Hot Girls Who’re Chill: Finding Friends on Craigslist

When I first moved to Manhattan, I did not know anyone in it. I mean, a few classmates who had also just graduated from law school and were starting jobs in the city, yes. But I didn’t have a crew, you know? A gang of girls with whom to go out on the town, or stay in and watch movies in cute pajamas. And even though I hadn’t seen the tv show “Sex and the City” yet, I instinctively knew that New York was a place best explored with a trusty street-smart group of good-looking women who can dance.

So, I went to the place that many people visit when they need a little company: Craigslist.

You can say that I was a little bit naive. I’d never used Craigslist before, but I saw that there was a category in the personals section called “Strictly Platonic.” Not just platonic, but strictly! My stringent standards for legitimacy were satisfied. I immediately hammered out an ad seeking a crew of female friends and submitted it to the site.

The title of my ad: “hot girls who’re chill (and wanna go clubbing) w4ww – 25”

I know.

I kept the ad pretty short, and I used the slightly dismissive, privileged, almost-bored tone of the kind of girl-about-town that I wanted to become, rather than my own clueless newbie voice. In the ad, I emphasized that I didn’t want any girls with drama, and ended it with something about, hey, wouldn’t it be fun to collectively turn down and laugh at scuzzy old men in nightclubs who offer to take us to St. Barts? As if, you know, that had ever happened to me.

Anyway, I got a bunch of responses, some of which I saved. To my surprise, the fake “alpha girl” positioning worked, and many girls wrote to me in that doughy, pleading manner of beta girls, and even voluntarily sent me pictures of themselves, asking me if they were “cute enough” to hang with me. Ha! If only these girls could have seen to whom they were sucking up!

Here are some examples of the responses I got:

1. The Robot

Hi there

I like your add.

I am looking to do dancing on the week end preferably Saturday. I want to have fun, go clubbing and preferably get a classy old guy with money. If that sounds good to you, let me know and we can organize stg.


I don’t know about you, but to me this sounds like an email written by a robot from the future that had been programmed to become a prostitute robot, to service the needs of lonely male robots. Like, her algorithm correctly told her what to proclaim to satisfy my criteria. But she was not programmed well enough to be able to distinguish “ad” from“add” or to know when it is appropriate to use extreme abbreviations (“stg?”). Her CPU also did not know that female humans don’t usually say “cheers” to one another.

2. The Curious Parenthetical


I saw your message on craigslist and I figure I drop you a line. I’m 25yr old STRAIGHT (but open minded) female looking to hang out with cool chicas. I get invited to parties all the time but I don’t like showing up alone or calling a guy to take me.

I’m single and looking to meet different peeps. I like clubs lounges sports bar or whatever.

I’m looking to go out tonight maybe to Justin’s for some drinks.

if your interested email me back.


Every time I read this email, my eyebrows go up at the succession of “straight” in all-caps followed immediately by the parenthetical “but open minded”, and then I can’t even really pay attention to the rest of the letter because my brain keeps shouting, “WHAT DOES THAT MEAN?” on repeat. I mean, of course, I’m all for open-mindedness and tolerance, but is that what she’s talking about? Like is she telling me that she is very, very, certain that she is straight (not that I mentioned anything about sexual orientation in my ad) but quickly wanted to add that just because she is so vehemently straight, doesn’t mean that she’s homophobic. Or is she saying that she’s straight but maybe, if the circumstances at the club are right, we should tongue-kiss in the bathroom?

Also, the “ciao” did not fit with the rest of the word choices in her email at all. Can this be another imperfectly wired robot from the future?

3. The Cute Gay Boy

Hey what’s going on? I saw your ad and it sounded cool.. actually i’m a 26 year old cute gay boy, i go to all the swank lounges and parties and usually have no trouble getting in… I pretty much fit into any scene . It would be cool to have some hottie girls to chill and drink with, im really good at hooking girls up, and def good for a lot of laughs… hit me up

To be honest, I took this at face value. Do you see anything lurking within that’s questionable or inconsistent or odd? I mean, the only thing I can see here is that he’s all about what he can offer others, so he might be a little bit too nice?

4. The Secret Sharer

God, that sounds like me…hahahaha

And that, folks, is all that she wrote! Did you read it in a raspy whisper too?

5. The Kylie Look-alike

Me: 5’5, 115, dancers body, flat abs (4 pack:), boobs, butt, light brown hair, blue eyes, people always say I look like Kylie Minogue.

