Trama

Larry and Rosie O'Donnell try to court the same woman. Larry takes Leon's advice, which gives him an advantage, but he finds it doesn't always work in the long run.

Larry picks up a date at a NYC art gallery and finds that Rosie O'Donnell has picked the same woman Jane (Amy Landecker) as her date. Apparently, their common girlfriend is a bi-sexual. They both ask each other to back off, but when neither does, they decide to compete for Jane's affections. Leon drives from California to stay with Larry in NYC. Larry tells Leon about Jane being a bi-sexual. He shares that he is at a disadvantage against Rosie as he doesn't know what he is doing "down there". Leon tells Larry to come up with a plan as he is not very attractive to begin with.

Larry runs into an acquaintance from LA (Dougstein) in NYC who insists on having lunch together. Larry refuses to have lunch as they are not good friends in LA and never hang out, so why hang out now suddenly that both are in different cities. Larry makes it very clear that he doesn't want to spend any time together with Dougstein.

Larry meets Jane and figures out that Rosie took her to a Yankee game with their own box and catering etc. His takeout food from a sushi place was ruined as the restaurant failed to secure the soup properly. The next day Larry complains to the sushi place. Larry only leaves when the manager apologizes to him for the shoddy service. Larry is won over by his bow towards Larry. That day Larry again meets Rosie, who tells her she had sex with Jane and is taking her to the Tony awards. Jane loves Broadway, while Larry hates it.

Larry knows he cannot compete against the Tony awards and Broadway. Larry is ready to throw in the towel as Rosie is winning the battle handsomely. Leon tells Larry that men have penises that women do not have. He asks Larry to use his equipment to his advantage. Leon gives Larry a Viagra and that impresses Jane immensely. Now, Jane wants to cancel her date with Rosie to get another night with Larry.

In the park, Larry sees a Japanese person apologizing to another Japanese with a full 90 degree bow and realizes that the apology he got at the restaurant wasn't "proper". The Japanese person tells Larry that the restaurant manager was not sorry at all, and almost a bit dismissive of Larry. No bow would have been better than the bow he got. When Jane cancels on Rosie she suspects that Larry is taking performance enhancing drugs. Rosie is adamant that something does not add up. In the many years that Larry has dated women, not one person has praised Larry for his performance in bed.

Larry next goes to the restaurant and confronts the manager to get his proper bow, which the manager grudgingly gives. Now Larry has a date with Jane and Leon is out of Viagra. So, Leon suggests Larry buys one from a peddler in central park.

When Larry meets Jane, one of the pills falls out of his pocket and Jane finds that Larry was cheating. She breaks up with him.

Dougstein had a sandwich alone and chokes on it and lands in the hospital. Larry goes to visit him and ends up having lunch with him after all.