I'm not so sure that Harry kept proposing to Chelsy and getting turned down again and again. I followed the romance of Harry and Chelsy very closely in those years and it was incredibly rocky. Both were inclined to stubbornness and both had quick tempers.
In those circumstances it is logical to think that Harry as well as Chelsy called it off several times in those years. It's become almost written in stone since that Harry was so incredibly devoted to Chelsy that he kept proposing marriage even when it was clear (and it was) that Chelsy refuted any idea of Royal life.
However, for several years before the final break there was a pattern of breakups and reconciliations running alongside Harry's dedication to an Army career and Chelsy wishing to become a lawyer. At that stage of their lives this was also driving them apart.
So I don't believe in the multiple proposals, sorry, nor do I believe Katy Nichol's theory of one last proposal in South Africa in 2015. These two always had great fun together and there may have been a brief fling, but they were both set of separate courses in the lives then.
Cressida, as Ingrid Seward stated, became extremely upset by public scrutiny of herself, clothing, hair, shoes etc, during the two years with Harry. She quite obviously didn't want a life in the public eye.
However, I read from quite a few sources at the time that there were also quarrels over money (she didn't have any to go to various overseas venues) and a realisation between the two of them that they had little in common really. So it was a bit more complex than Cress not wanting a Royal life. There was also a strong implication from media sources at the time that Harry was eager to move on.
I never followed Harry and his previous serious girlfriends as closely as you. I tend to believe Harry may have asked Chelsy to marry him at least once or twice, or they surely discussed marriage at some point. i've seen a video retrospective on the relationship where it does mention emotional volatility between them, which is understandable because they were young and dealing with a lot in their lives. Harry, as we now know, was still dealing with grief and anger over his mother's death, and he was emotionally needy.
I've read that Harry enjoyed being around Chelsy's close-knit family (much as William loved being around Kate's family during their courtship). Indeed, Harry's military career was problematic for Chelsy, as well as the royal duties that took precedence. Chelsy is said to have been perturbed too by Harry's roving eye, and the fact she was often asked to make scheduling sacrifices, while she didn't feel Harry made enough of a commitment or showed enough consideration to try and make more time for her. Ultimately, Chelsy did not like the cameras in her face 24/7, and she also wanted the freedom to pursue a career unencumbered by royal constraints.
I've heard the same as you describe about Cressida. Frankly, in a number of public photos of Cressida and Harry together, they do not seem especially close or happy being together, regardless of whatever closeness they shared privately. In addition, Cress, as I said was on the rebound from a prior relationship with Harry Wentworth Stanley. Significantly, she returned to HWS afer breaking up with Prince Harry. Also, Cressida was said to be upset about the media speculating marriage between her and PH right off the bat, and repeatedly bringing up her mother's colorful past in the 1960s and 1970s.
... It us said both Harry and William had trouble finding women that were willing to take on Royal life. When William and Kate were on their break, that seemed clear. Not the dream of many modern women to being Cinderella.
Yes, I've heard that too, and it certainly makes sense, after everyone knows what happened to Diana. In regard to William, I recently read that William and Kate briefly split in 2004 at a time when William became interested in pursuing Isabella Calthorpe:
https://www.marieclaire.com/celebri...william-rumored-crush-kate-middleton-jealous/ scroll down
Isabella apparently did not want to become involved with William because she felt being with him would destroy the career she wanted to build... Isabella later met and married Sam Branson (son of Richard Branson). Isabella was invited to W&K's wedding in 2011, and she is reportedly friends with Princesses Beatrice & Eugenie.
Here are other discussions of K&W's brief splits in 2004 and again in 2007, when they were still young and trying to find themselves:
https://parade.com/152491/parade/wh...ke-up-in-2007-and-why-they-got-back-together/
https://www.cosmopolitan.com/uk/reports/a22771961/prince-william-kate-middleton-break-up-split/
https://www.harpersbazaar.com.au/culture/prince-william-isabella-calthorpe-17399
Both William and Harry are fortunate in finding the life partners that are right for them. Their relationship trajectories are quite different, but both couples are very well suited.