Roughly once a week since September “Olive,” a 25-year-old senior account executive at a downtown PR company, and “Mason,” a 28-year-old management supervisor, have made a bet to determine who will buy the other lunch the following week. On their blog,, they’ve provided details of each bet and, as a sort of bonus, reviews of the restaurants. They say they’re pretty sure their relationship hasn’t violated any company policy, but you have to wonder what their boss would think.

Here’s the September 29 bet: Will Olive make out with Mason in his office? Later Olive wrote, “So it was Friday afternoon and my stomach was in knots. Would I actually go through with it? I did a quick survey lap around the office. This was it. I walked into Mason’s office, closed the door and casually said, ‘Hello. I’m here to win a bet.'”

Olive studied journalism at the University of Wisconsin and has done a lot of blogging. Mason majored in English and philosophy at Purdue, has a master’s in Web design from Columbia College, and plays guitar in a band he says sounds sort of like Postal Service. They officially became more than friends in May but decided not to tell anyone at work. “There is certain subject matter,” says Mason, “that we don’t want to fall into the hands of our coworkers.”

“Anonymity allows me to indulge my shyness,” says Olive. “For a period of about three months, I wouldn’t even look at Mason if we were in an office-wide meeting together. When we lunched together we left and returned at separate times and ducked around corners to avoid being seen together.”

They started using code for their flirting. “It’d always be initiated by a phone call or instant message with a random work-related question like ‘Can you edit this?'” says Mason. “If he said, ‘Sure’,” Olive adds, “then no, there are other people around. But if he said, ‘Fuck off,’ then yes.”

Slowly the dallying became more daring. In the presence of colleagues one might coyly ask the other, “So, what did you do last night?” At office get-togethers they’d let each other know with a signal–like putting on a backpack–when it was time to leave. Once at a happy hour, with Olive standing next to him, Mason enthusiastically told their boss he had to get going because he had a date with a woman named Olive.

The blog seemed like the next logical step. “It just sounded like something we’d like to read,” says Olive. “And we knew it would be great fun to write.” Mason says they fantasized that “would grow in popularity to the point where our readers would not only suggest bets and lunch destinations, but also try and seek us out at restaurants” and “uncover our true identities.”

The first bets they posted were boring. Who will bowl more strikes? Who can come closest to guessing what time it is? But then: Would Olive “spill the beans” about their relationship at an office function? She didn’t, and Mason bought lunch at Grand Lux Cafe. Six readers posted comments. “Here’s hoping that fire still burns hotter,” wrote one.

In the setup for the September 29 make-out bet Olive posted, “Since the beginning of the throws”–their euphemism for both dating and getting it on–“Mason has been chomping at the bit to get my tongue in his mouth during working hours.” Mason wrote, “A tongue is only the tip of the iceberg when it comes to office shenanigans. But it’s a start. And without a start, as they say, there can never be a finish.”

For Olive to win, two things had to happen: “The french would have to last a minimum of twenty seconds and would need to . . . accelerate into what has become known in certain circles as a ‘deep french,'” and “even if it wasn’t the case, Olive would need to at least appear to be enjoying herself.”

Mason figured he’d easily win because Olive was, as she put it, “vehemently opposed” to office displays of affection. That day, Olive wrote in a later post, “the office was quiet, I was on fire, and Mason didn’t suspect a thing.” Mason wrote, “I still cannot for the life of me believe that she actually frenched me in my office. . . . She even had that ‘I just brushed my teeth in preparation for this moment’ taste.” The two posts detailing the brief but risky make-out session (and Olive’s free lunch at Volare) garnered more reader comments than any previous dare; “I’m all hot and bothered,” read one.

For the next bet Mason upped the ante by compromising their productivity altogether. He dared Olive to call in sick after a long night out. On Thursday, October 29, their firm lost a full day’s work from both of them. In fact, over the past several months Olive and Mason have spent every sick, personal, and vacation day together, about a dozen total. Mason devoted a section of one post to calling in, which he claims to have “perfected . . . into somewhat of an art form” with excuses like “I have an extremely debilitating case of tennis elbow” and “I’ve broken out in a full body rash as a result of cleaning my tarantula’s cage.”

Their latest bet concerned the company’s holiday party. Again the question was whether one would “spill the beans,” but this time both parties were certain one of them would, either by talking about it or touching the other “quite obviously beyond office etiquette.” The subterfuge had been fun, they admitted, but they’d grown weary of the game. Four readers picked Olive to lose, three picked Mason, and one predicted “a draw.”

At the party both Olive and Mason were several hard drinks deep when one of Olive’s closest work friends asked her if she and Mason were dating. Stunned, Olive said yes. Unfazed, her friend said, “I mean, pretty much everyone in the office thought you guys were dating.”

The gossip spread quickly around the party. “Many responded with shouts of personal vindication,” says Mason, “as if they had just found out who killed Laura Palmer.” The only surprise seemed to be that they’d been together since May. “We were pretty confident in our slyness,” says Mason, “but apparently the joke was on us.”

Their boss couldn’t make it to the party. “So the jury’s still out on how or even if this will affect our jobs,” says Mason. But “if one or both of us were fired, we would be forced to second-guess why we even work where we do.”

Art accompanying story in printed newspaper (not available in this archive): photo/Flynn.