I have a friend who is significantly older than me (a former teacher of mine). We aren't in touch with each other that often, but she was a very important person/role model in my life when I was younger and I care a lot about her. In late December, she told me via email that she had just gone through a bad breakup. At the time, I was a little surprised by the email--she doesn't often talk about personal relationships --and I think I kind of dropped the ball on the situation. I wrote back an insufficient (IMO) reply, and then a day or two later sent a P.S. saying, "If there's anything I can do, don't forget to ask." I've since learned that she's been in therapy to try to work through the situation.
I've been thinking of broaching the topic again and just saying 1) that I really felt like I dropped the ball and that 2) if she wants/needs to talk about it, I'm hear to listen (when I was young and stupid--as opposed to old and stupid, as I am now--she helped me through a really difficult romantic situation). I feel kind of awkward about it, though, for the following reasons:
1) a lot of time has passed;
2) she's significantly older than me, as I said, so it feels kind of presumptuous somehow; and
3) she really doesn't normally talk about this stuff with me, so, combined with 1 and 2, I'm not sure if it would be inappropriate to say something
OTOH, it's obviously bothering me, or I wouldn't be thinking about it months later! So...WWYD?
ETA: I'm almost certainly going to be visiting her at the end of August...maybe it would be better to talk in person? But that's a long way away, and dh will be there, so I'm not sure how it would work.