those types of conversations are hell. i can never think of anything better to say than "i'm so sorry," and i always worry that they won't think i'm being sincere. i mean, you can't say something to cheer them up and you don't really want to keep talking specifically about it for fear of pushing too much, so you just end up sitting there awkwardly, hoping that they'll just start pouring their heart out and then say "thanks for listening" so you can feel like you actually did help them somehow. i would also imagine it would be much, much harder to console someone over im compared to real life.