"How would an Aish Rabbi respond to Devarim 22:28-29?"
Here's the relevant verses (JPS translation):
This is obviously extremely offensive to our contemporary sensibilities, and, I would venture to say, offensive by any objective standards, even if earlier millenia did not recognize that objective truth.
But in the Ancient Near East, a woman was not much more than property, and the idea was, basically, you break it, you buy it.
But there can still be an uplifting perspective in these verses. The fact is that the Torah was progressive for the time, since that was the ANE version of women's rights and the ANE version of punishment for a rapist. And while it's difficult to claim that the message is timeless or still relevant, it's important to remember that Judaism is not Biblical, it's Rabbinic, and we certainly don't require such a horrific thing today. And Rabbinic Judaism has room to stretch and grow and change with the times. So the inspirational message in Devarim 22 is the fact that traditional Judaism was able to evolve beyond such laws and that shows its worth.