I almost put this in relationships, but I don't think it's appropriate; this is a general problem that need not be linked to romanticism. Okay, I've learned the whole "girls don't need you to solve their problems, they just want to vent/be empowered" thing. But the problem I have is that I sometimes get genuinely interested. I was listening to a girl vent and I asked too much about the story I guess. I thought it was appropriate: I was genuinely listening, not attempting to offer advice or solve anything, and asking questions. I wasn't trying to be obtrusive, but (1) I don't think I knew she was venting, and (2) the story was pretty interesting. Finally, I got "this conversation is a lot of work, I want to hang up now." And I wasn't only asking questions. I also said things like "wow, that sounds frustrating," "I couldn't deal with that," and "geeze, what a tough situation." (Not like a machine, mind you. I said them genuinely and appropriately.) How can I be so bad at this?! Now accepting advice.