The respective concerns of m4w and w4m posters on Craigslist.

What it feels like for a girl.

So hey, a reader submitted her own tale of a Craigslist encounter! That’s awesome.

If you have a story you would like me to post (anonymously), you can send it to me at Ideally a story about Craigslist but I suppose any online dating-related disasters would be fine. I know not everyone wants to bare that stuff on their personal blog.

I love how close this is to some of my own experiences. Hipster self-hatred! Disappointment! Damn right. It’s funnier than mine though. Dudes on the internet (excluding myself obv.) be crazy.

So anyway here is this cool girl’s cool story:

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The Story of N.

N. was the most attractive girl I ever met through Craigslist. And I fucked her. Or perhaps more accurately, she fucked me; but we’ll get to that.

This happened a long time ago. I always meant to write about her but for whatever reason I haven’t. That reason could be that this is not a story that makes me look super awesome (in spite of the first two sentences in this post) but it’s not as if that’s stopped me before.

Maybe in writing this I’ll figure it out. I mean, maybe this story won’t even seem that remarkable to you but it still haunts me.

Then again, there is at least one reason I can think of to explain why this yarn still strikes me as particularly memorable:

I almost die at the end.

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I'm glad that you're posting again!
So, I've met a couple of guys off of Craigslist (I was the one posting an ad) and I can tell you first hand that there is a bit of an adrenaline rush when you open up your inbox and there's 100+ replies. However, it is a very, very long process to weed out the creepos from the genuine guys who just want to meet someone new and hang out. I've been lucky enough to have met some really wonderful guys that I'm still in contact with and go out regularly for drinks with, and I've never meet any real weirdos. There was one disastrous dinner/movie date with one guy, who seemed very witty online, but turned out be a complete dud.
Point is, I appreciate your honesty when you blog, and I would like to ask you if you've ever spent a really long time chatting with someone from Craigslist, without ever exchanging pictures, met up and realized that there's absolutely no chemistry or attraction between the two of you?

Thanks for the compliments, I am in2 yr blog 2.

Glad to hear you have generally had good luck on CL. If you’ve gone through the process of screening so many people, then like me you have probably levelled up enough to be able to get a read on most people after only a few emails.

Maybe because of that, I have never been in the situation you describe: chatting for a long time without exchanging photos, then meeting. I may have done that a loooong time ago with a couple girls on AOL (holy shit) but nowadays every electronic device doubles as a camera so, c’mon.

If someone doesn’t want to send a photo out of shyness or whatever I don’t blame them, but if they wanted to meet me without me knowing what they look like? I would have to think they have something to hide. I also feel like you lose some excitement and momentum in meeting someone if you email for more than a week or two without meeting but maybe that’s just me.

And I have had several experiences meeting up with people whose photos and even personalities were misleading online. Those were duds but I learned from them and (probably) improved my screening.

Of course if a prospective date sends you a photo of a different person before you meet, what’re you gonna do.

How can you tell (or can you?) if someone is writing a Craigslist ad just to see the responses, but with no real intention of actually meeting? You spoke before about people who are just looking for an ego boost.

Short answer: You can’t tell.

Long answer: Hang on, I’m getting a beer. Long answers = beer.

You can maybe sort of tell.

There are a lot of reasons why someone might want to post in the anoynmous environment of Craigslist without intending to meet anyone. Maybe the motivation for their post, be it loneliness or boredom or narcissism or whatever, is strong enough that they want some email interaction but is satisfied at that point. Maybe they know even as they’re posting that they won’t meet anyone because they’re already dating someone, or they’re too shy to meet someone online, or… who knows?

It is an ego boost to get emails from strangers, for them to submit photos for your judgment, for them to express interest in hanging out with you or dating you or sleeping with you. That might be more of a boost than if you actually met someone. Rotten dates can certainly put a momentary dent in your ego.

There are certain types of posts that can tip you off. If someone posts stream-of-consciousness weirdness they’re probably not serious. (I did meet someone from one of those posts - I do love weirdness - but you may not be surprised that I wrote about it under the title of “Bad Dates.”) If someone posts the same thing every day or two they’re probably not serious.

If someone writes back to you but doesn’t ask many questions - i.e. doesn’t seem like they’re making an effort to get to know you - or just asks for more photos (the dreaded “pic collector”) I think you can conclude that they don’t intend to meet you.

I’m trying to imagine what it’s like from the perspective of a girl seeking a guy on CL and I assume there are added difficulties because of the volume (and, presumably, creepiness) of responses. Here’s an exchange I had with a girl a couple years ago.

Her: “its made me exhausted, its too much work answering so many emails and now I really don’t feel like meeting anyone!  My post got flagged like a day after I put it out and I didn’t even bother finding out why or reposting.  I guess I just wanted to see what happened when I posted, but I really didn’t realize all that i was asking for.”

Me: “I agree, it’s fun/flattering to have a bunch of people writing to you, but it becomes a hassle trying to write back and forth and actually trying to learn much about someone. It makes it difficult to build the momentum/excitement with one person to actually want to meet them, which is too bad, since it seems designed as an ‘easier’ way to meet someone, but isn’t after all (unless you don’t care who it is). Oh well.”

Ultimately it is just really difficult to find a quality person on Craigslist. To date, to make out with, even to buy goddamn concert tickets from. There are some (ahem) out there but it takes work to find them.

Missed Connections, Part 4?

I think I’ve un-missed another “missed connection.”

I really don’t know how I do this so often. But a girl emailed me a few hours after I posted on CL, and with some savvy internet stalking I was able to find some photos that indicate it’s probably the girl I saw on the street (despite my description being fairly vague).

