Whenever i am having a conversation be it any given, i always get the feeling that i am being boring and the other person isn't interested talking to me. Most of my conversations are random talk about events happening here and there in the world, or small talk. I end always asking 'what's up' or 'what's going on' which i think is not what i should be doing if i want to up the gear in the relationship, i want to have deeper conversations which could possibly lead somewhere or at least make it interesting and stop making me feel like a loser, any suggestions?