I think it’s funny that she wrote “boobs” and “butt” without any descriptors. Like, it should be common knowledge that the mere act of listing body parts is a statement on the awesomeness of those body parts.

Reading all these responses of people blindly vying for my approval just because I wrote in a bitchy tone made me feel kind of weird. I felt like I would disappoint them, Wizard of Oz style, if they knew that I wasn’t as shallow and exclusive as my Craigslist ad sounded. And that I was reading their “application” emails in a shared office in a staid law firm, not in the passenger seat of a red convertible zipping back and forth between the Hamptons and Nantucket. Also, they sounded kind of pathetic and sad and I didn’t really want to hang out with them, y’know?

Then, I got something completely different.

6. The Table-Turner

if you can turn our heads we’ll consider buying you ticket to san sebastian

fashion photographer, and his eeclectic group of A list cohorts, love the company of younger women

we are considered old perhaps by your standards, mids 40?s. but to us age is but a number. extreeemly creative and artistic, very intelligent, we know the best places to see and be seen.

now granted we hang out with models and actresses mostly all of the time, at places like the hudson hotel bar, the world bar at the trump world tower, the manderin oriental hotel MoBar, the AVA lounge, the four seasons hotel 57 57 bar. so next time your at any of those places, and you see older men, in imported suits sipping sambucca with really hot young women, that would probably be us.

but if you’re 5’9? and above, 120 lbs, or less, with a face that causes traffic to come to a halt, you might be halfway to san sebastian


He correctly presumed that I would be getting a lot of responses from people hoping to be hot enough to hang out with me (heh), and he knew that the way to get a young woman’s attention was to flip the power dynamic around, and make her want to prove herself to you, to vie for your approval. So that is what he did. And it worked brilliantly.

He managed to use as many cliched phrases from “Sex and the City” as possible, and I, having never watched a single episode (in fact, for the longest time I thought the name of the show was “Sex in the City”), tender, young, innocent, simple, and stupid –-I absorbed all of this posturing with the fresh excitement, ardor, and marvel of a child brought to her first Easter Egg Hunt. Ladies and gentlemen, I believed every stinkin’, misspelled word.

Being naturally inclusive, I emailed everybody who wrote back to my Craigslist ad –yes, everybody– and suggested that we go out that very Friday night. For one shining moment, it really looked like I was about to successfully assemble a rag-tag team of loners to set out into the tumultuous high seas of New York night life, all orchestrated from the confines of my drab midtown office. What I did not know yet was that the attrition rate for group hang-outs in New York City is approximately 99%.

By Thursday afternoon, the group had dwindled down to consist of a self described “cute gay boy,” the Table Turner, and two women with AOL email addresses that described themselves as imprisoned but nonetheless ephemeral, delicate creatures. (Yet, aren’t we all, deep down, ButterfliesInACage6969!)

The Table Turner was the most chatty. He sent me a continuous volley of musings about his fabulous life:

myself and my friends are early 40?s, late 30s. professionals, CEO’s, doctors, retired pro athletes, news anchorpersons, models and actresses and the like. but when we hang out with younger women, we never get any complaints.

Less predictably:

im no rocket scientist but i am a nuclear engineer (how else do you think i could afford to hang out at the four seasons, and be a fashion photographer slash amatuer writer?)

and i can discuss anything from einsteins unfinished unified field theory to agent provacatuer.

now most of my friends are equally well versed, though i must admit, there experiences with women’s very fine lingerie (agent provacatuer) is more of a hands on nature LOL

Hold up, what? A nuclear engineer? The Table Turner might not know how to spell one of his three vocations, but he certainly knew how to solicit the, if we are to be honest, easy respect that a shiny-eyed young person who has just entered “the real world,” is ready to heap upon any authority figure with age spots. I was intrigued and delighted that a multi-talented genius was interested in hanging out with little old, trim my own bangs, can’t uncork a wine bottle without pushing numerous and sizable pieces of the eroding cork into the bottle, me.

So when the Table Turner asked me to tell him a little bit about myself, I jumped at the opportunity. And when he pretty much ignored the little bio that I had tried so hard to make sound wry, clever, endearingly cocksure, with just a hint of a geeky high school past undercurrent (basically, I tried to sound like Neil Patrick Harris), and asked if I could send a “pix” or two of myself to him, I didn’t see anything remotely suspicious about that request, and quickly sent along the most “grown-up” photograph of me that I had in my new camera phone. It pains me to share it with anyone but, here it is:

The picture I send to the Table Turner.

I know.

