Hushed Willows Here's where you're wrong: she was already perfect.

Octavia drew back from him so Stark in turn took a step away, not wanting to make her uncomfortable. She seemed a bit off, but, maybe Tambourine had kept her up all night, or there was just so much going on - he couldn't blame her. Not really. He drew in a breath, giving a soft sigh as she seemed to work through her issues to focus on what she was saying. "It's alright," Stark soothed. "Rough night?" He would take however long she needed, he could be patient. "You wanna have something to eat, then we can take some back to him?" 

Which wasn't the same as a date. It wasn't. He wasn't gonna put moves on her, even knowing that she wasn't involved with anyone else - still he didn't want to be that guy. He wouldn't push her like that. He'd take his time. Go at a pace they were comfortable with, see if something organically came out. "Are things alright?" He asked, worrying over her.