I operate under the assumption that he has noticed her but not the other way around. If there's not a solid reason to intervene then why bother?

On the other hand, if people are seated together, I ask one if she'd like another drink, she declines, and the gent insists, I'm not making it without her giving me the okay. Maybe she wants it or doesn't, I don't care. But I'm not forcefeeding anyone alcohol.

I don't really see the need to be so defensive unless the situation calls for it, is what I'm saying. But in my experience the guys sending women drinks are always the type that don't tip particularly well and think "I'm too nervous to approach this person, so I'm going to make the bartender do it for me," which is annoying.