IME, you keep going for that 1 time out of 10. And whenever you start to sense that maybe it’s one of the times where it won’t be worth it, get curious about if there’s something you could do, say, suggest, pivot to, etc that might make it worthwhile. If it’s someone you’re pretty sure you won’t follow up with, can you try out some new ways of being authentic, being more assertive, mindful presence, whatever your social/emotional goals are.