I like to think the ideal choice for Anne would have been taking a third option–after all, if someone isn’t doing it for you he isn’t doing it for you, and just because David was the wrong choice didn’t mean Robert would have been the right one. She was only eighteen, after all, and her older self had a point when she blamed her father for keeping her sheltered and making all her choices for her, so she didn’t have very good judgment when push came to shove. Perhaps the best outcome for her would have been to insist on education (women did have college educations in 1939, when the story began) and travel and such, to broaden her horizons and develop herself in her own right, and eventually to choose someone who had his feet firmly on the ground AND rang her chimes.
But I have come to appreciate the outcome of this. I’ve never seen the appeal of “bad boys”, and although I can appreciate the “bad-boy-redeemed-by-love-of-good-woman” story as fiction, I am glad Richard Matheson used this story to put forth the message “Listen, women, sometimes the ‘bad boy’ isn’t a misunderstood hero or diamond in the rough. More often than not, the bad boy is a weakling and loser that will never be anything but a bad MAN.”
(I also like to imagine that for all his faults, Anne’s father objected to David because he saw David’s character (or lack thereof) more clearly than Anne did–and that there was a “missing scene” right before her elopement where he said to her, “Look, sweetheart, it isn’t the fact that he’s not rich. He’s been known for losing his temper easily, drink seems to run in his family, and he’s never held a job for more than three months”–only for Anne to scoff at him.)