This is part one of the two-part story of how I ended up in the Four Seasons hotel bar in the Upper East Side with a man twice my age, watching him as he slowly bled onto our corner table, causing a bright crimson stain to spread all over the white, pristine, tablecloth.

The Four Seasons Hotel Bar in New York City

When I first moved to Manhattan, I did not know anyone in it. I mean, a few classmates who had also just graduated 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 wear Panamas. And even though I hadn’t watched any “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 girls 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 (and thus, didn’t think ahead enough to save a copy of my ad for posterity), 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. (By the time such offers were extended to me, I was already jaded enough to tune them out completely.)

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 excerpts of some 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.