Jimmy Shannon is a carefree bachelor enjoying his life, his business (pool tables) and his buddies. He's had a string of girlfriends, but isn't attached at the moment. When he meets Anne, they really click, and Jimmy settles into a very comfortable and happy relationship with her. The problem is, his buddies start to one by one settle down and get married, and Jimmy knows that Anne, who very likely is "the one," is also beginning to think of getting married, though she hasn't said anything.
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Jimmy's very wealthy grandfather thinks it's high time for Jimmy pop the question, and that pressure, along with Jimmy's own sense of doing the right thing, leads him to almost propose to Anne, but he loses his nerve and though disappointed, Anne continues to see him. Then after Jimmy's grandfather dies, it is found out in the will that the only way Jimmy will inherit his millions is if Jimmy is married before he turns 30, which by then is only a day away. Jimmy knows that he loves Anne, but still can't face being a married man, so when he proposes to her, she questions him and he can't answer. Anne wants someone who DOES want to get married, so she breaks off with Jimmy and gets ready to leave the country!
In desperation, Jimmy goes to each of his old girlfriends to see if they'll marry him to help him get his inheritance, and the way each one of them reacts tells him a little bit more about himself. This eye-opening experience helps Jimmy to finally grow up and see what he's done to Anne. Meanwhile, one of his buddies has put an ad out for anyone who wants to marry a millionaire and a ton of women have shown up at the church ready to marry Jimmy for his money!