Anyway, by Friday night, when it looked like my electronic entourage was dwindling down into a leftover medley of people who didn’t know what they wanted to do, the Table Turner showed off his plans for the night:

im “allegedly” having dinner with 3 models from NJ, probably in Soho, then we’re off to the four seasons for after dinner drinks and polite conversation. some where along the way either a doctor friend of mine (head of surgery) or a very attractive straight japanese actor, or possibly even a retired professional athlete (if he flies in from LA) will meet up with us. (now if im lucky non of them will show up, and i will have to entertain all of them by myself, i say “let them compete” for my attention)

Holy! Color me impressed! I wanted to be friends with heads of surgery and attractive straight Japanese actors! And retired professional athletes freshly flown in from LA like some kind of delicious mango! I wanted to –and you can tell I was really clueless at this time– hang out with models from New Jersey! I took that paragraph in one breathless gulp, and excitedly scrolled down for more:

ok, let me make you an offer (that you cant refuse)

postpone your soiree my dear… (cuz no one knows exactly what they want to do anyway, and a man that doesnt have a plan for an attractive woman such as yourself is no man in my eyes) and you and i (sans the attractive models from NJ) will go to dinner in Soho…. then… the 2 of us…, head up to the Four Seasons Hotel 57-57 bar, or (and im dying to go to either) the manderin oriental hotel MoBar, or the World bar at the Trump world tower..lady’s choice of course… for polite conversation and cocktails (martini?) and my dear…if im too boring i’ll send for reinforcements, (i.e the aforementioned)

Do you see that slight of hand there, do you??! Because I didn’t. Like an idiot, I was completely fascinated by the world that the Table Turner allegedly inhabited, and I wanted to admire it from the inside, while its glittering stars spun around me like a disco ball, a world to which I, the gaping tourist, had somehow, through a recklessly-worded Craigslist ad, gained access.

Plans are made to meet at the Four Season’s bar, which is on the top floor of the hotel, on ritzy Fifth Avenue. 8 PM. In case you were wondering, by this time, I had completely abandoned any pretenses as being a queen bee / bitch / alpha female. I let my true, accommodating, self shine through, as if it was some sort of benevolent act, peppering my emails with “I’m completely flexible,” and other cringe-worthy, gaggingly agreeable, quips. Little did I know, at that early, early, hour of the long day’s journey into womanhood, that you’re not really suppose to do that; it’s boring.

Friday night, 7PM. I rush home to my brand new studio apartment, in whose fridge I keep documents, and in whose cupboards, t-shirts and sweaters. (The ice-skates go in the freezer, obviously.) I put on 4-inch knee high heels that a street photographer had once called “fuck me boots,” a black mini-skirt slightly longer than my heels, and some sort of fragment of black silk that bared one’s back and shoulders. And while it is very understandable to look at this wardrobe choice and think that my aim was to have romantic relations with the Table Turner, that wasn’t my intention at all.

Here’s what I hoped to happen: that I would sit down for a friendly chat with the Table Turner, who would realize that I was intelligent, wry, etc. (the Neil Patrick Personality Matrix), and then would invite his colorful assembly of beautiful genius friends and older, more experienced, women to join us, and at 2 AM, we would all glance at each other with sparkling eyes over the rim of our champagne flutes (we’re on a rooftop), and I would turn to the camera with one raised eyebrow and say, “Welcome to New York, cheers!” Bittersweet Symphony crescendos in the background, and the world fades to a rich, velvety, black.

Things didn’t exactly turn out as I had hoped.

I left the house wearing 4-inch black leather knee high boots and precious little else.

So, it’s 8 PM, and a taxi deposits me on Park Avenue and 57th Street. in front of this:

A smiling doorman smoothly revolves me into the hotel’s lushly decorated, empty, foyer. I am ferried, by a series of courteous nods from various hotel personnel, into the right elevator, and, finally, up to a majestic and vehemently impersonal lobby.

As the elevator doors close behind me, I catch the eye of an older, silver-haired gentleman some 20 metres directly in front of me. He is reclining on a set of black leather furniture with two younger women. The tactile softness of the gentleman –the waves in his hair, the wool of his suit jacket– contrast against the women he’s with, their angular jewelry and sharply-lined eyes. He looks like he could be a partner at my law firm, men whose nails are better manicured than mine, and after whom I totter in a constricting pencil skirt, balancing a boxful of documents in my arms, while they glide obliviously through glass doors ten steps ahead of me. He looks me over for a second, and smiles. A big, broad, unmistakable grin. It feels good to be appreciated (for what and by whom mattered less then) and, had I started drinking earlier in the evening, I might have let him beckon me towards him. Instead, walking past him and into the bar, intoxicated only by the nebulous tremors of youth, I simply returned his smile.

