Yeah the flipside is hidden like a lot of gender stereotyping. It's always good to ask how the stereotype plays out for those that don't fulfill it. Of course we do Harry a disservice in these threads all the time by playing with these stereotypes and alluding to him being unmanly because he isn't more direct. The whole men are direct, women wait to be earned is problematic.
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.