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I definitely agree not to over prepare, but I find it helpful for me to think a little on the different paths they might take and have some stuff constructed so that when they inevitably do something you don’t expect, you have something close enough that you can repurpose or guide them back to a prepared path. It depends on what you’re good at. If I had to completely improv a session, I’m positive it would be rough. Others could improv entire campaigns without their players noticing.
I’m finding out from this that it’s owned by the same company but Hinge has a better formula for that kind of thing. You comment on an aspect of their profile (a picture, their response to a prompt, etc) and that gets sent to them. Then they can reply (which triggers a “match”) or not. You can also send likes without a comment but obviously that won’t be as effective.