The Miss Jobless Chronicles: Desperate Measures

The Miss Jobless Chronicles is written by Caitlin O’Toole.

Arianna Huffington was on The Today Show recently discussing a HuffPo piece by Amanda M. Fairbanks. The gist of the article is that the economy is in such a horrible state that many women are relying on rich older men to pay off their college debts. (They call themselves “sugar babies”; I call them hookers.)

“Saddled with piles of student debt and a job-scarce, lackluster economy,” Fairbanks writes, “current college students and recent graduates are selling themselves to pursue a diploma or pay down their loans. An increasing number, according to the the owners of websites that broker such hook-ups, have taken to the web in search of online suitors or wealthy benefactors who, in exchange for sex, companionship, or both, might help with the bills.”

One facebook user responded almost immediately. “Thanks to the GOP and Tea Party, I'm too poor to be a sugar daddy — and thanks to Mother Nature I'm too old to be a sugar-boy. As they say, timing is everything.”

I commented on Ariana’s facebook post that this sugar parent arrangement is not exclusive to heteros — gay and lesbian sugar people are also in high demand. (No response from Arianna. Doesn’t she know who I am?)

So, given my current underemployed state, I decide I’m going to look for a sugar person, too. I know, it’s not original — but I decide to follow this rather disconcerting trend just to see what happens.

So I start doing some research. What kinds of people are looking for a sugary kind of arrangement? Are they normal people? Freaks? People like me?

I scour craigslist for other women looking for sugar mommies (I need only search for the keyword “sugar”) and find many, many far-more-serious women than I am. In every major city. (But in Allentown, Penn., there are two people in the women seeking women section who are looking for sugar babies. Should I move there?)

In New York, though, there are at least ten active “looking for a sugar momma” listings. But even the women looking for sugar mommas don’t mince their words.

“too old, wrong figure, no sugar — 30,” one ad stated. “I was way too proud, worked too hard and wasted all those years. I probably could have made a fantastic whore. Now i'm broke, unemployed, old and fat. And from actually-dating all those years, way too picky about who I sleep with.”

“Where is my sugar mama? 21,” another ad states. “Hello I'm Here looking for a companionship with a beautiful Older women that's fun caring and love to have fun. I'm 21

5'1 full of energy love to make people smile Just looking to spend sum magical days and nights wit sum 1 Interesting. i have braids and a couple of tats. Serious replies only ladies I'll be waiting. Plz no men no couples……plz send a pic an i will do da same”

The ads in all caps are placed by women who are even more desperate. Like this Los Angeles-area woman’s:


By god, I am NOT ALONE!

So I place my own fucking ad. But the difference between mine and most people’s is that I am 41; they are in their 20s. (Should I be looking for a sugar grandmommy?)

“I need a sugar momma — 41 (Brokesville),” I write. “I'm nice, cute, hardworking, nearly famous and will make you laugh in exchange for dinners out and frequent trips to the mall. I can't really cook, I clean only when I have the urge, and I rarely put out. Sound like a dream come true? Write me!”

I get two responses: “Lol” and “r u for real?”

So I amend my original post: “Sugar mommy needed — 40 (Not kidding),” I write.

My email pinged immediately!

“butch or femme?”

“I’m more like a tomboy with a nice rack,” I respond.

I feel gross for placing the ad — even in jest — and pull it down immediately.

I clearly need to find another way of supplementing my rather sad income.

Caitlin O’Toole is a New York City-based writer and editor and the creator of “The Miss Jobless Chronicles”. A native of Washington, D.C., she began her illustrious journalism career as a Washington Post paper girl and won the 1982 carrier of the year award — a plaque she still proudly displays in her teensy weensy Chelsea apartment. Caitlin’s career has been punctuated by bouts of unemployment, under-employment, and run-ins with neighborhood misfits, local bodega owners and an 85-year-old technophile neighbor named June. She’s written for Star, Parade, Sesame Workshop,, VH1, and Fox News, and has been a guest blogger for the Huffington Post. She’s also a Kardashians know-it-all, thanks to a recent freelance stint. Please send all six-figure job offers and fanmail to You can also fan Miss Jobless on Facebook.