I find the choice of Caroline's three husbands interesting. She chose Philippe Junot partly as an act of rebellion against her mother, and he did expand her horizons socially beyond what her mother felt more suitable for her, but he also shared traits of behavior and even values which she wouldn't take at the time from Princess Grace but accepted from him. He was obviously encouraging her to pursue her studies. He felt that decorum was important, once sending her back home to dress more appropriately for a lunch or dinner he had invited her to, not hesitating to call her "fatty" and asking her to lose weight, a certain kind of bullying which was probably much blunter than her mother's but ran parallel to what Princess Grace expected of her. Of course, she espoused his wild side as well, until it turned against her, but showed a real ambivalence, even in her choice of a quite older man, (almost as another parent substitute, just more fun), considering how young she was at the time. It was also a way of counterweighing the adoration she received from everyone at the time, being with a man who was not intimidated by her, her background, her family, and who had been brought up with quite a number a common values (his line of work (?) notwithstanding.)
I don't know much about Stefano because articles, etc, were not accessible to me to the same extent while she was married to him. She appeared to have become quite a different person by then, but still imitating her mother in another way by making marriage and motherhood come first and behaving in an impeccable manner, with, from what I gather, an impeccable man.
It is interesting that she did not marry Vincent Lindon. There may be a million reasons for that and I cannot speculate. But when she chose to marry Prince Ernst, she again reverted to her mother's values, (if it is true that social standing was very important for Princess Grace), placing the principality on top of the social tier in the Gotha, assuming Princess Grace's role as First lady with an absolutely legitimate title to go with it, giving birth to a royal princess, almost becoming Princess Grace in her public role , while still keeping motherhood on the forefront. Yet the same time, (and it is the pictures of Caroline dancing at the Harley Davidson event that triggered these musings), she has chosen a man who seems very ambivalent about his social position, and while bringing out the Royal Princess in her, has also brought out a more detached, looser, more individualized woman in her. She has managed to reconcile two personas and two personalities, the flawless princess her mother was, and the more rebellious younger princess she once was, a la Stephanie.