I mean, I feel like you’re asking quite the progressive crowd here and probably mainly getting responses from those who have an easy answer as well.

I imagine, most people will have some conservative parts of their family, who will think lesser of them for dating a (former) sex worker.
I definitely have that. I don’t particularly care what they think, but I wouldn’t blame anyone who does care. And in particular, if you don’t know whether the relationship with that sex worker will work out long-term (so that they might become your family one day), then the shaming from your current family might not be worth giving it a try.