And the winner is... Joshua Balvin who, in 2004, was teaching a course on Roman history at a university in a "square state":

I was asked out on a date by a student via a deaf-relay service. The operator was privy (and central!) to a very awkward rejection conversation between a teacher and his pupil.

He was always the awkward kid in class and didn't have many friends so I took a special interest in reaching out to him to make sure he felt included.

When I got the relay call, the operator sounded like she couldn't have been much older than 20 (and given that we were living in a square state at the time, clearly her first interaction with gay men). His invitation was innocent enough—going out to dinner—but (in addition to being a violation of my contract), I had zero interest.

The operator was clearly taken aback and seemed to lose her ability to talk: "Well... if Friday... we could try... another... or something." Gauging her sudden loss of facility with the English language, I can only imagine her signing must have digressed to borderline incoherence. After about 3 minutes of back and forth—clearly not going anywhere—I made up a lame excuse about getting another call.

He stopped showing up to class after that.

Awkward!

Congratulations, Joshua. Your prize is two tickets to any performance of The Callers at Washington Ensemble Theatre between tomorrow night and closing night on Feb 6. And congratulations to our runners-up Lee Osorio and Demetria Spinrad, whose stories of telephone-operator awkwardness are below the jump.

From Demetria, who worked as a telemarketer for a retirement-home finder:

I was briefly employed at a Seattle-based call center with the company A Place for Mom. APFM makes its money off seniors who are too confused or desperate to google retirement communities in their areas; it "refers" people to its partners and takes a hefty chunk of the profit.

I had to work with a program that would bring up leads for me to call. These leads were names and telephone numbers collected by aplaceformom.com or one of its shady "affiliate" websites like nursinghomes.com. Basically, these websites made you believe that you would be able to find information about local senior care places if you entered your name and number. You'd get a page with dummy numbers, all of which led back to the call center, and incessant calls from the company.

Smart people know better than to enter their name and number into an unknown website, so a lot of the places I called were spoofs, disconnected or wrong numbers. I was still required to call every lead no matter how unlikely the number looked. Supervisors listened in on calls for most of the day, so they could overhear everything employees were saying and they'd write you up if you didn't call a number.

One day, a lead pops up with the name Buttsex McGee. I call the number and a recording picks up: "Hello, and welcome to Sexy Singles, where hot local singles are available to talk right now..."

Buttsex McGee had sent me to a phone sex line.

That wasn't the only strange conversation I had there. I accidentally sent a sweet old man to a porn site (he was trying to find a video on youtube and ended up on an very different amateur video site), listened to a lady talk for two hours straight about the government chip in her brain and chatted with a very cool dude who didn't want to go into assisted living because they might not let him smoke pot there.

And from Lee, who worked as a telemarketer for the dating service Great Expectations:

When I was fifteen I needed a job, and having worked the previous summer as a Sandwich Artist in the world's grossest Subway, I was ready to move up in the world. I wanted a job in an office. I wanted to sit at a desk. I wanted a grown-up job that paid more than minimum wage. And I found just that at Great Expectations.

You are probably familiar with GE, if only because of the Mad TV parody of their services, "Lowered Expectations". It is a dating service. The idea is that you pay them an obscene amount of money to join, another arm and a leg to have a "professional" photographer snap a couple of shots for your profile which will also tell potential love matches what your hobbies are, what kind of work you do, and generally why you are the man or woman of the reader's dreams. Your profile is then put in a library. When someone sees a profile they like, you receive a call with that person's member number. You check out their profile, and if you like what you see, you go on a date that will undoubtedly lead to marriage, kids, and a white picket fence. Right?

What they don't tell you is that there is no guarantee that you will ever receive a date. Ever. (I found this part out towards the end of my tenure with the company.)

Knowing that the system was broken and that with this new thing called "Match.com" they were on their way out, Great Expectations had a stroke of genius, hire telemarketers to promote their services.

And this is where I came in. At fifteen I was offered nine dollars an hour and unlimited free coffee to talk to the single population of Atlanta every Sunday through Thursday, 5-9pm, and Saturdays 11am-2pm.

The pitch was clever. "Hi, my name is X, and I was hoping you might be willing to participate in a brief survey about what it's like to be single in Atlanta?"

"Question Number One: Are you currently seeing anybody?"

"No, I understand, it's hard to meet people (Try being a gay boy in the South, then we'll talk). How are you trying to meet people now?"

"Yeah, I also have found that bars and clubs are not the best place to meet people (Mainly because I can't get into them)"
"My mom tries to introduce me to people from church, too! (My mom hasn't stepped foot in a church since that fight with Aunt Debbie in '89)"

"Well, once a week, I mean, that's just...it's not enough, is it? (I bet you didn't wake up this morning and think, I think I'll share the intimate secrets of my personal life with a fifteen year old)?"

"Uh hunh."

"He did?"

"Aw. No. That's..."

"No, I understand."

"It does take work"

"Yes. Yes!"

"Right?"

...Half an hour later...

"Let me tell you the other reason that I'm calling tonight..." And then the pitch.

"I'm not selling anything over the phone... No, I never give my credit card out over the phone either (I don't have one to give). I just want to invite you in for a free membership consultation with one of our representatives to see if this might be a good fit for you."

"I'm with you, the internet is a scary place. You don't know if people really are who they say they are. (I've been saying I was 18 since I was 11)."

"Sounds like this might be a great opportunity for you! I'm so excited you've decided to come in. A representative will meet with you on Wednesday at 5 pm."

"No, unfortunately, I won't be here that night. It's my wife's birthday, actually. I know, we're going to the Olive Garden. Her favorite."

"Oh, don't cry. No, no, he is out there, or in here. Come in. We'll find your Mr. Right."

I did this for nine months. I spoke with people from all walks of life from the guy who's brother's wife slept with the contractor and destroyed his trust in women to the forty year old virgin who's high school boyfriend died in a car crash. It was one of the most fascinating jobs I have had to date. No pun intended. And it taught me that at the end of the day, we really are all looking for somebody to love.