4. You have the same conversations over and over again
“When conversing with people they see periodically, they ask them the same questions every time they greet each other. Normally it’s about the only thing that connects the two people, like where they met or where they worked together. A conversation ends up being:
‘Hey man, how’s the bank?’
‘Still, the same old shit.’
Then it’s just awkwardness. Of course a conversation isn’t going to develop this way; it’s the same routine every time you meet. You’re trying too hard. I normally greet people with something like, ‘How’s life?’ Really simple. If there’s anything they feel like talking about, they’ll segue into that. If not, they’ll turn the question back to you.
If you have nothing interesting to say, throw in something like “Did you do anything cool over the weekend?” The important thing is to not limit their responses. If you are always asking specific questions at the beginning of the conversation, it usually ends up being boring as fuck because the odds are that nothing new happened at work, nothing is new with Aunt Cindy, nothing is new at school, etc.” — bucknut4