I had this really funny conversation with someone recently and I’ve replayed it in my head so many times that I know (from experience) the next time I see him I won’t be able to look him in the eyes. It’s a bummer because I think I’ve missed out on a lot of friendships/relationships by being incredibly awkward after feeling a connection with someone. Please tell me this happens to others, I can’t explain it!
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The same thing happens to me. Maybe the way to do it is to just say hi and then let them lead the conversation. Because if you lead it then you will pressure yourself to live up to the quality of the last conversation. So initially just act as if you have nothing interesting to say, then allow the conversation to build organically. Not off pressure but rather off lack of expectation, and pretty much only off what they say.
Maybe the problem is that you think people like you because of the ability to have an extraordinary conversation. But just regular, even boring sounding conversations can make the other person feel good if there is a chemistry between you guys. As friends or romantically.