My sims have been having boring conversations. When I mouse over the box above, I get told that sims get bored if you keep using the same interactions. Usually, I haven't been controlling what they say, so I don't know what they're doing. As for awkward, I guess when you say something to one person, you say it to everyone in a group. And when you think about it, it is awkward being with a couple who are flirting. Two's company, three's a crowd, etc.