I love her. Somewhere, at some point, our little road forked. Even though she and I are no longer close, her grown-up, happily-ever-after tale has become something of a template against which I measure the entropy of being 25 and single in New York City. It’s a reminder that the familiar safety of a happy ending is always there, like a net, if you’re willing to let yourself fall in it.

New York has no nets. You can’t be 20-something here and unaccustomed to loneliness, a natural product of a city filled with people who meet their ‘best friends’ while rolling at parties. I’m reminded of this a couple of weeks after the rooftop exchange, when I go out one night with a group of friends. We’re at a darkened club and there is a band playing. I beeline for the bar and order a beer. I scan the room and sip, and that is when I see him: my Imaginary Man.

Every boy-liking girl has an Imaginary Man. Usually a few over the course of life. He tends to be a specific type; for example, my prototypical Imaginary Man is tall and thin and sleepy-eyed. Unlike all other men, he’s not really there. This doesn’t stop you from becoming utterly infatuated, which you will. The point of an Imaginary Man is that you don’t know him and you can’t obtain him (maybe he’s mentally ill to some degree, or just doesn’t want to spend time getting to know your sorry ass). This will make you want him more. The more mixed signals , the more invested you’ll become, and the more you’ll speculate. Does he like you? Maybe he does secretly, and is too afraid to act on it. You’ll convince yourself of this, and a dozen other excuses. He may love you, even, and think of you at night or look at pictures of you in various internet corners, or hang on the 140 characters you eject daily in puffs of jokey, thinly-veiled self-consciousness. He may have panic attacks over thinking of just the right thing to say to you. Or, perhaps you’re not his type. Maybe he hates your bangs. Should you get rid of your bangs for this man? You shouldn’t, but you might. Maybe you would, if the situation arose, because you’re 25 years old and achingly pliable. Too bad you’ll never know, because you don’t speak to him that often, and again – he’s not really there.

Anyway.

This particular Imaginary Man I know through work. We used to text a bit, the type of vague is-it-or-isn’t-it texting that always ended in him dropping off and me convincing myself there was some sort of excuse other than disinterest. We’ve spent time together, but not in a bar. I have a huge crush on him for no reason, and I can’t believe he’s here. He’s alone, too. I think about one time I texted him a joke, a pretty good one, and he never responded. That was our last interaction. I decide to risk it anyway. The Imaginary Man orders me a drink and we start talking. Or at least, I start talking to him. We bounce from the status of his job (busy) to his apartment (hot) to a boss we’ve both worked for in the past (kind of a dick.) He replies in polite but curt answers and barely makes eye-contact. For example:

“Are you here alone?” I venture.

“Yeah.”

“Cool…haha, I like this band.”

“Not bad.”

“Have you listened to them before?”

“Nah.”

And so forth.

Singularity is commonly mistaken as an invitation. It isn’t. People who come to bars by themselves are usually alone by choice. This man doesn’t love me, he doesn’t read my stupid blog or Twitter, and he isn’t as excited to see me as I am him. I worry that I’m bothering him but I push anyway, pressing myself on him like a little leech, oozing charm like oil until I’m bound to slip on my own grease. It never dawns on me that maybe I dislike myself, and that is why I’m engaged in a shitty interaction with a person who doesn’t care about me instead of with a person who does. Mostly I feel a haunting drive to elicit – a feeling, a half-smile, a note of attention, anything. I wonder if all girls my age are like this. I don’t understand why this is who I’ve chosen to become as a young adult, but I can’t stop myself. The romance of striking out is a bitch of a high. The hallmark of womanhood for me is constant need; the ever-present window into our gut that we’re told exists to be filled. Imaginary Men make great space-takers. You can shape them however you like, and revel in your handiwork until the contour disappears.

But disappear it will. Five minutes into our conversation my Imaginary Man, who was never really there in the first place, excuses himself to smoke a cigarette. I watch his figure thread through the crowds, and realize he didn’t even bother with the perfunctory lie that he’d be right back.

*

I think about my friend from home, the one who will be getting married soon, and wonder how it is that two people can end up in opposite spaces. I bet her fiancé returns her calls and buys her dinner on the regular. I’d love to talk to her about her ideal expectations for love and whether he meets them or she’s had to compromise. I’d ask her if she ever looks over at him in the middle of the night and feels the horrible twinge of boredom in the pit of her stomach, that unspeakable feeling of doom that comes from impending sameness. I fear this feeling so much, I cannot bear to give it life. That might be why I spend nights at bars with Imaginary Men. I wish we were close enough to have this discussion.

And I wonder, what is it about being young and longing for people you don’t really know? How is it that some seem to escape the fate of anxiety? My rooftop friend and I fell in instant love, but really we were strangers. The Imaginary Man is imaginary. Both relationships reek of the same emptiness that’s unavoidable when you live in a world where people are content not to know each other. How well can you converse when you’re conversing with an illusion? How painful is a rejection from someone who doesn’t really exist? Some illusions are undiscerning to the point of blindness, ready to throw their arms around your neck until the high wears off because you seem interesting on a stairwell. Others go everywhere alone and blow you off for a piece of paper with a wad of tobacco.

Alone at the bar, I try to forget the Imaginary Man, but inside I sting. I wonder what would happen if I found myself in my childhood friend’s position. Engaged, registering myself at Bloomie’s for shiny new casserole tins and seeing a future in their reflections…I tell myself that’s not me, that’s a terrifying mirror of into my worst fear: mistaking boredom for security. I can only assume that she’s found something that I haven’t, but inwardly I wonder if some people are inherently unsatisfiable, and if I’m one of them. My phone buzzes and there’s a text message from a genuinely kind man I know, making jokes. I know that he likes me more and that I hold the cards. For now he’ll sit and wait for a response that will never come, or won’t come strong enough, which is ironically exactly what’s happening to me. I stare down at my beer and feel stupid.

*

The night has worn itself out and I want to leave. I find my friends again. One just ran into his ex. They went out a few times a couple of years ago. She really destroyed him in a way that only imaginary people can.

“I wish I knew what happened. I really liked her. I know we didn’t even, like, go out for that many times really, but I still really like her. I don’t know.”

“Yeah, I totally get what you mean.”

“Whatever, I don’t mind that she left, I just wish people would just say what’s going on.”

“Definitely.”

I excuse myself and step into the nighttime air. It’s drizzling. As I make my way to my train stop, I’m damp, vaguely pissed off, and sort of wondering why I’m alone. I conclude that I guess I sort of like it. On a whim I text my engaged friend. She actually calls me and we chat for a bit. It’s good to hear her voice. She tells me about wedding planning, mentioning things like linens and the DJ-or-band debate and seating arrangements for her fiancé’s aunt and cousin who don’t get along. Her marriage feels so real and adult it kind of overwhelms me. She seems really happy. I tell her I’m happy she’s happy. She gushes a thank you that feels genuine. “Han, you wouldn’t even believe it! I had no idea there was so much stuff I still have to do, but there is so much stuff I still have to do, I’m losing my mind.”

Eh, at least we have that bit in common.

Thank you, mikebaird, for the image!