~ A man is standing on an elevated train platform in 1940s New York City when he is hit by a flying piece of paper. The paper belongs to a beautiful woman who accidentally dropped it as a gust of wind blew it away. The same thing happens to the man when an incoming train dislodges one of his papers and blows it onto the woman's face, leaving a red lipstick mark on the paper. The man is entranced by the lipstick mark and the woman's beauty, and therefore misses her departing on the train. The man arrives at work, despondent over the fact that he will never see the woman again. That is, until, he looks out his window and sees the woman at the building across the street. After failing to get her attention by waving his arms, the man uses a stack of contracts to get her attention by turning them into paper airplanes and throwing them into her open window despite repeated warnings from his boss. Unfortunately, his efforts are met with only varying levels of failure. As he uses his last contract, he still hasn't gotten her attention, and in desperation, he uses the bright red lipstick-marked paper, although this fails as well when he drops it. The woman then leaves her office, and the man follows. Unfortunately, he fails to see which way she went, and heads home in disappointment.
It turns out many of the planes landed in a nearby alley, and when the lipstick paper lands amongst them, they rise from the ground and set off in pursuit of the man and woman. The man is covered in airplanes, and is blown towards a train station by a heavily gusting wind, the airplanes seemingly stuck to him, where he boards a train. Meanwhile, the woman encounters the lipstick airplane, and recognizing it, she follows it to a different train station, boarding a different train. The two are finally brought together, with the airplanes pushing the man out onto the same platform as the woman at a third station where both their trains stop. The two finally meet and as the credits roll, they are seen chatting happily with each other at a restaurant table.