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, oliveandmason.com, 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.
Best of Chicago voting is live now. Vote for your favorites »
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.”
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.”
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.”
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.”
