I once heard "creepiness" defined as "becoming invested in advance in a particular outcome to a social interaction".
In that sense, trying tricks in order to have a "successful conversation" will always fail so long as you are emotionally invested in advance in the conversation being "successful".
It's far better to be genuine and accept that you have only so much control over how things will go.
It's ok to sort of passively want things, everyone does, but the real problem is when you try to try to subtly force an outcome that isn't natural. That's when people get uncomfortable.
If a stranger is light and friendly and asks to hang out, no problem. If they start getting subtly frustrated about your response, your spider sense goes off.