Not sure whether I should write her back. She lives very near me. I think she might be too young for me. And let’s face it, I’ve had wretched luck with past MCs. 

Oh, and get this: she’s on Tumblr too. (Hers is kinda lame though.)

Your princess is in another castle.

So it’s kinda been awhile since I wrote about actually meeting a girl from Craigslist.

Not for lack of effort. But as on any dating site — and maybe even moreso on CL — a likely prospect can suddenly just disappear. There was the “ethically non-monogamous” girl who asked me out, then backed off and told me she needed to consult her girlfriend first. I never heard from her again. (Don’t you wish your girlfriend was hot like me.) There was another girl who sounded really ready to go but gave off a slightly crazy vibe, so in that case it was me backing off. There was a third girl who sounded pretty cool but was too shy to send me a photo so I’m not counting on anything there.

It often happens that after putting in all this “work” to meet someone, a new, good date option with whom it’s simple to schedule a meeting appears out of nowhere. This is precisely what happened a few weeks ago. Idly browsing the (mostly bogus/flagged/prostitute-posted) Casual Encounters ads I saw one that looked genuine and genuinely interesting. It was from a girl who suggested something along the lines of “let’s hang out on my porch and make art, maybe have a drink or a smoke and see where the day takes us.” She was speaking my language.

I was so optimistic, in fact, that I did something I never have before.

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Why Craigslist as opposed to regular dating sites?

(Thanks for following my nonsense and I. You're blog is pretty awesome and entertaining!)

Hey, thank you too!

Well, why “regular” dating sites? I know that Match and eHarmony and maybe Plenty of Fish are very popular but I’ve never looked at any of those. I could be wrong but I have impressions of each that tell me they’re not my kind of crowd.

Then there are the “specialty” sites that ostensibly match you with similarly interested or attributed people based on your religion, your money, your looks, your intelligence, your hobbies. But they don’t match my thought process in trying to find a date; I don’t want to meet just anyone, of course, but it feels odd and limiting to categorize myself in any of those ways, or to search for someone else that way.

(…I signed up briefly for something called “geek2geek” based on my crippling weakness for geeky girls but there was truly nothing positive to be found there.)

OkCupid was kinda clever and fun when I used it, though when I deleted my profile a few years ago it seemed like that site had already adopted more of a “social networking” angle with video chatrooms and personality ratings and all kinds of crazy things. Friends still tell me they’ve met some cool people on there. But even on OKC there’s the possiblity that co-workers or people you’ve dated in the past, etc. are creepin’ on your profile. I never liked that thought.

So that’s why not “regular” dating sites. Of course there are probably tons that I’ve never even heard of, and maybe some are good; I don’t know. As with most things, you try a few, see which works for you, and stick with it.

For me that has been Craigslist.

And while it sure as hell has its own negative points - as anyone traipsing through my catalogue of posts should know - it also has some unique, positive aspects.

The near anonymity is convenient. Combine it with what I’ve referred to as the “vending machine” nature of CL and it’s the On Demand menu of dates. Just post what you’re looking for and see whether someone interesting responds. If not, your ad disappears in a few days. Your cubicle neighbor, your last date, your best friend - they’d (probably) never know it was you even if they happened to read your ad. If you have inhibitions about being direct or honest about what you’re looking for on a dating site with your face plastered all over it - that’s not an issue on CL.

Which is why something like CL’s Casual Encounters section works so well. Its somewhat seedy reputation is probably deserved and I suggest that only relatively high-level Internet Wizards use it, ‘cos here there be monsters - but there are smart, attractive (ahem) people using it too. I never post or respond to anything graphic or raunchy. I just email back and forth with a girl under the assumption that if we’re both reading/writing in that section, and we’re interested in meeting each other, we are also possibly interested in having sex with each other. I kinda prefer that the subject of sex doesn’t even come up in emails before we meet; nobody can get too excited about a sure thing, after all.

I’ve written a few times about Missed Connections, and while my best result from MCs so far is one bad date, I still think this is a pretty awesome concept. Its basic premise is “What If?” and that’s kind of a running theme in the happenstance of city life. Or just, you know, life.

The sheer volume of people who could be reading your post on any given day makes the “regular” dating sections of CL a good option as well. Anyone could write to you. Any religion. Any level of intelligence. Any height. They probably will.

You can write a single sentence that makes someone out there want to know you.


The only thing worse than posting an ad and getting no responses is getting your lone non-spam response from someone you already met last year, who writes:

"Physically I’m very attractive"

(strike one)

"I’m an awful lot of fun"

(foul tip)

"I’m an awful lot of fun in bed"

(yer outta there)

To say more would be vindictive and mean, which I’m not. But I am kinda mad at myself. Still. It’s awful to be reminded that I have the first-hand experience to disprove all of her claims.

Missed Connections, Part 3

You’ve read about my “missed connection” post on Craigslist which worked. Poorly.

And then you read about two more that didn’t “work” at all, even though the girls I was looking for did email me.

So how about a MC post that someone wrote about me?

Finally, right? It only took, what, four years? During much of that time I wasn’t reading MCs because I realized that despite my initial optimism, posts about me weren’t going to pop up all over the place. But I would - and do - still check the MC section occasionally. A huge number of people are reading and posting on CL, so on any given day that could easily include someone who happened to check you out. I have no way to guess at CL’s total readership but based on the quantity of different girls who’ve written to me over the years, with very few duplicates (that is, same respondent to different ads at different times) it must be considerable.

But anyway, after a couple of successful (cough) MC posts of my own, plus my feverish monitoring of w4m MCs when I first discovered Craigslist, maybe I developed a slight sense of real-life situations that are likely to result in someone posting a missed connection. Because one day in January I checked the site as soon as I got home from work and found a post that was clearly about me.

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