I have a close-ish friend who's a lovely person, very intelligent, interesting and just all-around nice.
One problem - she does not know how to have a conversation. Whenever I ask her questions about herself, her day or anything really, she goes off on really long monologues that end up being only very vaguely related to the original topic. It's near impossible to rebound and pick up the conversation mid-stream, because it's usually long convoluted stories that it would seem really rude to interrupt before she finishes. She does this a LOT, and on occasions I feel like checking my watch to see how long it's been since I've managed to put in a single word. I honestly don't know how she doesn't notice.
I put up with it because I otherwise really do like her, but wonder if I should tell her something. She could be such a great friend if she was just a little bit more aware of what she does and tried to reign it in. I know for a fact she'd be mortified to know she makes people (not just me) feel that way. I also know that she's been bullied at school and struggling socially in the past, and I think it could help her make friends more easily (which is something I know she really wants). But I also don't want to hurt her feelings, and I don't see a way to bring it up without making it sound like a harsh criticism.
WWYD?