Yeah, depends heavily. When I read the OP, I was reading just the guy/girl interactions and assuming this was a stable girl bitching about her boyfriend, in which case redirecting attention from the boyfriend and attaching it to you by demonstrating you're the better man isn't bad (similar to the current girl I have). If she's seriously depressed/emotional, then yes, try harder for the "connection", but I still wouldn't go too "beta" (hate the term) or the mildly craven-sounding approach of "but... but... see, *I* do those things!" (this incidentally is part of how I lost my wife after she went insane, trying to go for the "connection", which ultimately just lost her respect for me--and mine for me as well).
KS's initial "Hey listen, I know you're feeling down but you should come have a drink with me at the bar. I'll help you get your mind off things." is a great middle ground, imho.
KS's initial "Hey listen, I know you're feeling down but you should come have a drink with me at the bar. I'll help you get your mind off things." is a great middle ground, imho.