The 10 Most Sexually Unappealing Craigslist Postings

The 10 Most Sexually Unappealing Craigslist Postings

Last fall, Cracked profiled ten posts on the casual encounters section of Craigslist that were so bizarre, we couldn't help but bring them to your attention. We recently returned to the site to find more, in some cases even stranger requests for no-strings-attached nookie. Below, 10 more posts we tracked down that will leave you wondering, "What the hell is wrong with people?"

"hey guys"

Desired Demo:

Men, not necessary homosexuals, who want to sodomize a migrant worker

Quote:

"Im a construction guy really not gay...I pick this guy up to work with me he is one of those mexican waiting for day jobs in the corners and I don't think he is gay also but I give extra cash for his extra service...sweet sweet butt, I pick him up 3-4 days a week, I thought I could find some to do this with, another guy with strong dick."

What We Can Assume:

We're guessing Lou Dobbs is going to use this as ammunition in his campaign for immigration reform. Meanwhile, the construction worker in the Village People suddenly makes a lot more sense, though we still don't get the gay Indian.

Where It Went Wrong:

The photo is presumably the boner of the construction worker who posted the listing. Unfortunately, it's simply not an effective use of imagery if you're trying to attract people interested in "sweet sweet butt," or sweet sweet anything really. Also, if the listing's creator is "really not gay," he might want to think twice about soliciting men with his dong.

Why They're Not Getting Laid:

A blue collar worker who sodomizes migrant workers: Sounds like the villain from some NRA-sponsored first person shooter. We're guessing there are more armed to the hilt conservative vigilantes out there than men interested in photos of a fat, "not gay" dude's dong.

"How can I make the title stand out? How can I make you read this?"

Desired Demo:

Women interested in adultery and Arthur Conan Doyle

Quote:

"I've been on here before... never got a response... I know there are women out there who are seeking the same thrill I am... to cheat on their spouse and not get caught. I have plenty of exciting ideas... but I am not good at verbalizing them. I'm turned on by smart chicks who have a lot to say... because I'm like that. Currently reading Sherlock Holmes."

What We Can Assume:

Our friend here is no salesman. Rather than making a statement to entice the females cruising the site, he chooses instead to use the title line as a questioning meta-title that shows both desperation and a lack of creativity. It's a fitting lead-in to the actual listing, which also has a tone of desperation despite the fact that its author is married and confidently claims to be just like a gregarious woman.

Where It Went Wrong:

While some may cringe at calling betrayal a "thrill," we feel the mention of Sherlock Holmes is much more odd and off-putting. It's odd, because at no point in the century since Arthur Conan Doyle wrote those stories has the discussion of them gotten anyone laid. It's off-putting, because fans of those stories tend to be awkward teens, who are regularly ridiculed and beaten by their classmates. In any case, we have nothing but empathy for this man's wife.

Why They're Not Getting Laid:

The guy who wrote this listing reveals here that he "never got a response" to previous posts. We fully expect that trend to continue.

"Going out on a date this week Mon-Fri. anytime !!!"

Desired Demo:

Ladies that would give it up for the chance to experience the magic of a hotel room

Quote:

"I'm here on executive room minibar, cable tv, queen size bed, room service, magnificent view of SF, Hotel InterContinental...So i dun wanna waste this exclusive hotel room...If you wanna go out on date to dining, clubs, bars & followed by hot evenings at my exclusive hotel room... Then quickly get in touch with me...Luv, William."

What We Can Assume:

William demonstrates high standards by bragging that his hotel room is "exclusive." Not to be confused with most executive suites where they give your room key out to four or five different people and let you guys fight it out for bathroom privileges. He also seems to have mistaken the Bay Area for some sort of third-world refugee camp where women will have sex with pretty much anyone for food, shelter and the promise of a mini bar.

Where It Went Wrong:

Once again, the accompanying photos don't match up with the listing's supposed allure. William is trying to sell Craigslist users on his executive hotel and its magnificent view, but rather than post jpegs of the room, he opts to show off his slight frame. His sex appeal is unconventional (some might say limited), which makes us think he might be better served to use a picture of all the free shampoo and soaps instead of the close-up of his buttocks.

Why They're Not Getting Laid:

We like to cling to optimism at times like this, and thus hope that there aren't all that many women willing to take an all-expenses-paid night on the town in exchange for room service and the chance to watch Baby's Momma while it's still in theaters.

