Although I'm better at communicating through writing, I still have trouble keeping conversations going online. If I have nothing interesting to say to someone, I'll usually ask about the person's day or the previous weekend. I usually don't give a crap what the person did at work or if they did anything wildly exciting over the weekend, but I don't know what else to say, and I resort to petty small talk when I want to keep a conversation going but don't know what to say. And I hate small talk, so it's kind of pathetic and desperate. Sometimes I'll want to ask them something or talk about something deeper, but I don't want to just come out and say something like "so, what's going on with you and so-and-so?" or "tell me about your spiritual beliefs" or whatever. It's an awkward conversation shift. But I don't know how to lead into it, and sometimes I'll attempt to steer the conversation in that direction but end up sabotaging my own curiosity when the conversation veers away again. (My online conversations tend to be pretty random and silly, especially with certain friends, and sometimes I like to go back and read old conversations for a good laugh.)
I just need to work on keeping conversations from sputtering out and avoiding small talk as a back-up plan.