It may seem mostly obvious where Steve went wrong, but it's just as important to take some time assessing why it was wrong. While many of his strategies might have been effective for the purpose of "winning" Shane, there is a vast difference between "winning" Shane and wining her heart. Since Steve ultimately achieved neither, it's clear that mistakes were made, but determining how and where is the key.
First of all, Shane left D.C. "to get away from [him]." She never knew where she stood with Steve and he was never around to build a solid friendship, with the potential to lead to more. Steve only bothered to pursue her once she made the choice to remove herself from the situation. With the exception of his initial attempt to win her back by flying to Denver "to change [her] mind," Steve mostly let Shane go. He waited a year and reached out to her on her birthday. But never once during the intervening time do we hear about him trying to reach out to her.
When Shane returns to D.C. and calls on him to help Phoebe, Steve has the chance to fight the war to get Shane back, which he only seems to escalate as a result of Oliver's presence. Everything Steve does is for his benefit. While he may be patriotic, he also knew that helping Shane would allow him the opportunity to be around her, and he definitely tried to use that to his advantage. Steve vetted Oliver to know with whom he was dealing, Oliver's only potential flaw the money he recently inherited. When it's clear he can't persuade Shane to reconsider him, Steve kisses her, as if that might have some impact. His other superficial efforts, being stationed state-side and offering to buy a porch swing, are also too little, too late. Shane leaves him behind again, and it seemed he graciously stepped aside.
When Steve initially indicated his appearance in Higher Ground "wasn't a personal visit" I actually believed him. I believed his intentions were to fulfill his mission objectives and restore national security. I should have been suspicious when he admitted to Oliver that he "would die before [he] let anything happen to her," but I gave him the benefit of the doubt initially---he could have said that because that's what he's trained to do, or because he would truly rather die than to see harm specifically come upon Shane. As always, we can neither "confirm nor deny" his intentions towards her.
What baffles me about Steve's actions in the intervening months is his failure to do anything definitive to answer that question. He seems secure simply having Shane within his orbit. The occasional shared laugh and glance over her shoulder is enough. In a sense he has finally "won" Shane. But he has only done so as long as a crisis persists that requires her skills.
But even when his hand was forced, Steve attempted to continue to filter his feelings for Shane through "security" and "personal" prerogatives. Steve even turned the situation on her, asking Shane to choose between "world changing work" and "a squeaky porch swing in Denver." His very last move was to say "I'm still in love with you." Instead of leading with love, he hid behind the guise of national security for three months, exposing his deep insecurity in the process. And, once again, Shane leaves him behind.
It was on this unseen field of battle, however, which Shane and Oliver were at war, the collateral damage of Steve's ill-fated campaign. And it's a battle we'll look at next week.
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