"Bored And Willing To DO Anything"

Desired Demo:

Women who would agree to sex based on hearsay about its health benefits

Quote:

"Sex is good for the brain, the body, and the mind. Can healthy organic cooking do ALL that? Nope! Sex is good for the immune system. Can yoga do that? Nope! There is no replacement for fun invigorating stimulating erotic orgasmics sex! Disclaimor: I am not a player or one-nighter. I want only one partner. And a good one too!!!! Lets sex togather!"

What We Can Assume:

That the listing's creator feels he should solicit a lover the same way most people ask a friend to be their racquetball partner. But while all the question-answer and exclamatory punctuation shows his seduction technique to be similar to that of a Bowflex infomercial, he also comes off as a sort of perverted and overbearing personal trainer, challenging women to allow him to assist them in working out their genitals.

Where It Went Wrong:

Besides the baffling image choice, it's not entirely clear where this non-player is getting the data to support his disparaging comments about organic cooking and yoga. Furthermore, it seems pretty unlikely that anyone would read this post and say, "Great. This is my chance to finally eat whatever I want and cancel that expensive Lotus Spa membership."

Why They're Not Getting Laid:

"Bored And Willing To DO Anything" might want to use his free time to come up with a more effective approach. Health-conscious females tend to read up on the subject, and probably go for sources more reliable than desperately horny guys they've never met.

"let's just say orally talented"

Desired Demo:

Women with a pulse, even obese women, as long as they're not skittish.

Quote:

"i love eating kitty i can do it for hours...im usually attracted to all kinds of women im not shallow at all i can find something beautiful about anyone so if your a bbw dont be scared...im not like every other douchebag on here i actually have a personality a great one i might add i dont plan to meet you then 10 mins later start fooling around i would like to get to know you at least a little maybe watcha a movie"

What We Can Assume:

That author of this listing has confidence in his ability to provide satisfying cunnilingus to anyone, large or small, who puts their vagina in his face. A cinema enthusiast whose photos reveal emo tendencies, he also has an open mind about what exemplifies beauty (which explains his hand tattoo and opinion that his own God-given allure could not be contained in just one photograph).

Where It Went Wrong:

The text of the listing is kind-hearted and certainly casts a wide net, but the picture of a completely serious My Chemical Romance fanboy showing off his less-than-impressive bicep clearly betrays the assertion that he is "not like every other douchebag." Alas, douchebags like this are congregating at your local Taco Bell parking lot as you read this.

Why They're Not Getting Laid:

His claim that he's talented at performing oral sex because he can do it "for hours" is not helping his cause. This would be like claiming you're a talented long distance runner because you can run a mile for hours: if it takes you any longer than seven minutes to finish, you're probably not as talented as you think.

"TONIGHT, IF UR A REALIST"

Desired Demo:

Extremely specialized lesbians attracted to narcissism

Quote:

"YOU... Not too tall 5'8...No acne please!!, No chipped, bitten nasty finger nails or toe nails and pleas maintain a mani/pedicure...not just pretty paint...I love light skinned black women, white women and erotic looking chicks...large breasts "C" and up. Pretty rack of pearly whites...you must smell amazing, dress nice and like you go out every once and a while. ME: All of the Above."

What We Can Assume:

That the listing's author has some sort of split personality as she claims to be both a light-skinned black woman and a white woman. Also, she would like to be serviced sexually by a clone of herself. And really, who wouldn't?

Where It Went Wrong:

There's nothing amiss about having standards, but this is by no means the venue to find a custom mate. If "ur a realist," you should realize that folks use this website to find a warm body to facilitate an orgasm. It's asking a little much to expect respondents to have sparkling white teeth. Just be satisfied they have teeth.

Why They're Not Getting Laid:

We don't know exactly how things work in Atlanta, but we doubt there's a large population of petite erotic-looking manicured lesbians with large breasts, both black and white skin, a perfect smile, expensive clothes and an enchanting aroma. If we're wrong, we'll gladly relocate immediately to this magical place.

"Any real chicks "UP" for a good time?"

Desired Demo:

Cocaine-using females that will overlook ill-advised tattoos

Quote:

"Booooooored as hell...got some party favors...23/m East Mesa...Please, ladies only...im fuckin' adorable... =P...cant recve texts...please be fuckin' real and unblock your number"

What We Can Assume:

The not so subtle mention of "party favors" and the emphasis on "UP" in the title means this starry-armed young man is trying to solicit women with cocaine or meth amphetamine. Though he is not explicit about what type of woman he finds attractive, we're guessing the teeth grinders who show up won't be as "fuckin' adorable" as our friend here, and might in fact be dudes with lead pipes and ski masks.

