Week 44: Why You Should Never Reveal Your Shortcomings in a Craigslist Job Posting

Perhaps the best job listing I ever saw was from a man who needed help scheduling a time for a doctor’s appointment. It read, “Please take a doctor’s appointment for us. Take 2-3 times from the doctor and check with me to see what works best. Once confirmed with me, confirm with the doctor and let us know.”

Now let’s break this down. This man needs to schedule a doctor’s appointment. For the average person, this is not an insurmountable task. He calls the doctor’s office with calendar open, figures out a time that works, then goes on with his day, almost as though this was a really easy task that took almost no time. Not this guy. First, this guy wanted to filter through e-mails from a bunch of people interested in working for him and find the right candidate. Then he wanted said candidate to call the office for him, find multiple times that could conceivably work, then call him back, check in on those times with him, then call the doctor’s office back, hope those times were still available, book one, then call him back and tell him that his time was successfully booked. Presumably, sometime around 11:00 that night, he would finally have himself a doctor’s appointment without all that hassle of talking to the receptionist.

At some point, you have to ask yourself, how much time are you really saving?

My job is to look for jobs. Several days a week for several years, I have sat down and combed through listings, hoping for that next column. And, as hard as this is to believe, I don’t apply for all of them. But just because I can’t apply for the jobs doesn’t mean I can’t use them in a column. So this week’s story is a handful of job postings I never applied for but that I still wanted to share. The original text of the post is in italics. While some information has been cut for spacing reasons, none of the text has been changed and everything is verbatim, because, as you will see, why edit perfection? My reactions to the gigs follow in regular font and, of course, in the footnotes.



Female needed for sexy Trivial Pursuit gig – $1000 (Boston)

I’m a mid 30s overworked finance professional living and working downtown with a fun gig to offer the right girl. I’m looking for a beautiful, refined, and fiercely intelligent girl to play Trivial Pursuit with, with cold hard cash as your prize ($1000). But we’ll play with some twists on the rules to make things more interesting:

* if you miss your question, you have to either remove an article of clothing or down half a shot of your liquor of choice.
* if you miss your question after you’ve run out of clothes, you have to either down half a shot or receive three bare-bottomed spanks.

The game finishes the usual way, when you’ve filled up your pie piece[1] with all the colors and make it to the center of the board.[2]

That’s all there is to the gig. Good clean fun. Must be attractive and fit and send a clear picture with your reply.


I think it’s safe to say that the ship sailed on “Good clean fun” with the introduction of the phrase “Three bare-bottomed spanks.” Regardless, certainly we can all agree that wanting a girl who is refined and wanting a girl willing to strip and be spanked for money are mutually exclusive goals. As are the goals of finding someone who is fiercely intelligent and someone who thinks that signing up for this is a good idea.


Also, he is consciously ignoring the elephant in the room. You can’t post an ad like this and not reveal which Trivial Pursuit genus you are using. If this is one of the newer Trivial Pursuits then this is one type of job. But if this is one of those Trivial Pursuits from 1960 with geography questions written back when West Germany was a hip, new country (I.e. if it’s the version that almost everyone has), then even the most fiercely intelligent women will find themselves naked and drunk in a strange man’s apartment faster than my ex-wife.[3]




Spread your wings and come park with us. . .[4]


Click Here to Apply Online

Ultimate Hospitality is looking for valet parking attendants to join our team of parking professionals. We have positions available in both our Hotel (shift is 3:00pm — 11:30pm) and Restaurant Division (shift is 5:00pm — 12:00am). Compensation is based upon business levels of the location assigned to you and range from $6 – $10 per hour, PLUS tips!


It takes a certain level of audacity to promote your job as a valet with the phrase “Love working outside.” Somehow, I have trouble picturing rugged, outdoorsy whitewater-rafting enthusiasts finding fulfillment parking cars.


Also, I left out the text that tells you that this is a gig in a downtown Boston shopping mall. For those of you who have never been to Boston, allow me to inform you that there is no mall overlooking a pristine body of water with elegant jagged rocks jutting out to create a picturesque companion to the beautiful blue sky.


