Never,
Based on your emotional and psychological states, you would be wise to avoid anything associated with romantic relationships right now.
Do not under any circumstances date a dub.
As you state you still have a dub mindset about such things, which means you aren't suited to have casual, physical relationships - without wanting to bring a U-haul on the 2nd date. Or at least after you've seen her naked. Both are big mistakes. People are complicated. And when I say people I mean girls. Women are extremely complicated.
And with many gulls, i mean girls, that isn't just lipstick on her beak when she shows up on your doorstep. It's also twigs and other nest building stuff.