Damsel-in-Distress!Aziraphale thoughts
I had some new thoughts while watching the Hard Times cold open (again).
As we all know, Aziraphale likes to arrange things so he can feel cared for and Crowley can save the day. And so they have excuses to meet for dates lunch random-obviously-not-fraternizing-encounters. But his elaborate schemes actually do a number of other things, too. (This is the angel who figured out Agnes Nutter's prophecies overnight. Multiple layers and convoluted ideas are right in his wheelhouse.)
He gets to play a role. This is one I've seen people also mention, and it's closely linked to him being the rescuee. But it's more than the damsel role. I don't think he always has a rescue in mind. He might have in 1793, but in 1941? Probably not. He wants to dress up in a cute outfit and take on a human character, just like his magician persona, or the investigative journalist. He's fascinated by humans and likes to try the things they do. Sometimes it even gives him a chance to do good, like being a spy and setting up a sting in 1941. (That one didn't work out, clearly, but his intentions were in the right place.) These situations are as much trying out human things as dancing and eating are. It's another way he's exploring the world.
He encourages humans to do good. By putting himself into these situations, Aziraphale gets opportunities completely outside of Heavenly assignments where he can show his support for humans doing the right thing, and even try to change the minds of people he thinks are doing wrong. He does this a lot in The Resurrectionists minisode, but he also does it during his planned historical escapades. In 1793 he points out multiple times that cutting off heads is wrong before Crowley arrives. ("That poor woman." "Dreadful mistake, discorporating me.") If he'd been dragged out to the guillotine, he'd probably have continued trying to convince the executioner to release him, or asked other humans to intervene. I don't think he'd have rescued himself until he had no other alternative. Similarly, in 1941, he joins forces with someone who is supposedly capturing the bad guys. (Yay, good humans! I'd love to help you!) And after the double-cross is revealed, he stands there at gunpoint when he could miracle himself away immediately. ("You can't kill me! There'll be paperwork.") Like he says in Edinburgh, "People get a choice." He always gives even the nasty humans an opportunity to stop what they're doing and do something good instead. Plan goes right, he does a good thing and/or gets a human to do a good thing. Plan goes wrong, he can try to change minds. He knows he can miracle his way out if absolutely necessary.
He'll get to play dress-up, do good, encourage humans to do good, get rescued, AND go on a date with Crowley. Perfection.