The relationship had a bit of a slow start.
You and he hadn't quite gotten along as teenagers with a bit of a friendly rivalry forming between your two teams, but working together over the years had mended any childish rifts that might have formed. He had always flirted with you and when you'd finally had the guts to flirt back he had been flabbergasted; to have someone who he had genuine feelings for flirt back with him? Though his surprised face was cute it hurt you to realize how little Qrow clearly thought of himself if he was surprised you'd return his affections.
The courtship was drawn out over years, the friendship and trust slowly building between the two of you; you could tell Qrow had feelings for you, and you'd already admitted your own for him, but there was more to it than simply being together. He was a man who gets stuck in his head far too easily, who doesn't realize the true worth that he has no matter how often you tried to get it across to him. You communicated from time to time but your job had taken you a bit away from him and though he visited he always left before things began to feel too serious.
Qrow lived in a deep state of denial, his second favorite state to be in (the first was being drunk).
He pretended what he felt for you wasn't love, it was just extreme attraction, you were rather stunning and charming and who was he to deny being drawn to you? It would be an insult not to flirt with you. To not care about someone like you. To not think about you constantly whenever he was flirting with some random person in the bar or sleeping with someone just because he was lonely-
Okay, maybe even he couldn't live that deep in denial.
The two of you are finally and officially reunited when he comes to Mistral to talk with Lionheart and from there, it seems like fate finally takes its hold. With all the frustration being built up from the various missing hunters and huntresses, and the relief that you weren't one of them, he couldn't deny it any longer. He loved you so damn much and he wanted to be with you, more than anything he wanted to be with you, if it wasn't for his stupid semblance... He thinks he might have given the relationship a chance much sooner.
With Salem looming over you both he didn't know how much longer he'd have to spend with you but Qrow knew he had to make every moment count.
He had to.