I'm on the fence about this one. I agree with
@sazc , but I also feel like those statements like, "that sounds hard," are shallow.... like they communicate, "I'm listening to humor you and let you vent, but I'm not really interested beyond just sitting here listening, and by not asking questions, I'm just waiting for you to end this line of conversation because I don't want to go any deeper." I do wonder if that is really "active" listening or not.
Before I continue, I do want to mention that guys respond to problems differently than women - men look for solutions when they communicate an issue, while women just seek to be heard and understood. I really struggled with this with my first wife and it took me a LONG time to figure it out. Women generally hate it when you try to offer them advice to solve their issues.
But having said that, where I am now is trying to find the line between just letting a woman "get it all out", vs actually actively participating in the discussion by asking questions and seeking to understand her and how she feels vs being her therapist. What I've been doing lately, and only with women I'm serious or semi-serious with, is listen, don't try to solve the problem, but ask them questions to help get them thinking and to help me understand them better. For example, let's say a woman tells you that she really seeks her father's attention, and nothing seems like nothing is ever good enough for him. You know from previous discussions that she also has a somewhat strained relationship with her mother. So I might ask her WHY, specifically, she feels like nothing is ever good enough for him. Or why she seeks validation from her father but not her mother. I might interject a similar experience or observation I have encountered in my life. I don't try to solve the issue, and don't tell her to try x or y. I also don't spend much time on these subjects and certainly don't setup a dynamic where she is always bringing her issues to me and looking for an hour therapy session. This is more like part of a larger rambling conversation between two people that could then move on to the weather or whatever. I view this as a way to understand her better and it communicates an interest in her as a person (again, only if I've determined she is relationship material).
I'd be interested to hear a woman's opinion on this though.
@sazc if a guy never really asked questions while you vented or talked about something serious (like growing up, family dynamics, etc), would that really make you feel like he understood you?