Who assists the high-strung venture capitalist?
Harper is the 25-year-old assistant to Kirsten, a former journalist and now editor of an online sports journalism empire. Charlie is a 28-year-old assistant to the high-strung venture capitalist Rick. Both work in the same building and meet one night when their bosses need dinner. Harper has ordered dinner for herself and Kirsten but has no money to pay for it and Charlie, who was not able to order dinner for his boss, pays for it to give to Rick. After Harper tells him she will be fired if she does not return with food Charlie reluctantly allows her to take one of the meals. 
Meeting Charlie the next day to reimburse him for the cost of the food, Harper expresses surprise that Charlie would work for such an abrasive and demanding boss. Charlie reveals that Rick is well-connected and a recommendation from him would guarantee his financial success. Harper expresses her deep admiration of Kirsten and her desire to write the sort of sports journalism that would make people cry. After complaining that they have no time for personal lives, Charlie jokes that both of their bosses need to get physically intimate. Harper is initially disgusted by the comment, but after some thought plans to get their bosses together, reasoning if they are dating each other they would have less time to overwork them. Charlie reluctantly joins in on the plan.
Their initial plot to have Rick and Kirsten "meet-cute" in a stalled elevator goes awry when they are joined by a delivery man suffering from claustrophobia who starts stripping. Charlie and Harper then arrange for their bosses to sit beside each other at a baseball game, bribing the operator of the kiss-cam to pressure them into kissing. After three attempts, Rick and Kirsten kiss. They begin dating, leaving Charlie time to spend with his model girlfriend Suze, and Harper time to date.
Charlie