[hellweaver666]

2 is an interesting one because almost every day on /r/relationship_advice there is at least one thread where someone asks what to do when they discover "the one" has kept a secret from them for a long time and now they don't trust them any more. I imagine that response would be different if someone suddenly declared that they were rich, versus that they used to be a sex worker but sudden changes in the relationship status can certainly be unhealthy in a variety of ways.

[abnercoimbre]

There's also plenty of couples from different wealth levels doing just fine. I'd say reveal it early, though not necessarily on the first few dates.