So, no. I did not get that the dude was with high-end escorts and the only reason he smiled at me was because he thought I was one too.

Anyway, I timidly enter the drinking area, or arena, given its monstrous size, of the Four Seaons Hotel. It is filled with round wooden banquet tables covered in heavy tablecloths, like a collection of chocolate cakes slathered in thick vanilla icing. Busy servers walk back and forth noiselessly between the tables and the bar, above which hangs a gigantic, glittering, yet somehow still conservative, chandelier.

A husky, middle-aged man in a black sports jacket, sitting alone, waves to me from a banquet table at the far corner of the room. As I weave towards him through the tables of people in the room, I notice that he doesn’t look so… friendly. I now know that he was just nervous. But at the time, I take the grimness of his expression personally, which makes me, more than ever, want to prove myself to this Craigslist stranger.

“Hi!” I squeal, falling into the chair beside him like a stuck pig. Another artifact of youth: I was always eager to reassure other people that I was harmless by acting like a total goofus.


Now that I’m close enough, it hits me: dude is old. Not Richard Gere old or Paul Newman old. No, this isn’t a young man in an old man’s body, or an old man with a young man’s body. This is simply an old man in an old man’s body. His jacket is boxy and kinda cheap-looking, his hair uncouth, his teeth sepia-toned, and his pores stretched like dadist timepieces over the over-sunned desert that was his face. No, this guy is Jack Nicholson old.

“So…” one of us says to the tablecloth.

What was I doing here? How had I gotten myself here without pausing to tell somebody of my whereabouts tonight? Oh, right. No friends.

“Would you like a drink?”


“What do you drink?”

In law school, when I first started to drink liquor, a classmate had introduced me to the cranberry vodka, which she argued was the perfect cocktail because it tastes sweet but reliably gets you drunk. So I’d been drinking cranberry vodkas for the last three years. But now that I was a lawyer in New York City, I figured that I should graduate to something less… colorful.

“A martini?”

“Gin or vodka?”


“Gin or vodka in your martini, dear?”

“Vodka,” I say because I am not really sure I’ve ever had gin before.

“How would you like it?”


“How would you like your vodka martini, dear?”

Reach into cultural reference library, volume 1986-2004, quickly scan through personal memory for clues. James Bond movies, something about shaking and not stirring, can I get away with saying that without sounding ridiculous? Did the Peach Pit serve drinks? What did Angela drink when she went out with Ricky and Rayanne? Mental review of paper placemats at Chinese restaurants with pictures of cocktails on them, maybe I should have ordered a grasshopper!

“Um… dirty?”

The Table Turner beckons a server to our table and orders two vodka martinis, dirty. The drinks can’t come fast enough, and when they are finally placed ceremoniously on the infinite thread-count tablecloth in front of me, I down mine like a champ. The Table Turner smiles at me for the first time that night, and orders another.

I will spare you the bio-emotional details of how it was that the vodka very quickly relieved me of my shyness, a process with which you are surely already familiar from personal experience. All you need to know is that, very quickly, the Table Turner and I settle on a steady rhythm of him talking at length about his accomplishments –his original career as a nuclear scientist for the U.S. government, his budding career in fashion photography, his son (who was my age, a fact that makes me feel proudly precocious), his first novel, a work in progress… you know the drill. (I didn’t.)

All the while, I slurp on an endless supply of twenty-two dollar martinis and eat vodka-soaked olives with my fingers, chewing around the core of each one as if they were small apples, and when I notice the tray of expensive mixed nuts (no peanuts here!) in front of me, I inhale those too, hungrily tossing them into my mouth as I say encouraging, affirmative things like, “Oh, really?” and, “That must have been difficult to do.”

There are certain people in this world who will unfailingly inform you, in your first conversation with them, of the geographic location in which they were raised. These people are from Texas or Brooklyn. Sure enough, after a couple of drinks, an unmistakable Brooklyn accent slips into the Table Turner’s speech, and after detailing his lifetime achievements, he points his thumb at his chest and says, proudly, apropos of nothing, “Brooklyn boy, born and raised,” as if it added a special dimension of awesomeness to him. It is true, though, that there was something that differentiated the Table Turner from the waxen figures at the other tables and from the silver-haired gentleman in the lobby. His skin wasn’t as milky.

