As was said previously, generally Harry seemed more inclined to want to build up a relationship substanively and thoughtfully, over shared interests and sympathies, and definitely not directed by a programme of flash, braggadocio, and "game". I think the fact that we are able to make light of his efforts because it suited the writers that there should be a symmetry between his service and romantic advancements, should not obscure a recognition that the way he approached and dealt with others was pretty laudable. We can only speculate, but Harry likely looked to his parents as a model for how a relationship should work. Though its conclusion didn't exactly need to be spelled out, Harry could be bold and definitive as when, probably after a number of false steps over time, he unequivocally set his feelings out to Lyndsay Ballard before her second and truly permanent departure. But as always, time and circumstance were not in his favor. Ah yes..... time and circumstance.