George and Gracie sit in the Brown Derby, waiting to have lunch with Jack Benny. George complains about jack being cheap, and his habit of not picking up the check. Jack enters, and the group start to order. To make a point with Jack, George insists on the expensive items, and when Jack steps away later, Gracie and George talk about Jack behind his back. Though George plans to make sure that Jack takes the check, Gracie tells George to pay for the check to be polite about it.
Back at home, George is still burned up over Jack’s treatment, and having to pay the check. Gracie wonders over the difference of Jack in his younger days when he wasn’t so cheap. In the old days, Jack had it all, looks, money, fame, and generous to a fault.
Gracie goes into flashback mode to relive a time before she and George were married. Jack visits with flowers, and has an expensive night on the town planned. He tells how he goes through expensive cares so quickly and even takes her for a spin in his latest new car. A Maxwell that he doesn’t plan on keeping around for long.
Gracie holds off on Jack’s proposal, and George walks in in the middle of it. The two guys bicker over Gracie, and jokes fly about their tallent and egos. George shows off by singing, Jack shows off with his violin. George clobbers Jack over the head with the violin, and Generous Jack becomes Miserly Jack. Gracie realizes that it’s all their fault that Jack is stingy. All that is needed is for George to hit Jack again.
After a talk with a psychiaitrist, George believes it just might work, if they can recreate the setting that Jack was in when he was first hit. That means convincing him that George and Gracie are splitting up, so Jack can propose to Gracie again.
The set up is staged, Gracie invites Jack over and wants to make sure he brings his violin. George steps out to give Jack time to do his thing. Jack brings flowers, at least a pack of seeds. He gets on his knees, but with more sound affects. George enters to find Jack in the compromising position, then takes a knee as well, and with as much sound affect. As an aside, they talk about the pains of growing older.
Bill Goodwin enters and sees the two gents on their knees, and jumps to his own conclusion about the situation. He is told the story of the split up, and Bill wants the chance to marry Gracie. But he goes into a commercial instead.
Back to the proposal. Jack decides to settle this with violin playing, so George whacks him. Will it work? Will Jack be generous again? Will this be the solution to make everybody happy?