Single girls job/personal assistant (Oceanside)

Hi! I’m gonna be blunt…I am a single guy, 33, live alone, i work a lot and I’m willing to pay…I need companionship and personal assistant combination…I don’t discriminate but you must be a female[5]…chores: cleaning, laundry, some cooking, pampering me, taking care of my need. IM LOOKING FOR A WIFE WITH A AGREEMENT. JK no marriage just the responsibilities that a homemaker wife would have…email with responses. Looking forward to meeting you

When you say, “IM LOOKING FOR A WIFE WITH A AGREEMENT,”[6] then throw in the “JK no marriage just the responsibilities that a homemaker wife would have,” you’re kind of confusing the issue. Isn’t wife with a agreement exactly what you’re looking for? Because it really sounds like it. You start off saying you need companionship, add that the applicant must be a woman and then mention taking care of your need (which just has to be your penis, right?). Anyone who would do the homemaker stuff but is disgusted by the sexual servicing part has already stopped reading this ad well before the phrase “JK.” At this point, you’ve done the hard part. You’ve admitted that you’re looking for a prostitute-housewife combo, and all the JK’s in the world can’t convince someone that this is a wholesome butler-type position. And whoever is still reading saw that and didn’t immediately ex out of their web browser to go take a shower. So why are you backing out now? For a guy who starts off by saying he’s gonna be blunt, it sounds like you’re being pretty ambiguous and not totally forthcoming. The moral, as always, never trust whatever someone says directly after they say, “To be honest with you,” or “To be blunt.”

Need Help Making a Quality Robot to Cyborg Aerial Strip Tease Costume


I am performing an aerial piece for the extreme future fest and need a quality old school robot costume that I can both wear on the static trapeze and strip off to become a semi-nude, burlesque styled cyborg. I am looking for a quality costume. Need by Dec 1. Initial thoughts are to use 80′s looking computer and electronic parts for the robot and attachable cyborg skin pieces and or body paint stencils for the cyborg part. Further creative ideas totally acceptable.

Okay, I know you think I’m going to make fun of that one, but actually it sounds pretty fucking awesome. Rock on man.


There’s a story about Ernest Hemingway, that he made a bet with a man once that he could write a novel in six words. He then took out a pen and very simply wrote, “For sale: Baby shoes, never worn.” I don’t know exactly what the stakes of the bet were, but since this is Ernest Hemingway, I’m assuming that the other guy had to buy him some amount of booze, which Hemingway immediately drank, then wrestled an alligator in the street, then wandered off to go do other awesome Hemingway things.

The fact is, there are stories everywhere, even in the headline of a newspaper listing. I saw an ad posted by a man whose pregnant wife had been out of town for a week. He was drowning handling simple tasks like doing laundry and cooking and wanted to hire someone to do the work for him. Just reading it, I knew so much about him and the fact that his wife would end up doing all the work raising that baby. Another ad simply read:


I lost weight : Need My Blazers Altered


And I instantly had a feeling of happiness for where this man was at in life. Even the ad by the guy looking for a sexy trivial pursuit partner tells a story. One of loneliness and horniness that is ultimately pretty sad. (Not sad enough to stop me from spending several hundred words making fun of the guy, but sad nonetheless). The guy afraid to contact the doctor’s office himself, I dunno, maybe that’s the story of someone who slept with the receptionist, then never called and is now afraid to talk to her.

These listings are not just ways to earn money, they are glimpses into other people’s lives. Stories of their triumphs and failures. Not every job listing may be a column. But each one is a story.


1. Please don’t let filled up your pie piece be a metaphor. Please don’t let filled up your pie piece be a metaphor. 

2. There’s a lot about this job post that upsets me, but perhaps nothing more than the fact that this guy thinks that this is the usual way for a trivial pursuit game to end. I mean what kind of animal are we dealing with here that thinks the game ends when you simply make it to the middle? 

3. Okay, fine, I don’t actually have an ex-wife, and that’s a good thing. But I often feel like I’d be a better comedy writer if I could make that kind of joke in earnest. 

4. Yup. Spread your wings and park with us. Because nothing says freedom from the grind of life like parking cars. 

5. Discrimination.

6. [sic]. A thousand times [sic].