Though definitely not as drunk as I’m getting, alcohol does loosen the Table Turner’s tongue somewhat, and he begins to speak in free verse. In one of the rare pauses in our “conversation,” he leans back in his chair, smiling with half-close eyes, and murmurs approvingly:

When you came in here…
everyone was looking at you
everyone stopped
just to
watch you
get to your seat.

It made me feel like a prized racehorse, which really isn’t that bad of a feeling, to be honest.

A few drinks later. “Look,” the Table Turner sweeps his arm across the room, at the groups of well-coiffed men and ladies-who-lunch socializing with each other at the other tables:

I got the best table in the room…
And my seat is
the Best Seat

Do you know why this is the Best Seat?
Because it’s in the corner
and I can see

all at once
It’s the Power Seat.

Now the Table Turner is starting to fray a little at the edges. Like an overstuffed rag doll whose seams are coming loose. His face has taken on an unhealthy complexion and little beads of sweat line his forehead. His body lilts, like his speech, and his breath reeks of alcohol. He puts one big hand on the table in front of him to steady himself, and closes his eyes like he’s saying a prayer.

“Are you alright?”

“I’m ah… I’m okay. I had surgery this morning.”

“Like, this morning?”

“Yeah, so I’m pretty doped up right now…” he chuckles, emphasizing the word “doped” like it’s an edgy word that all the hip young people are saying these days.

“Wait, you had surgery today?”

“Yeah, it’s okay. I’m a tough guy.”

“What did you have surgery for?” It suddenly occurs to me that I have never seen the Table Turner stand up. For all I know, he could be a merman.

He pauses a bit, then sheepishly, “My teeth.”

“Oh. You had dental work done.”

“Yeah, it was pretty major dental work though. But I wanted to see you tonight. How could I disappoint a pretty lady?”

I don’t know if it’s because he called me “lady,” or if I’ve reached that level of drunk where, for a small window of time, you see everything with abject clarity, but suddenly I am head-slammed by the real power dynamic between the Table Turner and me.

There was nothing here for me to prove and no one to prove it to. The alleged “A-list cohort” of brain surgeons and models had been a classic “bait-and-switch” trick, and even if these friends did exist, I didn’t want to meet them anymore. I didn’t need anything from this man. Rather, it was the Table Turner who had come here, post-op and woozy, to prove himself. It was he who needed to convince me, the other people in the room, but mostly himself, that he was who he wanted to be. That he had the life that he wanted to lead, the multi-stranded, multi-colored, multi-faceted life that he took pains to illustrate for me, me! A mere stranger who had the naivete to try to look for friendship in the dark alleys of the internet.

I had nothing to lose to this man. It was the Table Turner who had everything to lose if I did not smile back at him, if I put down my drink and walked out, letting everyone in the room watch as I left him there, in his pathetic little corner, tucked away from social circles he could not join. A little tangent of a man who has spent a lifetime yearning to touch a well-clothed banquet table more than once. A Table Turner that spins yarns about himself to wide-eyed children before they realize that he’s full of shit.

My body, which had been directed towards the Table Turner, to better receive his every utterance, returns back to me. I cross my arms and sit upright in my seat: I collect myself. With a cool eye, I turn to look at him and this time, I don’t even see Jack Nicholson anymore, just a sick man propping himself up with both elbows on the table. Could anything be more pathetic?

As if on cue, bright red specks appear on the section of the tablecloth under his face, seeping into the expensive fabric, and growing, via capillary action, into fat crimson droplets. Fuck me, the old man’s nose is bleeding.

He grabs a handful of cocktail napkins and, holding them to his nose, excuses himself, mumbling that he’ll be right back.

Alone at the most powerful table in the house, I lean back in my chair and stretch my arms and legs. Looking around the room again at the dull gentlemen and ladies with hideous designer bags, I am no longer impressed. Details that had been invisible to me are suddenly palpable and I can see that the dapper servers and bartenders are not restrained, just strained. Tense and tired at seeing the same old scene play out in front of them every single night. I can see the ugliness lurking beneath the decor, the significance of the smile from the silver-haired man in the lobby, the crassness of the Table Turner’s self-aggrandizement, the torpid practicality, rather than the romance, of adjoining a hotel to a bar.

By the time the Table Turner shuffles out of the men’s bathroom with an even bigger wad of paper towels held up to his face, I am already waiting for the elevator to go down.


This article was first published in Zouch Magazine.

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