Funny Business with Jane Wells

Feeling Like a Loser This Holiday Season? Here's How to Hire a Bigger Loser!

A friend forwarded me an ad on Craigslist which pitches the services of the greatest holiday must-have ever—a Criticism Deflector.

"Perhaps you're the least successful of a number of siblings and will be reminded of this bleak reality ad nauseam during the long weekend," the adbegan in originally pitching the service for Thanksgiving. "If you're losing sleep over the possibility of yet another Power Point presentation on the reasons why calling your life a failure is too good for you; then I can help."

The ad offers the services of a man in Asheville, North Carolina, who's willing to come to dinner with you and appear to be an even bigger failure than you are. This would make you look better.

"Don't be the most piteous person in the room, have the satisfaction of watching your pathetic proxy wear out your source of negativity."

The seller charges by the hour and offers several different packages: Loser ex-boyfriend, roommate who can't get life together, and co-worker with obvious drug/mental problems.

Too bad Thanksgiving passed. I could've used this guy.

I reached out to the seller to see if his services are still available for Hanukkah and Christmas.

They are.

I also got the hilarious back story on how the listing came to be.

"I started a blog earlier this year that centered around Craigslist postings," wrote the seller, who prefers to go by the nom de plume of H.D. Wimbledon. Turns out, Mr. Wimbledon is a former cable news anchor and reporter in Asheville who lost that job and has been making ends meet working part time at a local community college. In February, he launched his first tongue-in-cheek Craigslist postoffering free breakfast to anyone who could explain the TV show "Lost"."I HAVE seen every episode of Lost," the ad reads, "repeat I HAVE watched the entire series, I just can't tie it all together." The ad got enough buzz that one of the creators of the ABC hit show put it on his Twitter feed.

There then followed a seriesof other Craigslist offers, including my favorite, an offer of "free candy" with a photo of a seedy looking van. "Comes with complementary van ride." Wimbledon's blog got some attention, but literary agents have yet to ring the phone off the hook. So the aspiring writer continues to Tweet hilarious musings and occasionally add another listing "just for kicks and giggles." 

I don't know Wimbledon's real name, even his name on Twitter isn't completely accurate. I just know that he's a guy. I also know he likes cats, because in one email he notified me he'd be offline for a while. "I’ve got to take my cat to the vet. I’m sure you’re shocked to learn I’m a multiple cat owner."

That's funny.

As for the Thanksgiving ad, Wimbledon tells me he didn't get many bites, but he's hoping for something more substantial during Christmas. However, he's willing to be your loser companion year round "for wide variety of other occasions such as class reunions, office parties, poetry slams & winery tours."

Wow, to be the biggest loser at a poetry slam will take some work.

Questions? Comments? Funny Stories? Email