How Do I Know if a Conversation Went Well?

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I have many acquaintances and some friends, but unless I'm very close to them, I have no idea how to to tell if a conversation I had with them went well. While I'm talking to the acquaintance/casual friend, I can feel like I'm in the flow of the conversation, having a good time, and there's two-way dialogue. However, when I walk away, I'm always scared...

Did I say something wrong without knowing?
Are they relieved that our conversation is over?
How many social mistakes have I just made?
Might they be angry with me?

How do I know if a conversation went well after the conversation is over?

I feel quite uncomfortable saying that because he fact is when a conversation is done, it's done. There's no point worrying about it or trying to judge it - because unless you walk away feeling like "Wow, that conversation went fantastic", you're always going to be critical.

I'm even hesitant to give advise, as I'd have a feeling you'd then be consciously looking for those signs instead of being "in the moment", which ironically the other person will likely pick up on, and will feel awkward.

For example, if the person asks you open ended questions, or gives quite extensive answers, that's a sign of enjoying your company. But then the person might not be feeling talkative at the time. They may still enjoy your company.

Analysing whether you impressed someone or not is likely to make conversations worse. Just try to have fun with chatting, and don't acknowledge your need to post-analyse, unless if you're trying to gather insight for conversing generally.

Good luck.