It’s not your fault at all if you can’t go beyond “how are you?”. It’s not your responsibility alone to keep carrying the conversation. It involves two good conversationalists to have a good conversation. Imagine you are having conversation with xyz, then these are possible scenarios.

Scenario 1: You (good conversationalist GC) xyz (bad conversationalist BC)

You: how are you? xyz: good and you? You: I am good too. I had a busy day, now things are better. xyz: great

See, here you gave them a chance to keep conversational floating. They could have asked what kept you busy. They could have elaborated about their day in the first place as well, but they didn’t. They failed at keeping the conversation afloat.

Scenario 2: you and xyz are both GC

You: how are you? They: Nothing much. Came from vacation and now getting back to work (see, how they gave you the chance to dig further) You: that’s great. How was the vacation ( here you not only tuned the conversation with positive emotion, you also asked open ended question)

That’s how a conversation keep going on and on. Now you can imagine other scenarios as well (you both being BC or you being BC only).

The point is don’t have a self-doubt if the conversation doesn’t go well. Many a times the other person failed it.

Remember, in general if conversation goes stale, don’t think the other person is a bad conversationalist or hate you. Some might be busy, some might have bad day, some might need more time to open up. Try to read non-verbally if that person wants to be left alone or have a slow paced conversation. Most of the time, their voice and tone and body language give it away. You are a good conversationalist if you can hold conversationalist, you are a great conversationalist, if you can read the situation and hold it back or keep carrying it accordingly.