Well yesterday I was reminded of the proper answer...when riding 2-up, let the passenger decide (45-50 mph heavy gusts, even though 72 degs F out and not a cloud in the sky) for a "casual ride out to the Ventura coast (18 miles away).
So often in the "heat" of battle, the seasoned rider will take any challenge on without a 2nd thought, exploring our limits every now and then. It takes a 2nd or 3rd party to bring things to your attention, as you have already accepted the risks of piloting a motorcycle...being a "pack leader" we sometimes need to reminded of how far we have gone in V-Twin riding.