I am trying to create some lines through this gray area. I feel that there are times when being persistent and showing someone you are interested is attractive since to varying degrees people like being shown others find them attractive, and similarly to varying degrees like being pursued in a positive way.
Also since the two individuals will likely have their own very different lives, there is necessity I would think to have persistence in order to create opportunities for the two people to get to know each other better, otherwise they'll just see each other once and may never bump into each other again, despite there being mutual interest.
Of course the challenge can be reading whether the other person is actually enjoying the persistence, playing hard to get or just flat out getting annoyed by it. For example, I know people and I've actually done this myself sometimes, that become so nervous around a person they like that they end up acting in a rejecting way because they are so embarrassed in that moment or overwhelmed by them. Trying to decide whether this means an actual rejection or otherwise throws another spanner in the works. Or sometimes you and the other person find yourselves in an awkward situation via random circumstances (refer to any rom com for an example) which makes approaching this person a second time slightly awkward too and second guess if you're just going to make them remember the awkwardness from before.
How do I decide whether or not to be persistent in pursuing a relation with other people?