Where It Went Wrong:

First of all, this listing was posted at 12:30pm on a Tuesday. Boredom can be difficult, but there's got to a be better way to entertain one's self than searching out strangers for a cocaine party in the middle of a weekday. Furthermore, it sounds like this guy harbors some phone-related issues. Accidentally texting or leaving your number blocked might set him off.

Why They're Not Getting Laid:

Contrary to our extensive experience in the dope game (Jay Z's Reasonable Doubt and the first season of The Wire) he seems to assume that the only type of drug addict capable of picking up on innuendo are of the unarmed, disinclined to murder variety. We're thinking Twinkle Arms would be lucky if the first person to respond was the Phoenix PD.

"9 inches and a tight hole"

Desired Demo:

Transsexual job recruiters

Quote:

"looking for only passable hot sexy big booty t girl- thats looking for ongoing fun...also if you know where there is work to do- clerical or whatever also looking for a change in jobs...you wont be sorry- im versatile bottom-straight acting -good personality."

What We Can Assume:

That this gentleman is not your conventional multi-tasker. While looking for an attractive "lady" with a penis, he also inquires about career opportunities. We can only hope that when asked by a prospective employer how he heard about the available position, he responds with something other than, "Well, I met this passable big booty tranny and she thought I'd be a great fit ... "

Where It Went Wrong:

Networking is important, but there are contexts when it's not advisable--like when you're looking for a girl with a penis that will have sex with you. Also, based on our experience with clerical work around the Cracked offices, "9 inches and a tight hole" is at most only 25 percent of the job.

Why They're Not Getting Laid:

Our ven diagram of "People seeking clerical help/ Transexuals looking for straight acting dude to nail" is sadly out of date, so any speculation on our part is only accurate through the fiscal year 2006. We will say that he has a much higher probability than if he took the reverse approach and cruised for trannies on Monster.com.

"EXTREMELY GAY GUY HERE"

Desired Demo:

Homosexuals who may be unaware of Photoshop image editing techniques

Quote:

"I just currently had my prostate check and had a change of heart, women have been cruel to me and now I turn to you, my fellow swallowers, contact me if u want to have some oily wrestling fun, and by the way the picture is for fun thats not how I look."

What We Can Assume:

That if this is a legitimate post, the man who wrote it is not dealing well with some serious emotional issues. It seems far-fetched that an individual would choose to become gay after a prostate exam, even a thrilling one, but it's well within reason to believe that women may have ignored and neglected a man who suggests "oily wrestling fun" as part of his pick-up line.

Where It Went Wrong:

There's so much here that could potentially scare away even the most attention-starved homosexual, but the distorted face pics really aren't doing this guy any favors. Everyone looking to hook up with a gay man via Craigslist posts graphic photos of their junk and/or spread butt cheeks, that's how Craigslist rolls.

Why They're Not Getting Laid:

Anybody with an inkling of intuition will likely save their baby oil for someone who doesn't refer to members of their sexual orientation as "fellow swallowers."

"52 and Fat"

Desired Demo:

Men with absolutely no standards whatsoever

Quote:

"200 lbs. 5-9, tummy (4 kids)...DD, cellulite, stretch marks, wide hips...big um...yah, that but it gets tighter as I get warmed up...I have a big top but I don't like it played with (sensitive)...There is a catch...Send a pic and we'll go from there. Looking for Wed. about lunch time."

What We Can Assume:

That this woman may want to consider accentuating the positive. Personality? Hobbies? Income? Anything? We don't have high standards, honey. Work with us here.

Where It Went Wrong:

Other than the fact that pretty much every detail about this women is the antithesis of our cultural standards of beauty? How about the ominous warning that, on top of all that, "there is a catch?" The imagination wanders into dark places with that.

Why They're Not Getting Laid:

We're guessing most men moved on by the time she mentioned her cellulite and stretch marks, but those who stuck around to read the line, "wide hips...big um...yah, that but it gets tighter as I get warmed up," probably found themselves considering a life of celibacy.

If you enjoyed that, you might like Anthony's rundown of The 6 Creepiest Mail Order Bride Websites. And if you think "it gets tighter as I get warmed up" is the grossest sexual brag you'll ever hear, find out what Cher's boasting about in the Week in Douchebaggery. And if you're tired of hunting down all this Cracked material on your own, sign up for the Newsletter and receive the choicest picks of the week in your inbox every Thursday morning.

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