I ask myself two questions:
1. Am I present here and now, with this person on this date?
2. Is my date present here and now, with me?
Or is one or both of us recalling the past, or imagining the future - flinging out past stories, or future wishes at the other person?
We all have stories about the past, and we all imagine a desired future. These are worth sharing and discovering. But a conversation continually "stuck" in the past or the future is a red flag.